Month: November 2022

Improved performance and reduced emissions in a direct injection diesel engine by fuel additives was written by Sharavanan, Ar.;Jaishanker, D.;Saravanan, C. G.. And the article was included in Society of Automotive Engineers in 2001.Related Products of 112-59-4 The following contents are mentioned in the article:

Diesel engineers are major sources of prime movers, which are widely used for small and large-scale power generation and transportation purposes. These engines are widely used owing to its high power output and general thermal efficiency. In spite of these benefits diesel engines cause serious environmental and human discomforts on global scale. The important pollutants from a diesel engine are NO_x HC and particulate matter. These particulates are inhalable, capable of traveling deep into lungs and causes diseases. As a result of this governments and health organizations have tightened the standards for pollutants from diesel engine. Hence it has becomes important that these particulate matter have to be reduced or eliminated from the exhaust f diesel engine. This project aims to reduce the particulate emission in the diesel engine exhaust and to improve the performance of the engine. A literature survey was conducted revealed that using fuel additives, which oxygenate the fuel and reduces the emissions, can reduce the particulate emission. Additives like Ethylene glycol di-Me ether, Diethylene glycol di-Me ether, Diethylene glycol di-Et ether, Bu ether, Aliphatic alc., Aromatic alc. and Glycol ethers were used by various researchers in this field, as fuel additives. Encouraging results were obtained and some of them are reported in this project. In this oxygenates, ethers behave better than alc.’s. Hence for this present work some of the ethers were selected which were not much tried and detail were not much known. Three additives were selected for the fuel. Diethylene glycol mono Bu ether, Diethylene glycol di-Bu ether, and Diethylene glycol mono-n-hexyl ether ether are the additives selected. A single cylinder direct injection diesel engine (Greaves cotton engine) was selected for conducting the tests. These oxygenates were added in different quantities to the selected base fuel, diesel. Load tests and speed tests were conducted first with the sole fuel (diesel) and then with the smoke emissions were deduced to a very great extent, the maximum reduction was obtained while using 4ml of Diethylene glycol mono-n-hexyl ether. The smoke level is reduced from 70HSU to 29HSU, the particulate matter is reduced from 2.801 g/h to 1.512 g/h and the smoke conversion efficiency is found out as 58.57% at full load. A slight decrease in fuel consumption and about 1 to 2% increase in brake thermal efficiency was found out from the experiment conducted, for various loads and speeds which shows obviously an improvement in the performance. The other two additives also shows the same trend except that these values slightly differ indicating that Di-Bu ether comes as second good additive and Diethylene glycol mono Bu ether as third good additive. Detailed results are reported in the results and discussions chapter and conclusions at the end. This study involved multiple reactions and reactants, such as 2-(2-(Hexyloxy)ethoxy)ethanol (cas: 112-59-4Related Products of 112-59-4).

2-(2-(Hexyloxy)ethoxy)ethanol (cas: 112-59-4) belongs to ethers. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Related Products of 112-59-4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Immunoprognostic model of lung adenocarcinoma and screening of sensitive drugs was written by Liang, Pengchen;Li, Jin;Chen, Jianguo;Lu, Junyan;Hao, Zezhou;Shi, Junfeng;Chang, Qing;Zeng, Zeng. And the article was included in Scientific Reports in 2022.Computed Properties of C13H12O2 The following contents are mentioned in the article:

Screening of mRNAs and lncRNAs associated with prognosis and immunity of lung adenocarcinoma (LUAD) and used to construct a prognostic risk scoring model (PRS-model) for LUAD. To analyze the differences in tumor immune microenvironment between distinct risk groups of LUAD based on the model classification. The CMap database was also used to screen potential therapeutic compounds for LUAD based on the differential genes between distinct risk groups. he data from the Cancer Genome Atlas (TCGA) database. We divided the transcriptome data into a mRNA subset and a lncRNA subset, and use multiple methods to extract mRNAs and lncRNAs associated with immunity and prognosis. We further integrated the mRNA and lncRNA subsets and the corresponding clin. information, randomly divided them into training and test set according to the ratio of 5:5. Then, we performed the Cox risk proportional anal. and cross-validation on the training set to construct a LUAD risk scoring model. Based on the risk scoring model, patients were divided into distinct risk group. Moreover, we evaluate the prognostic performance of the model from the aspects of Area Under Curve (AUC) anal., survival difference anal., and independent prognostic anal. We analyzed the differences in the expression of immune cells between the distinct risk groups, and also discuss the connection between immune cells and patient survival. Finally, we screened the potential therapeutic compounds of LUAD in the Connectivity Map (CMap) database based on differential gene expression profiles, and verified the compound activity by cytostatic assays. We extracted 26 mRNAs and 74 lncRNAs related to prognosis and immunity by using different screening methods. Two mRNAs (i.e., KLRC3 and RAET1E) and two lncRNAs (i.e., AL590226.1 and LINC00941) and their risk coefficients were finally used to construct the PRS-model. The risk score positions of the training and test set were 1.01056590 and 1.00925190, resp. The expression of mRNAs involved in model construction differed significantly between the distinct risk population. The one-year ROC areas on the training and test sets were 0.735 and 0.681. There was a significant difference in the survival rate of the two groups of patients. The PRS-model had independent predictive capabilities in both training and test sets. Among them, in the group with low expression of M1 macrophages and resting NK cells, LUAD patients survived longer. In contrast, the monocyte expression up-regulated group survived longer. In the CMap drug screening, three LUAD therapeutic compounds, such as resveratrol, methotrexate, and phenoxybenzamine, scored the highest. In addition, these compounds had significant inhibitory effects on the LUAD A549 cell lines. The LUAD risk score model constructed using the expression of KLRC3, RAET1E, AL590226.1, LINC00941 and their risk coefficients had a good independent prognostic power. The optimal LUAD therapeutic compounds screened in the CMap database: resveratrol, methotrexate and phenoxybenzamine, all showed significant inhibitory effects on LUAD A549 cell lines. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2Computed Properties of C13H12O2).

