Tag: 200-300

β(4-Hydroxy-2-methylphenoxy)lactic acid, a metabolite of mephenesin was written by Ludwig, B. J.;Luts, H.;West, W. A.. And the article was included in Journal of the American Chemical Society in 1955.Recommanded Product: 4-(Benzyloxy)-3-methylphenol The following contents are mentioned in the article:

2,1,4-MeC₆H₃(OH)₂ (I) (24.8 g.) in 8.0 g. NaOH in 100 cc. H₂O, the mixture refluxed 2 hrs. with 12.5 g. ClCH₂CH(OH)CO₂H (II), cooled, saturated with CO₂, and washed with Et₂O to recover 19.5 g. unchanged I, the aqueous layer concentrated in vacuo, acidified with HCl, and extracted with Et₂O, the extract evaporated, the residue (2.6 g.) sublimed in vacuo to remove unchanged I, and the tan-colored, solid residue (1.5 g.) recrystallized repeatedly from hot PrNO₂ gave 3,4-Me(HO)C₆H₃OCH₂CH(OH)CO₂H, slightly colored crystals, m. 121-2°. Dihydropyran (16.8 g.) added with stirring to 12.4 g. I in 100 cc. dioxane containing 2 drops concentrated HCl at 25-30°, the mixture allowed to warm to 60°, and diluted with Et₂O, the organic layer extracted with 10% aqueous NaOH, the alk. solution neutralized with CO₂, diluted with H₂O, and extracted with CCl₄, the extract evaporated, and the colored residue (5.3 g.) recrystallized from Et₂O-ligroine containing a drop dihydropyran gave 4- hydroxy-3-methylphenyl-2-tetrahydropyranyl ether (III), white crystals, m. 90-1.5°. III (4.16 g.) in 12 g. 10% aqueous NaOH refluxed 3 hrs. with 1.25 g. II, the solution cooled, saturated with CO₂, and extracted with Et₂O, the aqueous portion acidified with HCl, saturated with Na₂SO₄, and extracted with Et₂O, the extract dried and evaporated, and the colored, solid residue (0.8 g.) recrystallized twice from C₆H₆-Et₂O and once from PrNO₂ gave 410 mg. 2,4-Me(HO)C₆H₃OCH₂CH(OH)CO₂H (IV), m. 168-9°. Synthetic and natural IV were identical with regard to their m.p., ultraviolet absorption, color test with Ehrlich reagent, and chromatographic behavior on paper. III (1.04 g.) treated in the usual manner with 1 equivalent PhCH₂Cl in 1 equivalent aqueous NaOH, the intermediate mixed diether hydrolyzed, and the mixture worked up in the usual manner gave a small amount of 2,5-PhCH₂(HO)C₆H₃Me, white crystals, m. 69.5-70.5°. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Recommanded Product: 4-(Benzyloxy)-3-methylphenol).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. 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.Recommanded Product: 4-(Benzyloxy)-3-methylphenol

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

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

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

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

Design, synthesis, biological evaluation and molecular modeling of novel 1H-pyrazolo[3,4-d]pyrimidine derivatives as BRAF^V600E and VEGFR-2 dual inhibitors was written by Wang, Yuanyuan;Wan, Shanhe;Li, Zhonghuang;Fu, Yu;Wang, Guangfa;Zhang, Jiajie;Wu, Xiaoyun. And the article was included in European Journal of Medicinal Chemistry in 2018.Application of 103-16-2 The following contents are mentioned in the article:

Aiming to explore novel BRAF^V600E and VEGFR-2 dual inhibitors, a series of 1H-pyrazolo[3,4-d]pyrimidine derivatives were designed, synthesized and biol. evaluated. Most of the synthesized 1H-pyrazolo[3,4-d]pyrimidine compounds displayed moderate to high potent activity in both enzymic and cellular proliferation assays. Among these compounds, N-(4-chlorophenyl)-1-methyl-5-((1-methyl-1H-pyrazolo [3,4-d]pyrimidin-4-yl)oxy)-1H-benzo[d]imidazol-2-amine, 1-methyl-5-((1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl) oxy)-N-(p-tolyl)-1H-benzo[d]imidazol-2-amine, N-(4-bromophenyl)-1-methyl-5-((1-methyl-1H-pyrazolo [3,4-d]pyrimidin-4-yl)oxy)-1H-benzo[d]imidazol-2-amine and 1-methyl-5-((1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl) oxy)-N-(4-(trifluoromethoxy)phenyl)-1H-benzo[d]imidazol-2-amine showed remarkably high inhibitory activities against both BRAF^V600E and VEGFR-2 kinase comparable to pos. control Sorafenib. Particularly, compound 1-methyl-5-((1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl) oxy)-N-(4-(trifluoromethoxy)phenyl)-1H-benzo[d]imidazol-2-amine also showed potent anti-proliferative activity against BRAF^V600E-expressing A375 (IC₅₀ = 1.74 μM) and H-29 (IC₅₀ = 6.92 μM) as well as VEGFR-2-expressing HUVEC (IC₅₀ = 5.89 μM), which was also comparable to Sorafenib. Furthermore, kinase selectivity profile showed that 1-methyl-5-((1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl) oxy)-N-(4-(trifluoromethoxy)phenyl)-1H-benzo[d]imidazol-2-amine had almost poor or no significant inhibitory activity against wild-type BRAF and 15 other tested protein kinases. Flow cytometric anal. showed that compound 1-methyl-5-((1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl) oxy)-N-(4-(trifluoromethoxy)phenyl)-1H-benzo[d]imidazol-2-amine mainly arrested the A375 and HUVEC cell lines in the G₀/G₁ stage with a concentration-dependent effect. In addition, the mol. docking and mol. dynamics simulations suggested that 1-methyl-5-((1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl) oxy)-N-(4-(trifluoromethoxy)phenyl)-1H-benzo[d]imidazol-2-amine adopted a similar binding pattern with Sorafenib at the ATP-binding sites of BRAF^V600E and VEGFR-2. Taken together, these results indicated that compound 1-methyl-5-((1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl) oxy)-N-(4-(trifluoromethoxy)phenyl)-1H-benzo[d]imidazol-2-amine may serve as novel lead compound in research on more effective BRAF^V600E and VEGFR-2 dual inhibitors. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2Application of 103-16-2).

