Ethers-buliding-blocks

CYP 17 and CYP 19 Inhibitors. Evaluation of Fluorine Effects on the Inhibiting Activity of Regioselectively Fluorinated 1-(Naphthalen-2-ylmethyl)imidazoles was written by Hartmann, Rolf W.;Palusczak, Anja;Lacan, Fabrice;Ricci, Giacomo;Ruzziconi, Renzo. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2004.SDS of cas: 104197-14-0 This article mentions the following:

Regioselectively fluorinated 1-(naphth-2-ylmethyl)imidazoles 1a-h have been synthesized starting from the corresponding (naphth-2-yl)methanols (2). 2a-d have been obtained by LiAlH4-promoted reduction of fluorinated 1-methyl-2-naphthaldehydes. The latter were easily prepared in fairly good overall yields by ceric ammonium nitrate (CAN)-promoted oxidative addition of the suitable 3-(fluoroaryl)-1-trimethylsilyloxy-1-butenes to Et vinyl ether in methanol followed by cyclization of the resulting acetals in strongly acidic medium in the presence of DDQ. 2e-h were prepared by LiAlH4-promoted reduction of the corresponding fluorinated Me 2-naphthoates. The latter were more profitably obtained by reacting the suitable benzyl bromide with the sodium salt of di-Me 2-(2,2-dimethoxyethyl)malonate in DMF followed by demethoxycarbonylation and acid catalyzed cyclization of the resulting acetals. Compared with the non-fluorinated parent compounds 1i-l, fluorinated 1-(naphth-2-yl)methylimidazoles 1a-h turned out to be potent inhibitors of CYP17 and CYP19 enzymes. The most active inhibitor of CYP17 is 1c, whereas CYP19 is strongly inhibited by 1b, 1e, and 1g. Interestingly, 1g is a potent dual inhibitor also being very active towards CYP19. In the experiment, the researchers used many compounds, for example, 4-Bromo-2,6-difluoroanisole (cas: 104197-14-0SDS of cas: 104197-14-0).

4-Bromo-2,6-difluoroanisole (cas: 104197-14-0) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.SDS of cas: 104197-14-0

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

BioMOF-Mn: An Antimicrobial Agent and an Efficient Nanocatalyst for Domino One-Pot Preparation of Xanthene Derivatives was written by Ghamari kargar, Pouya;Bagherzade, Ghodsieh;Beyzaei, Hamid;Arghavani, Soheila. And the article was included in Inorganic Chemistry in 2022.Recommanded Product: (4-Methoxyphenyl)methanol This article mentions the following:

In this paper, a new Mn-based metal-organic framework [UoB-6] was obtained via a one-step ultrasonic irradiation method with the ligand (H₂bdda: 4,4′-(1,4-phenylenebis(azaneylylidene))bis(methanelylidene))dibenzoic acid. The structural integrity of the synthesized BioMOF-Mn was corroborated by FT-IR, EDX, ICP, XRD, TEM, DLS, FESEM, and BET-BJH analyses. The aerobic oxidative domino reaction of benzyl alcs. or aldehydes with dimedone derivatives was performed in the presence of the UoB-6 catalyst to produce xanthene derivatives in good yields. Hot filtration and Hg poisoning tests proved the heterogeneous nature of the catalyst. Novel synthesized xanthene-based bis-aldehydes were introduced as potent HDAC1 inhibitors according to mol. docking calculations Finally, the inhibitory activities of Mn-MOF nanoparticles were evaluated on Escherichia coli and Candida albicans. The MIC, MBC, and MFC values were determined from 2048 to 4096μg·mL^-1 according to antimicrobial susceptibility testing methods. The inhibitory effects of antimicrobial agents can be exacerbated when loaded on BioMOFs. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Recommanded Product: (4-Methoxyphenyl)methanol).

(4-Methoxyphenyl)methanol (cas: 105-13-5) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Recommanded Product: (4-Methoxyphenyl)methanol