4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Computed Properties of C13H12O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Immunoprognostic model of lung adenocarcinoma and screening of sensitive drugs was written by Liang, Pengchen;Li, Jin;Chen, Jianguo;Lu, Junyan;Hao, Zezhou;Shi, Junfeng;Chang, Qing;Zeng, Zeng. And the article was included in Scientific Reports in 2022.Safety of 4-Benzyloxyphenol The following contents are mentioned in the article:

Screening of mRNAs and lncRNAs associated with prognosis and immunity of lung adenocarcinoma (LUAD) and used to construct a prognostic risk scoring model (PRS-model) for LUAD. To analyze the differences in tumor immune microenvironment between distinct risk groups of LUAD based on the model classification. The CMap database was also used to screen potential therapeutic compounds for LUAD based on the differential genes between distinct risk groups. he data from the Cancer Genome Atlas (TCGA) database. We divided the transcriptome data into a mRNA subset and a lncRNA subset, and use multiple methods to extract mRNAs and lncRNAs associated with immunity and prognosis. We further integrated the mRNA and lncRNA subsets and the corresponding clin. information, randomly divided them into training and test set according to the ratio of 5:5. Then, we performed the Cox risk proportional anal. and cross-validation on the training set to construct a LUAD risk scoring model. Based on the risk scoring model, patients were divided into distinct risk group. Moreover, we evaluate the prognostic performance of the model from the aspects of Area Under Curve (AUC) anal., survival difference anal., and independent prognostic anal. We analyzed the differences in the expression of immune cells between the distinct risk groups, and also discuss the connection between immune cells and patient survival. Finally, we screened the potential therapeutic compounds of LUAD in the Connectivity Map (CMap) database based on differential gene expression profiles, and verified the compound activity by cytostatic assays. We extracted 26 mRNAs and 74 lncRNAs related to prognosis and immunity by using different screening methods. Two mRNAs (i.e., KLRC3 and RAET1E) and two lncRNAs (i.e., AL590226.1 and LINC00941) and their risk coefficients were finally used to construct the PRS-model. The risk score positions of the training and test set were 1.01056590 and 1.00925190, resp. The expression of mRNAs involved in model construction differed significantly between the distinct risk population. The one-year ROC areas on the training and test sets were 0.735 and 0.681. There was a significant difference in the survival rate of the two groups of patients. The PRS-model had independent predictive capabilities in both training and test sets. Among them, in the group with low expression of M1 macrophages and resting NK cells, LUAD patients survived longer. In contrast, the monocyte expression up-regulated group survived longer. In the CMap drug screening, three LUAD therapeutic compounds, such as resveratrol, methotrexate, and phenoxybenzamine, scored the highest. In addition, these compounds had significant inhibitory effects on the LUAD A549 cell lines. The LUAD risk score model constructed using the expression of KLRC3, RAET1E, AL590226.1, LINC00941 and their risk coefficients had a good independent prognostic power. The optimal LUAD therapeutic compounds screened in the CMap database: resveratrol, methotrexate and phenoxybenzamine, all showed significant inhibitory effects on LUAD A549 cell lines. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2Safety of 4-Benzyloxyphenol).

4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Safety of 4-Benzyloxyphenol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Structural effects of morpholine replacement in ZSTK474 on Class I PI3K isoform inhibition: Development of novel MEK/PI3K bifunctional inhibitors was written by Van Dort, Marcian E.;Jang, Yongsoon;Bonham, Christopher A.;Heist, Kevin;Palagama, Dilrukshika S. W.;McDonald, Lucas;Zhang, Edward Z.;Chenevert, Thomas L.;Luker, Gary D.;Ross, Brian D.. And the article was included in European Journal of Medicinal Chemistry in 2022.Computed Properties of C3H9NO The following contents are mentioned in the article:

Established roles for PI3K and MAPK signaling pathways in tumorigenesis has prompted extensive research towards the discovery of small-mol. inhibitors as cancer therapeutics. However, significant compensatory regulation exists between these two signaling cascades, leading to redundancy among survival pathways. Consequently, initial clin. trials aimed at either PI3K or MEK inhibition alone have proven ineffective and highlight the need for development of targeted and innovative therapeutic combination strategies. We designed a series of PI3K inhibitor derivatives wherein a single morpholine group of the PI3K inhibitor ZSTK474 was substituted with a variety of 2-aminoethyl functional groups. Analogs with pendant hydroxyl or methoxy groups maintained low nanomolar inhibition towards PI3Kα, PI3Kγ, and PI3Kδ isoforms in contrast to those with pendant amino groups which were significantly less inhibitory. Synthesis of prototype PI3K/MEK bifunctional inhibitors (N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide, N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide) was guided by the structure-activity data, where a MEK-targeting inhibitor was tethered directly via a short PEG linker to the triazine core of the PI3K inhibitor analogs. These compounds (N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide, N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide) displayed nanomolar inhibition towards PI3Kα, δ, and MEK (IC₅₀ ∼105-350 nM), and low micromolar inhibition for PI3Kβ and PI3Kγ (IC₅₀ ∼1.5-3.9 μM) in enzymic inhibition assays. Cell viability assays demonstrated superior anti-proliferative activity for N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide over N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide in three tumor-derived cell lines (A375, D54, SET-2), which correlated with inhibition of downstream AKT and ERK1/2 phosphorylation. Compounds N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide and N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide also demonstrated in vivo tolerability with therapeutic efficacy through reduction of kinase activation and amelioration of disease phenotypes in the JAK2V617F mutant myelofibrosis mouse cancer model. Taken together, these results support further structure optimization of N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide and N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide as promising leads for combination therapy in human cancer as a new class of PI3K/MEK bifunctional inhibitors. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Computed Properties of C3H9NO).

2-Methoxyethylamine (cas: 109-85-3) belongs to ethers. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Computed Properties of C3H9NO

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Diethylaminoalkylamino derivatives of carbocyclic series was written by Wojahn, Hans;Erdelmeier, Karl. And the article was included in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 1942.Synthetic Route of C10H15NO The following contents are mentioned in the article:

Et₂NCH₂Ac (7 g.) and 5.5 g. m-H₂NC₆H₄OH (I) in 10 cc. EtOH, heated on the water bath for 10 min. and the solution catalytically reduced, give 3 g. of m-hydroxy-[N-(2-diethylamino-1-methylethyl)amino]benzene (II), b₁₆ 185-90°; di-HCl salt, m. 193-4°. I (5.5 g.) and 7.5 g. Et₂N(CH₂)₃Cl, refluxed in 50 cc. C₆H₆ for 12 h., give 6 g. of the N-(3-diethylaminopropyl) isomer of II, b₁₆ 185°; dipicrolonate, m. 214-15°. Et₂NCH₂CMe₂CHO gives the N-(3-diethylamino-2,2-dimethylpropyl) homolog, b₁₄ 180-5°; dipicrolonate, m. 234° (decomposition). 5-Diethylamino-2-pentanone (5.5 g.) and 3.5 g. of I yield 2 g. of the N-[4-diethylamino-1-methylbutyl] homolog of II, b₁₆ 175-8°; dipicrolonate, m. 226°. o-HOC₆H₄CHO and Et₂NCH₂CH₂NH₂, heated 10 min. on the water bath and the Schiff base catalytically reduced, give a poor yield of o-hydroxy-N-(2-diethylaminoethyl)benzylamine (III), b₁₅ 181°; dipicrate, m. 196-7° (decomposition); dipicrolonate, m. 211-12°; the m-HO isomer of III, b₁₄ 184-6°; dipicrolonate, m. 197-9°; the p-HO isomer, b₁₃ 180-2°; dipicrolonate, m. 209°; N-(3-diethylaminopropyl) homolog (IV) of III, b₁₄ 184-7° (3-g. yield from 3.5 g. of o-HOC₆H₄CHO); the m-HO isomer of IV, b₁₆ 200-3°; dipicrolonate, m. 213-15°. o-MeOC₆H₄CH₂NH₂ (5.5 g.) and 5.4 g. of Et₂NCH₂CH₂Cl in 20 cc. EtOH containing 5.5 g. AcONa, refluxed 8 h., give 5 g. of o-methoxy-N-(2-diethylaminoethyl)benzylamine (V), b₁₄ 204-6°; dipicrolonate, yellow, m. 205-7°; p-MeO isomer, b₁₈ 203-5°; dipicrate, m. 140-1°. o-EtO homolog of V, b₁₄ 205-7°; dipicrate, m. 154°. o-MeOC₆H₄CHO and Et₂N(CH₂)₃NH₂ give o-methoxy-N-(3-diethylaminopropyl)benzylamine (VI), b₁₆ 177°; dipicrolonate, m. 212-14°; m-MeO isomer, b₁₃ 191°; dipicrolonate, m. 210-11°; p-MeO isomer, b₁₆ 170°; dipicrolonate, m. 206°; o-EtO homolog of VI, b₁₄ 177°; dipicrolonate, m. 212-14°. o-Methoxy-N-(3-diethylamino-2,2-dimethylpropyl)benzylamine (VII), b₁₄ 186°; dipicrolonate, m. 208-10°; m-MeO isomer, b₁₃ 186°; dipicrolonate, m. 204°; p-MeO isomer, b₁₄ 205°; dipicrolonate, m. 217°. o-EtO homolog of VII, b₁₄ 203-4°; dipicrolonate, m. 202°. o-Methoxy-N-(4-diethylamino-1-methylbutyl)benzylamine, b₁₄ 190-4°; dipicrolonate, m. 149°; m-MeO isomer, b₁₅ 207-13°; dipicrolonate, m. 149°; p-MeO isomer, b₁₄ 203-8°; dipicrolonate, m. 204°. o-MeOC₆H₄CHO, 15 g. MeNH₂.HCl, 15 g. HCO₂Na and 20 g. anhydrous HCO₂H, heated at 150° for 3-4 h., give 13 g. of the formyl derivative, b₁₄ 180-5°; refluxing with 20% HCl for 4 h. gives 8 g. of N-methyl-o-methoxybenzylamine (VIII), b. 226°; picrolonate, m. 176°; p-MeO isomer, b. 238°; formyl derivative, b. 317°. N-Ethyl-o-methoxybenzylamine (IX), b. 238°; formyl derivative, b₁₄ 185-90°; picrolonate, m. 186-80°; m-MeO isomer, b. 245°; formyl derivative, b₁₄ 185-90°; picrolonate, m. 190°; p-MeO isomer, b. 244°; formyl derivative, b₁₄ 187-90°; picrolonate, m. 210°. VIII (3.1 g.), heated with 2.8 g. Et₂NCH₂CH₂Cl and 2.8 g. AcONa in 20 cc. AcOH for 8 h. on the water bath, gives 50% of N-methyl-N-(2-diethylaminoethyl)-o-methoxybenzylamine (X), b₁₄ 170-5°; dipicrolonate, m. 166°; p-MeO isomer, b₁₄ 172-7°; dipicrolonate, m. 195°. N-Et homolog of X, prepared from IX, b₁₄ 185-90°; dipicrolonate, m. 187°; m-MeO isomer, b₁₆ 180-5°; dipicrolonate, m. 200°; p-MeO isomer, b₁₄ 175-80°; dipicrolonate, m. 195°. VIII and Et₂N(CH₂)₃Cl give N-methyl-N-(3-diethylaminopropyl)-o-methoxybenzylamine (XI), b₁₆ 175-80°; dipicrolonate, m. 177°; p-MeO isomer, b₁₄ 195-200°; dipicrolonate, m. 190°. IX gives the N-Et homolog of XI, b₁₄ 187-9°; dipicrolonate, m. 170°; p-MeO isomer, b₁₄ 185-90°; dipicrolonate, m. 210°. This study involved multiple reactions and reactants, such as N-(3-Methoxybenzyl)ethanamine (cas: 140715-61-3Synthetic Route of C10H15NO).