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. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Application of 103-16-2

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

Elbs persulfate oxidation of phenols and its adaptation to the preparation of monoalkyl ethers of quinols was written by Baker, Wilson;Brown, N. C.. And the article was included in Journal of the Chemical Society in 1948.Synthetic Route of C14H14O2 The following contents are mentioned in the article:

The oxidation of phenols to hydroquinones by K₂S₂O₈ in alk. medium is termed “Elbs K₂S₂O₈ oxidation” [cf. J. prakt. Chem. 48, 179(1893)]. The phenol (1 mol.) in 5 mols. 10% NaOH is oxidized by the slow addition (3-4 h.) of aqueous saturated K₂S₂O₈ (temperature not above 20°); after standing overnight, the solution is acidified (Congo red), extracted with ether, the aqueous layer treated with excess HCl, heated 0.5 h. on a water bath, cooled, and extracted with ether. The following give the recovered phenol and the yield of oxidation product on the basis of unrecovered phenol (%): PhOH to p-C₆H₄(OH)₂ 48, 34; ο-HOC₆H₄CHO to 2,5-(HO)₂C₆H₃CHO 24, 33; 1,3,5-Me₂C₆H₃OH to 2,6,1,4-Me₂C₆H₂(OH)₂ (I) 30, 51; 1,3,2-Me₂C₆H₃OH (II) to I 26, 40; 2,5-Me₂C₆H₃OH to 2,5,1,4-Me₂C₆H₂(OH)₂ 25, 56; ο-ClC₆H₄OH to 2,1,4-ClC₆H₃(OH)₂ 20, 62; p-MeC₆H₄OH to 3,4-(HO)₂C₆H₃Me 20, 11; vanillin to 5,3,4-MeO(HO)₂C₆H₂CHO 48, 3.6; p-HOC₆H₄CO₂H to 3,4-(HO)₂C₆H₃CO₂H 71, 2. Some of the yields can be improved by isolation of the intermediate sulfate but this involves evaporation of large volumes of solution 2,6,4-Me₂(HO)C₆H₂OSO₃K (from II) (25 g.) in 60 cc. 90% EtOH and 50 cc. H₂O containing 7 g. NaOH, treated (0.25 h.) at the b.p. with 14 g. PhCH₂Cl and refluxed an addnl. 2 h., gives 22 g. 5-(benzyloxy)-m-2-xylenol, m. 97-9°. ο-HOC₆H₄Me (21 g.) gives 27 g. of the K SO₄ salt, which with Me₂SO₄ and NaOH yields 27% 5,2-HO(MeO)C₆H₃Me; the m-isomer gives 34% 2,5-HO(MeO)C₆H₃Me. ο-HOC₆H₄Me yields 2-(benzyloxy)-5-hydroxytoluene, m. 69-70°; the 5-Me ether b_0.5 135-8° and with HCl yields 2,5-HO(MeO)C₆H₃Me. II gives 2-methoxy-m-5-xylenol, m. 83°. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Synthetic Route of C14H14O2).