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

Enhancement of transfection activity in HEK293 cells by lipoplexes containing cholesteryl nitrogen-pivoted aza-crown ethers was written by Sewbalas, Alisha;Ul Islam, Rafique;van Otterlo, Willem A. L.;de Koning, Charles B.;Singh, Moganavelli;Arbuthnot, Patrick;Ariatti, Mario. And the article was included in Medicinal Chemistry Research in 2013.Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Two nitrogen-pivoted aza-crown ethers (aza-CEs) linked to the cholesteryl-fused ring system N-(cholesteryloxycarbonyl)aza-15-crown-5 and N-(cholesteryloxycarbonyl)aza-18-crown-6 have been incorporated into cationic liposomes containing the cytofectin 3β[N-(N’,N’-dimethylaminopropane)carbamoyl] cholesterol (Chol-T) and the neutral co-lipid dioleoylphosphatidylethanolamine. These novel liposomes form stable complexes with plasmid DNA and afford it good protection from serum nuclease digestion. Ethidium displacement studies suggest that the DNA is more loosely packed in aza-CE containing lipoplexes, a finding which is supported by band shift assays that reveal N/P end point ratios of 2:1, 3:1 and 3.5:1 for Chol-T control liposomes, aza-15-crown-5 and aza-18-crown-6 containing liposomes, resp. The transfection activities of crown ether-containing lipoplex formulations in the human embryonic kidney cell line HEK293 are twofold greater than those achieved by Chol-T lipoplexes not containing the aza-CEs. This observation may be attributable to the more loosely packed DNA, which facilitates disassembly, and to endosomal perturbations caused by macrocycle entrapped cations. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

Design and synthesis of Tröger’s base ditopic receptors: host-guest interactions, a combined theoretical and experimental study was written by Bhaskar Reddy, Manda;Shailaja, Myadaraboina;Manjula, Alla;Premkumar, Joseph Richard;Sastry, Garikapati Narahari;Sirisha, Katukuri;Sarma, Akella Venkata Subrahmanya. And the article was included in Organic & Biomolecular Chemistry in 2015.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Two flexible Troeger base ditopic receptors C4TB and C5TB incorporating an aza-crown ether were designed and synthesized for bis[ammonium ion] complexation. A comprehensive study of host-guest interactions was established by ¹H NMR spectroscopy and DFT calculations Bis[ammonium chloride] with a short alkyl chain spacer showed the highest affinity for the receptors. M06-2X/cc-pVTZ calculations including the solvent effects on host-guest complexes were employed to explain and rationalize the exptl. trends. The short N-H···O or N-H···N hydrogen-bond distances observed in the range of 1.71-1.98 Å indicate the existence of a strong charge assisted hydrogen bonding between the host and the guest. The unusual behavior (higher binding constant) of A5 in ¹H NMR titration is traced to the conformational folding of the guest. The synthesis of the target compounds was achieved by a reaction of 1,4,7-trioxa-10-azacyclododecane and 1,4,7,10-tetraoxa-13-azacyclopentadecane with a bis(bromoethoxy)6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine derivative (Troger’s base). In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

The Coupling of Arylboronic Acids with Nitroarenes Catalyzed by Rhodium was written by Zheng, Xing-Wang;Ding, Jin-Chang;Chen, Jiu-Xi;Gao, Wen-Xiao;Liu, Miao-Chang;Wu, Hua-Yue. And the article was included in Organic Letters in 2011.SDS of cas: 54916-28-8 This article mentions the following:

The coupling of arylboronic acids with electron-deficient nitroarenes was realized for the first time by using a rhodium(I) catalyst under an air atm., achieving unsym. diaryl ethers, e.g., I with yields ranging from poor to good. From a deuterium labeling experiment, the oxygen atom is derived from ambient water. The efficiency of this reaction was demonstrated by its compatibility with fluoro, bromo, chloro, and trifluoromethyl groups. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8SDS of cas: 54916-28-8).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.SDS of cas: 54916-28-8

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

Michael acceptor approach to the design of new salvinorin A-based high affinity ligands for the kappa-opioid receptor was written by Polepally, Prabhakar R.;Huben, Krzysztof;Vardy, Eyal;Setola, Vincent;Mosier, Philip D.;Roth, Bryan L.;Zjawiony, Jordan K.. And the article was included in European Journal of Medicinal Chemistry in 2014.Synthetic Route of C11H12O4 This article mentions the following:

The neoclerodane diterpenoid salvinorin A is a major secondary metabolite isolated from the psychoactive plant Salvia divinorum. Salvinorin A has been shown to have high affinity and selectivity for the κ-opioid receptor (KOR). To study the ligand-receptor interactions that occur between salvinorin A and the KOR, a new series of salvinorin A derivatives bearing potentially reactive Michael acceptor functional groups at C-2 was synthesized and used to probe the salvinorin A binding site. The κ-, δ-, and μ-opioid receptor (KOR, DOR and MOR, resp.) binding affinities and KOR efficacies were measured for the new compounds Although none showed wash-resistant irreversible binding, most of them showed high affinity for the KOR, and some exhibited dual affinity to KOR and MOR. Mol. modeling techniques based on the recently-determined crystal structure of the KOR combined with results from mutagenesis studies, competitive binding, functional assays and structure-activity relationships, and previous salvinorin A-KOR interaction models were used to identify putative interaction modes of the new compounds with the KOR and MOR. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Synthetic Route of C11H12O4).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Synthetic Route of C11H12O4