N-(3-Methoxybenzyl)ethanamine (cas: 140715-61-3) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Synthetic Route of C10H15NO

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The enzymatic oxidative deamination and effect on cat behavior of mescaline and structurally-related β-phenethylamines was written by Clark, L. C. Jr.;Benington, F.;Morin, R. D.. And the article was included in Alabama J. Med. Sci. in 1964.Synthetic Route of C10H16ClNO2 The following contents are mentioned in the article:

The dosage used for all the β-phenethylamines was 25 mg./kg.; injections were intramuscularly into the cat. When rapid deamination of the β-phenethylamines was prevented by pretreating the cat with monoamine oxidase (MAO) inhibitors, the rage response of the phenethylamine was usually intensified. Some compounds, e.g., 4-methoxy-β-phenethylamine (I), that were nearly inactive prior to MAO blockade had powerful rage-producing effects after blockade. The β-phenethylamines that caused a pos. rage response also caused hyperthermia, and the degree of hyperthermia was apparently correlated with the intensity of rage. Pretreatment with MAO inhibitors greatly enhanced the pyretogenic activity of weakly active compounds E.g., I caused a rise of >8°F. after 5 mg. pheniprazine/kg. The activity of nondeaminated amines, e.g., 2,6-dimethoxy-β-phenethylamine, was not affected by pheniprazine. The pyretogenic effects did not occur in pentobarbital-anesthetized cats or in cats treated with curarelike drugs. The phenethylamines were deaminated by incubating them with semicarbazide (or other amine oxidase inhibitors used) in phosphate buffer at pH 7.4. Incubation was stopped with 5% Cl₃CCO₂H in 0.1 N HCl. Compounds Containing 2,6-dimethoxy groups or having >3 MeO groups interfere with or block deamination. None of the nondeaminated compounds interferes with the deamination of tyramine (II) or mescaline (III). Preliminary studies indicate that the deamination systems, as to which substrate can be metabolized, are similar in cat, dog, turtle, and man. Human brain rapidly metabolized phenethylamine, II, 2-methoxyphen-etheylamine, and 2,3-dimethoxy-β-phenethylamine and slowly deaminated several other III analogs, but not III. The deamination rate was dependent on the O tension, indicating that some of the physiol. effects of tissue anoxia result from the “unwanted” amines being uncatabolized and participating in neurophysiol. systems. Deamination was completely arrested by adding glucose and glucose oxidase to the enzyme substrate mixture Apparently, the deamination enzymes in rabbit liver do not contain Cu, since Cu-chelating compounds had little effect on deamination. None of the β-phenethylamines which were not deaminated inhibited II and (or) III oxidase, indicating that these structures cannot enter the specific deamination site. A structural analog of III capable of acting as a III antagonist is probably unlikely. Criteria given for deciding which structural analogs of III may be tested in the human are: the analog is deaminated by rabbit liver but not by cat or human liver; the deamination by rabbit liver is inhibited by semicarbazide but not by MO-911 (mescaline oxidase); and the analog is not a powerful excitant or pyretogenic. Only 6 compounds fulfilling these criteria were found: the 3,4,5-substituted phenethylamines having MeO, Me, EtO, or OH groups, and 3,4,5-trimethoxy-γ-phenylpropylamine. Three new substituted β-phenethylamines and one intermediate were synthesized. 2,6-Dimethoxybenzoic acid (54.6 g.) was refluxed with 17 g. LiAlH₄ in C₆H₆ for 4 hrs. and the mixture kept overnight to give 2,6-dimethoxyloxybenzyl alc., which was treated with 3.6 ml. pyridine and 49 ml. SOCl₂ under ice cooling and the mixture stirred at room temperature to yield 2,6-dimethoxybenzyl chloride. The acid chloride in acetone was stirred with 39 g. KCN in 300 ml. H₂O at room temperature for 20 hrs. to yield 41% 2,6-dimethoxyphenylacetonitrile, m. 94-5°. The nitrile (21.7 g.) was autoclaved in MeOH containing 19 g. NH₃ and 10 ml. Raney Ni catalyst. The vessel was charged with H to 1050 psig. and heated for about 1.5 hrs. at 100-20° to yield 2,6-dimethoxy-β-phenethylamine (IV), b₂₈ 165-71°, m. 56-9°; HCl salt m. 214-15°. Propylbenzene (200 g.), 30 g. paraformaldehyde, and 20 g. ZnCl₂ were treated with dry HCl gas for 4 hrs. at 60° to yield 50% 4-propylbenzyl chloride, which (84 g.) in 120 ml. EtOH was added to 32.5 g. NaCN and 37 ml. H₂O and refluxed for 4 hrs. to yield 76% 4-propylphenylacetonitrile, b_7.5 137-9°. The nitrile (60 g.) was added dropwise to an ice-cooled mixture of 20 g. LiAlH₄ in 500 ml. Et₂O and refluxed 1 hr. to give 4-propyl-β-phenethylamine-HCl, m. 190-1°. 2,4,5-Trimethylacetophenone (66 g.), 53 g. morpholine, and 19.5 g. S was refluxed 10 hrs. to yield 60% 2,4,5-trimethylphenylacetothiomorpholide, m. 110-11°. The morpholide (75 g.) was added to 165 ml. AcOH, 24 ml. concentrated H₂SO₄, and 37 ml. H₂O and refluxed 5 hrs. to yield 60% 2,4,5-trimethylphenylacetic acid, m. 128-9°. The acid (30 g.) and 35.4 g. PCl₅ was warmed for 10 min., POCl₃ removed, and the crude product poured in concentrated NH₄OH to yield 90% 2,4,5-trimethylphenylacetamide, m. 183-3.5°, which was reduced with LiAlH₄ to yield 85% 2,4,5-trimethyl-β-phenethylamine-HCl, m. 224-5°. 55 references. This study involved multiple reactions and reactants, such as 1-(2,6-Dimethoxyphenyl)ethanamine hydrochloride (cas: 1087707-43-4Synthetic Route of C10H16ClNO2).

1-(2,6-Dimethoxyphenyl)ethanamine hydrochloride (cas: 1087707-43-4) belongs to ethers. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Synthetic Route of C10H16ClNO2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reactions with halogen-substituted xanthones. II was written by Mustafa, Ahmed;Asker, Wafia;Sobhy, Mohamed Ezz El-Din. And the article was included in Journal of the American Chemical Society in 1955.Product Details of 100927-02-4 The following contents are mentioned in the article:

The reduction of halogen-substituted xanthones with LiAlH₄ and with metallic Na and EtOH led to the formation of xanthene (I) with loss of the halogen. The reduction of xanthone (II) to I with LiAlH₄ is discussed. 1-Chloro-(III), 1-6-dichloro-4-methylxanthone (IV), and 1-chloro-4-methylthiaxanthone (V) condense with aromatic thiols in the presence of KOH to yield the corresponding arylmercapto derivatives which are oxidized readily to the corresponding sulfone derivatives Whereas 2-chloroxanthone (VI) undergoes a photochem. addition reaction with I in sunlight to give the carbinol VII, the 4-isomer (VIII) of VI effects the photochem. dehydrogenation of I to 9,9′-bixanthene (IX). 2-Chloro-9-phenylxanthone (X) undergoes a photochem. oxidation in sunlight in the presence of O, yielding the peroxide (XI) of X. VI (1 g.) in 30 cc. C₆H₆ added in portions to 0.7 g. LiAlH₄ in 50 cc. Et₂O, the mixture refluxed 3 h., kept at room temperature overnight, and treated with cold dilute HCl, the Et₂O layer worked up, and the solid residue washed with about 40 cc. petr. ether and recrystallized from MeOH gave almost quant. I. The 4-isomer (XII) and the 2-Br (XIII) and 4-Br (XIV) analogs of VI gave identical results. III (1 g.) treated with LiAlH₄ in the usual manner, the mixture refluxed 2 h., decomposed with about 100 cc. cold saturated aqueous NH₄Cl, and extracted with Et₂O, the extract dried and evaporated, and the solid residue recrystallized from C₆H₆ and light petr. yielded about 0.73 g. 1-chloro-4-methylxanthydrol, colorless crystals, m. 170° (yellow melt). VI, XII, XIII, and XIV (1 g. each) in 25 cc. hot absolute EtOH added dropwise to 1 g. molten metallic Na by the method of Heller and Kostanecki (C.A. 2, 2243), the mixture steam distilled, and the resulting solid recrystallized from MeOH gave an almost quant. yield of I, m. 101°, in each case. III, IV, V (2 g. each) and 1.5 g. of the appropriate thiol in 25 cc. AmOH treated with 0.1 g. solid KOH, the mixture refluxed 3 h., held at room temperature overnight, and filtered, the filter residue washed with cold EtOH, H₂O, and cold Me₂CO, and extracted with about 60 cc. ligroine (b. 60-80°), and the residue crystallized from glacial AcOH gave the corresponding 1-arylmercapto-4-methylxanthones and -thiaxanthones. In this manner were obtained the following compounds (m.p. and % yield given): 1-(o-tolylmercapto)4-methylxanthones (XV), 170°, 52; the m-isomer, 163°, 58; the p-isomer of XV, 166°, 73; 1-phenylmercapto-6-chloro-4-methylxanthone (XVI), 164°, 81; the o-Me derivative of XVI, 205°, 62; m-Me derivative of XVI, 140°, 58; p-Me derivative of XVI, 180°, 78; 1-phenylmercapto-4-methylthiaxanthone (XVII), 150°, 83°; o-Me derivative of XVII, 162°, 64; m-Me derivative of XVII, 140°, 61; p-Me derivative of XVII, 164°, 84; all compounds formed yellow crystals and gave an orange-red color with H₂SO₄. The appropriate arylmercapto-4-methylxanthone or -thiaxanthone (1 g.) in 25 cc. glacial AcOH treated with 5 cc. 30% H₂O₂, the mixture heated 1 h. on the steam bath and held at room temperature overnight, and the resulting crystallized deposit recrystallized from glacial AcOH gave the corresponding sulfones (mercapto compound used, m.p., and % yield given): XV, 260°, 63; m-isomer of XV, 226°, 61; p-isomer of XV, 270°, 76; XVI, 210-12°, 84; o-Me derivative of XVI, 242°, 73; m-Me derivative of XVI, 198°, 69; p-Me derivative of XVI, 240°, 79; XVII, 176°, 82; o-Me derivative of XVII, 180°, 75; m-Me derivative of XVII, 182°, 70; p-Me derivative of XVIII, 210°, 85. I (1 g.) and 1.3 g. VI in 30 cc. C₆H₆ exposed 10 days (May) to sunlight and the resulting colorless needles washed with about 10 cc. C₆H₆ and recrystallized from hot C₆H₆ yielded about 80% VII, m. 174°; it dissolved with difficulty with an orange color in concentrated H₂SO₄. VIII (0.7 g.) and 0.5 g. I in 25 cc. C₆H₆ exposed 10 days (July) to sunlight, the C₆H₆ removed in vacuo, the oily residue cooled, and the semisolid mass washed with about 25 cc. petr. ether (b. 50-60°) and recrystallized from C₆H₆ yielded about 0.32 g. IX, m. 201°. The Grignard solution from 0.9 g. Mg and 9 g. PhBr in 50 cc. dry Et₂O treated with 1 g. VI in 50 cc. dry C₅H₆, the Et₂O evaporated, the residual mixture heated 1 h. on the steam bath, kept at 25° overnight, and poured slowly into 100 cc. saturated aqueous NH₄Cl, the Et₂O layer dried, filtered, and evaporated, the oily residue washed with about 35 cc. petr. ether below 40°, and the resulting solid crystallized from ligroine gave about 0.87 g. 2-chloro-9-phenylxanthydrol, m. 113°; it gave an orange color with H₂SO₄; it gave reduced with Zn dust and AcOH almost 100% X, colorless crystals, m. 139° (from EtOH). X (1 g.) in solution exposed 15 days (Apr.) to sunlight gave about 0.63 g. XI, m. 221° (decomposition) (brown-red melt); it gave an orange-yellow color with H₂SO₄. XI (0.5 g.) heated 0.5 h. at 270° yielded 0.18 g. xanthone. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Product Details of 100927-02-4).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Product Details of 100927-02-4