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. Polyesters are important plastics, with monomers linked by ester moieties. 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. Synthetic Route of C14H14O2

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Liu, Jianchao; Xiao, Xiao; Han, Puren; Zhou, Huiwen; Yin, Qi-Shuang; Sun, Jian-Song published an article in 2020, the title of the article was Palladium-catalyzed C-glycosylation and annulation of o-alkynylanilines with 1-iodoglycals: convenient access to 3-indolyl-C-glycosides.Name: 2-((4-Methoxyphenyl)ethynyl)aniline And the article contains the following content:

An efficient and practical approach for the synthesis of 3-indolyl-C-Δ1,2-glycosides through a palladium-catalyzed annulation/C-glycosylation sequence of o-alkynylanilines with 1-iodoglycals has been developed. This methodol. has a wide scope of substrates and gives access to 3-indolyl-C-Δ1,2-glycosides in high yields. Furthermore, the product obtained here exhibits a high utility for further transformations. The experimental process involved the reaction of 2-((4-Methoxyphenyl)ethynyl)aniline(cas: 157869-15-3).Name: 2-((4-Methoxyphenyl)ethynyl)aniline

The Article related to c aryl glycoside preparation iodoglycal annulation, alkynylaniline annulation glycosylation palladium catalyzed indolylglycoside, Carbohydrates: Glycosides and other aspects.Name: 2-((4-Methoxyphenyl)ethynyl)aniline

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Ruzo, Luis O.; Unai, Tadaaki; Casida, John E. published an article in 1978, the title of the article was Decamethrin metabolism in rats.Electric Literature of 66855-92-3 And the article contains the following content:

On oral administration to male rats, the pyrethroid insecticide decamethrin (I) [52918-63-5] and various metabolites derived from its acid and alc. fragments were almost completely eliminated from the body within 2-4 days. Metabolites of the cyano substituent were eliminated more slowly, especially from the skin and stomach, due in the latter case to temporary retention of thiocyanate which was formed from released cyanide. The excreted metabolites included: esters monohydroxylated at the 2′, 4′, and 5 positions of the alc. moiety; 2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropanecarboxylic acid [59952-39-5] and its glucuronide [66855-97-8] and glycine conjugate [66855-98-9] and a hydroxylated derivative [66855-99-0] of this acid, with the hydroxymethyl group trans to the carboxyl, and its glucuronide [66856-00-6]; 3-phenoxybenzoic acid [3739-38-6] and its glucuronide [57991-35-2] and glycine conjugate [57991-36-3], 3-(4-hydroxyphenoxy)benzoic acid [35065-12-4] and its glucuronide [66856-01-7] and sulfate conjugate [58218-91-0], and 3-(2-hydroxyphenoxy)benzoic acid sulfate [61183-26-4]; thiocyanate [302-04-5] and 2-iminothiazolidine-4-carboxylic acid [2150-55-2]. Trans-Decamethrin [64363-96-8] was also rapidly metabolized in rats. The experimental process involved the reaction of 3-(2-Methoxyphenoxy)benzaldehyde(cas: 66855-92-3).Electric Literature of 66855-92-3

The Article related to decamethrin metabolism rat, Toxicology: Agrochemical and other aspects.Electric Literature of 66855-92-3

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On January 27, 2011, Schwede, Wolfgang; Klar, Ulrich; Moeller, Carsten; Rotgeri, Andrea; Bone, Wilhelm published a patent.HPLC of Formula: 53136-21-3 The title of the patent was 17-Hydroxy-17-pentafluoroethylestra-4,9(10)-dien-11-aryl derivatives as progesterone receptor antagonists and their preparation and use in the treatment of diseases. And the patent contained the following:

The invention relates to 17-hydroxy-17-pentafluoroethylestra-4,9(10)-dien-11-aryl derivatives of formula I exhibiting progesterone-antagonistic effects and to methods for the production thereof, to the use thereof for the treatment and/or prophylaxis of diseases and to the use thereof for producing medicaments for the treatment and/or prophylaxis of diseases, in particular uterine fibroids (myomas, uterine leiomyomas), endometriosis, menorrhagia, meningiomas, hormone-dependent mammary carcinomas and menopause-associated troubles, or for fertility control and emergency contraception. Compounds of formula I wherein R1 is SH and derivatives, SOH and derivatives, SO2H and derivatives, SONH2 and derivatives, (un)substituted aryl, etc.; X is O, NOH and derivatives and NNHSO2H and derivatives; and stereoisomers, salts, solvates, solvated salts, and all crystal modifications thereof, are claimed. Example compound II was prepared by addition of pentafluoroiodoethane to (5’R,8’S,10’R,14’S)-5,5,13′-trimethyl-1′,2′,6′,7′,12′,13′,14′,15′,16′-decahydro-17’H-spiro[1,3-dioxan-2,3′-[5,10]epoxycyclopenta[a]phenanthren]-17′-one, followed by conjugate addition of 1-bromo-4-methylthiobenzene in the presence of magnesium and copper, and deacetalization. All the invention compounds were evaluated for their progesterone receptor antagonistic activity. From the assay, it was determined that compound II exhibited IC50 values of 0.011 nmol/L and 0.012 nmol/L towards progesterone receptor A and B, resp. The experimental process involved the reaction of Benzyl(4-bromophenyl)sulfane(cas: 53136-21-3).HPLC of Formula: 53136-21-3

The Article related to estradiene aryl derivative preparation progesterone receptor antagonist treatment disease, Steroids: Estranes and other aspects.HPLC of Formula: 53136-21-3

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