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

Development of room-temperature electrodeposition techniques for metallic Mg and metallic Al using safe electrolytes and applications to next-generation battery and/or future plating was written by Kitada, Atsushi. And the article was included in Hyomen Gijutsu in 2020.Reference of 112-49-2 This article mentions the following:

This paper describes development of room-temperature electrodeposition techniques for metallic magnesium and metallic aluminum using safe electrolytes and applications to next-generation battery and/or future plating. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Reference of 112-49-2).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Reference of 112-49-2

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

Optimization of antroquinonol production in solid-state fermentation of Antrodia camphorata using response surface methodology was written by Lu, Ruiqiu;Hu, Yongdan;Zhang, Baobo;Xu, Ganrong. And the article was included in Shipin Kexue (Beijing, China) in 2015.Application In Synthesis of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

In this study, response surface methodol. based on Box-Behnken design was used to optimize the culture conditions for the production of the bioactive metabolite antroquinonol in solid-state fermentation of Antrodia camphorata. The optimal culture conditions were determined as inoculum amount of 296.80 mg/kg, Triton X-100 concentration of 1.10 mL/kg and coenzyme Q₀ concentration of 0.23 g/kg. Under these conditions, the maximum predicted yield of antroquinonol was 865.85 mg/kg, which was in good agreement with the exptl. value of 865.32 mg/kg. Therefore, the established model could be used for predicting the culture conditions of Antrodia camphorate for antroquinonol production After optimization, the yield of antroquinonol was increased 232.09% when compared with the control (260.57 mg/kg). In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Application In Synthesis of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Application In Synthesis of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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

Identification of the orsellinic acid synthase PKS63787 for the biosynthesis of antroquinonols in Antrodia cinnamomea was written by Yu, Po-Wei;Cho, Ting-Yu;Liou, Ruey-Fen;Tzean, Shean-Shong;Lee, Tzong-Huei. And the article was included in Applied Microbiology and Biotechnology in 2017.Reference of 605-94-7 This article mentions the following:

Antrodia cinnamomea, an endemic basidiomycete used as a health food in Taiwan, is known to synthesize antroquinonols, which were reported to have notable medicinal potential in oncol. and immunol. However, the biosynthetic pathway of these compounds is currently unclear. Our previous study showed that a pks63787 knockout mutant of A. cinnamomea (Δpks63787) is deficient in the biosynthesis of several aromatic metabolites. In this study, we pointed by phylogenetic anal. that pks63787 likely encodes an orsellinic acid synthase. Moreover, amendment of the cultural medium with orsellinic acid not only restores the ability of Δpks63787 to produce its major pigment and other deficient metabolites, e.g., antroquinonols, but also enhances the productivity of several antroquinonols, including 2 new compounds antroquinonols L and M. These results provide direct evidence that the PKS63787 is involved in the biosynthesis of antroquinonols and confirmed our hypothesis that the 6-methylcyclohexenone moiety was synthesized via the PKS63787-mediated polyketide pathway. In conclusion, PKS63787 might function as orsellinic acid synthase and orsellinic acid is an important precursor indispensable for the biosynthesis of the major pigment and antroquinonols in A. cinnamomea. To facilitate further basic or applied study, a putative biosynthesis pathway map of antroquinonols is proposed. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Reference of 605-94-7).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Reference of 605-94-7

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

Cu-Catalyzed Desulfonylative Amination of Benzhydryl Sulfones was written by Nambo, Masakazu;Tahara, Yasuyo;Yim, Jacky C.-H.;Crudden, Cathleen M.. And the article was included in Chemistry – A European Journal in 2019.Recommanded Product: 66943-05-3 This article mentions the following:

A new method for the synthesis of benzhydryl amines I (Ar¹ = Ph Ar² = p-MeC₆H₄, p-MeOC₆H₄, m-F₃CC₆H₄, etc.) from the reaction of readily available sulfone derivatives with amines is described. The Cu-catalyzed desulfonylative amination not only provides structurally diverse benzhydryl amines in good yields, but is also applicable to iterative and intramol. aminations. Control experiments suggested that the formation of a Cu-carbene intermediate generated from the sulfone substrate, which represents a new route for desulfonylative transformations. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Recommanded Product: 66943-05-3).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Recommanded Product: 66943-05-3

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