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Clark, N. G.; Cranham, J. E.; Greenwood, D.; Marshall, J. R.; Stevenson, H. A. published an article in 1957, the title of the article was Toxicity of organic sulfides to the eggs and larvae of the glasshouse red spider mite. III. Benzyl phenyl sulfides substituted only by halogens.Synthetic Route of 53136-21-3 And the article contains the following content:

Nuclear halogenation had a strong effect on the biol. activity of benzyl Ph sulfide, which was virtually inactive. In monosubstituted compounds, substitution in the para position of the Ph moiety gave products much less active than the corresponding compounds substituted in the para position of the benzyl moiety. With substituted Ph compounds there was a general rise in activity from F through Cl and Br to I. With few exceptions, all compounds substituted by halogen in the para position of both nuclei or in the benzyl moiety only were of high activity. Position of substitution played a role in activity, ortho-substituted benzyl derivatives being relatively less active. Substitution by more than 1 halogen atom in either nucleus resulted in compounds of lower activity than the corresponding compounds substituted only in the para positions. The following newly synthesized compounds were among those evaluated: XC6H4CH2SC6H4Y (X, Y, and m.p. (or b.p.) given): H, p-F, 32.5-33°; H, I, 52-3°; H, 2,4,-5-Cl3, 118-19°; H, 2,5-Cl2, 65°; H, p-Br, 64-5°; H, p-I, 77°; p-F, H, 62-2.5°; p-F, p-F, 44.5-5.5°; p-F, I, 49-50°; p-F, p-Br, 56.5-7.5°; p-F, p-I, 75°; ο-Cl, p-F, b1.5, 141-3°; ο-Cl, I, b2.0 170°, m. 32°; m-Cl, p-F, b2.0 158-60°; m-Cl, I, b2.0 172-5°; I, H, 78°; I, p-F, 34.5-5.5°; I, I, 72°; I, 2,5-Cl2, 113-14°; I, 2,4,5-Cl3, 76-7°; I, p-Br, 87-8°; I, p-I, 102°; 2,4-Cl2, H, b1.5 163-5°; 2,4-Cl2, p-F, 167°; 2,4-Cl2, I, 58-9°; 2,6-Cl2, H, 39-40°; 2,6-Cl2, p-F, 51°; 2,6-Cl2, I, 69-70°; p-Br, H, 78°; p-Br, p-F, 44-5°; p-Br, I, 83-4°; p-Br, p-Br, 101°; p-Br, p-I, 116°; p-I, H, 88°; p-I, p-F, 56°; p-I, I, 101°; p-I, p-Br, 118°; and p-I, p-I, 131°. XC6H4CH2SOnC6H4Y (X, Y, n, and m.p. given): H, p-F, 1, 138-40°; H, p-F, 2, 153.5-4.5°; H, I, 1, 134°; H, I, 2, 144-5°; H, p-Br, 1, 141-2°; H, p-Br, 2, 158-9°; H. p-I, 1, 128°; H, p-I, 2, 182°; p-F, p-F, 1, 160-1°; p-F, p-F, 2, 186-7°; p-F, I, 2, 156-7°; p-F, p-Br, 2, 171.5-72°; p-F, p-I, 1, 171°; p-F, p-I, 2, 201°; o-Cl, p-F, 2, 107-8°; o-Cl, I, 1, 73-4°; o-Cl, I, 2, 120-1°; m-Cl, p-F, 1, 82.5-3.5°; m-Cl, p-F, 2, 135-6°; m-Cl, I, 1, 94-6°; m-Cl, p-Cl, 2, 125° and 130°; I, H, 1, 173°; I, H, 2, 190°; I, p-F, 1, 125-6°; I, p-F, 2, 144-5°; I, I, 1, 124°; I, I, 2, 150°; I, p-Br, 1, 132-3°; I, p-Br, 2, 169-70°; I, p-I, 1, 159°; I, p-I, 2, 194°; p-Br, H, 1, 179°; p-Br, H, 2, 192-3°; p-Br, p-F, 1, 141°; p-Br, p-F, 2, 160-1°; p-Br, I, 1, 135-6°; p-Br, I, 2, 158-9°; p-Br, p-Br, 1, 145-6°; p-Br, p-Br, 2, 179-80°; p-Br, p-I, 1, 180°; p-Br, p-I, 2, 213°; p-I, H, 1, 191°; p-I, H, 2, 209°; p-I, p-F, 1, 171°; p-I, p-F, 2, 196°; p-I, I, 1, 153°; p-I, I, 2, 187°; p-I, p-Br, 1, 171°; p-I, p-Br, 2, 202°; p-I, p-I, 1, 197°; and p-I, p-I, 2, 239°. The experimental process involved the reaction of Benzyl(4-bromophenyl)sulfane(cas: 53136-21-3).Synthetic Route of 53136-21-3

Benzyl(4-bromophenyl)sulfane(cas:53136-21-3) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Synthetic Route of 53136-21-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Griffith, R. H.; Hope, Edward published an article in 1925, the title of the article was Synthesis of 5,5′-dibromo-6,6′-dimethoxy-2,2′-bisoxythionaphthene.HPLC of Formula: 152626-77-2 And the article contains the following content:

5-Bromo-2-acetylamino-p-tolyl Me ether (I), m. 191°; hydrolysis with concentrated HCl gives the amine, m. 100° (Bz derivative, m. 159°); the azo dye with β-C10H7OH, red needles with green luster, m. 210°. Diazotized and reduced with SnCl4, the amine gives a hydrazine, pale brown, m. 192°, which, on treatment with CuSO4 and oxidation with alk. KMnO4, yields 3-bromoanisic acid, m. 217-8°. Since the 2-Br derivative is recorded as m. 212°, it was synthesized from 2-bromo-p-tolyl Me ether, b16 114° b760 222°, and found to m. 199°. Oxidation of I with KMnO4 in the presence of MgSO4 gives about 70% of 5-bromo-2-acetylamino-4-methoxybenzoic acid, m. 253°; hydrolysis with concentrated HCl gives 4-bromo-m-anisidine, m. 90.5° (Bz derivative m. 124°); hydrolysis with alkali gives 5-bromo-2-amino-4-methoxy-benzoic acid, pale brown, m. 201°, decomposed 213° (Na salt, long needles; Cu salt, green). Diazotized, treated with Na2S2 and boiled with Zn dust in Na2CO3 solution, it yields 5-bromo-4-methoxy-2-thiolbenzoic acid, which, because of its ease of oxidation, is used as the Na salt in the condensation with ClCH2CO2H, forming 4-bromo-2-carboxy-5-methoxy-phenylthiolacetic acid (II), pale brown, m. 243° (decomposition). Heated with AcONa and Ac2O, dissolved in 3% alkali and treated with K3Fe(CN)6, it gives 5,5′-dibromo-6,6′-dimethoxy-2,2′-bisoxythionaphthene (III), dark red, m. 355-60°; the dye is reprecipitated from its deep blue solution in concentrated H2SO4 in a gelatinous state very suitable for the preparation of the vat, which is pale yellow and dyes cloth a good scarlet. The PhNO2 solution shows an absorption band with a maximum at λ = 529; “Helindone Fast Scarlet R” shows a similar band with a maximum at λ = 520. II and isatin give the compound C17H10O3N-BrS (IV), which has a much bluer shade than III; its H2SO4 solution is purple but its dyeing properties are unsatisfactory, probably on account of further reaction during reduction. II and acenaphthenequinone give an orange powder (V), m. 337°, giving dark brown solutions in concentrated H2SO4 and dyeing cloth a good orange from a bright blue bath. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).HPLC of Formula: 152626-77-2

4-Bromo-5-methoxy-2-methylaniline(cas:152626-77-2) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. HPLC of Formula: 152626-77-2

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Ether – Wikipedia,
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Holt, H. S.; Reid, E. E. published an article in 1924, the title of the article was Effect of sulfur on the color of triphenylmethane dyes.Name: Benzyl(4-bromophenyl)sulfane And the article contains the following content:

S in the p-position has a decided auxochrome effect on the color and the shift is towards the blue. S in the o-position has a similar effect but _to a less degree. Increasing the mol. weight of the alkyl groups results in a loss of some of the auxochrome effect. In general the auxochrome effect of the various groups is in the order SMe, OMe, Me. The following thioethers were made from the NH2 derivative through the Sandmeyer reaction (% yields in parentheses): o-bromophenyl isopropyl sulfide, b11 130-5°, d2525 1.2804 (35); Ph derivative, b12 175-7°, d2525 1.3733 (50); p-bromophenyl Me sulfide, m. 27° (55); iso-Pr derivative, b11 120°, d2525 1.2338 (60); iso-Bu derivative, b15, 140-3°, d2525 1.1467 (37); benzyl derivative, m. 48° (50); p-bromophenyl Me sulfone, m. 97.5° (50). These Br derivatives were then changed into the Grignard reagent and reacted with Michler’s ketone; dyes could not be prepared containing the Ph and benzyl sulfide or Me sulfone groups, because the Grignard reaction did not take place with these derivatives The following colors were produced on wool by the substituted malachite greens thus obtained (1st color, o-derivative; 2nd, p-): unsubstituted, yellowish green; Me, dull bluish green, bright yellowish green; OMe, dull yellowish green, same; SMe, bluish green (turquoise), dull reddish blue; SCHMe2,-, dull blue gray; SC5H11 (iso),-, dull yellowish green. The experimental process involved the reaction of Benzyl(4-bromophenyl)sulfane(cas: 53136-21-3).Name: Benzyl(4-bromophenyl)sulfane

Benzyl(4-bromophenyl)sulfane(cas:53136-21-3) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Name: Benzyl(4-bromophenyl)sulfane

Referemce:
Ether – Wikipedia,
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