3855-26-3Relevant academic research and scientific papers
The Oxidation of Hydrophobic Aromatic Substrates by Using a Variant of the P450 Monooxygenase CYP101B1
Sarkar, Md. Raihan,Lee, Joel H. Z.,Bell, Stephen G.
, p. 2119 - 2128 (2017/10/12)
The cytochrome P450 monooxygenase CYP101B1, from a Novosphingobium bacterium is able to bind and oxidise aromatic substrates but at a lower activity and efficiency than norisoprenoids and monoterpenoid esters. Histidine 85 of CYP101B1 aligns with tyrosine 96 of CYP101A1, which, in the latter enzyme forms the only hydrophilic interaction with its substrate, camphor. The histidine residue of CYP101B1 was mutated to phenylalanine with the aim of improving the activity of the enzyme for hydrophobic substrates. The H85F mutant lowered the binding affinity and activity of the enzyme for β-ionone and altered the oxidation selectivity. This variant also showed enhanced affinity and activity towards alkylbenzenes, styrenes and methylnaphthalenes. For example the rate of product formation for acenaphthene oxidation was improved sixfold to 245 nmol per nmol CYP per min. Certain disubstituted naphthalenes and substrates, such as phenylcyclohexane and biphenyls, were oxidised with lower activity by the H85F variant. Variants at H85 (A and G) designed to introduce additional space into the active site so as to accommodate these larger substrates did not improve the oxidation activity. As the H85F mutant of CYP101B1 improved the oxidation of hydrophobic substrates, this residue is likely to be in the substrate binding pocket or the access channel of the enzyme. The side chain of the histidine might interact with the carbonyl groups of the favoured norisoprenoid substrates of CYP101B1.
Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants
Munday, Samuel D.,Dezvarei, Shaghayegh,Lau, Ian C.-K.,Bell, Stephen G.
, p. 2512 - 2522 (2017/07/12)
Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.
Synthesis, characterization, spectral studies, biocidal Activities of Fe (II) and Cu (II) complexes of Azo dye Ligand Derived from sulfamethoxazole and substituted p-Cresol
Modhavadiya, V. A.
, p. 921 - 925,5 (2020/08/24)
P-Cresyl acetate (I) has been prepared by acetylation of p-Cresol. Fries migration of (I) yields 2-Acetyl-4-methyl phenol (II). Clemmensen's reduction of (II) yields 2-Ethyl-4-methyl phenol (III). Diazonium salt (IV) prepared by diazotizatin of sulfamethoxazole. Azo dye ligand 3-ethyl-2-hydroxy-5-methyl- 4′-( 5″-methyl-oxazolel-3″-yl ) amino sulphonyl azobenzene (V) has been prepared by coupling of 2-Ethyl-4-methyl phenol (III) with Diazonium salt (IV) at 0-5 °CBy refluxing alcoholic solution of ligand with aqueous solution of metal salts yields azo dye ligand complexes (Vl) of ML 2 (H2O)2 or ML2 type. They were characterized by elemental analysis, absorption spectra, conductivity measurement, molecular weight determination and magnetic susceptibility measurements. The ligand as well as the metal complex has been screened for their antimicrobial activity against a number of micro organisms.
THIAZOLE COMPOUNDS USEFUL AS ACETYL-COA CARBOXYLASE (ACC) INHIBITORS
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Page/Page column 87, (2013/03/15)
The present invention provides thiazole compounds of Formula I or its pharmaceutically acceptable salts, prodrugs, solvates, N-oxide thereof; solvates of pharmaceutically acceptable salts and N-oxides; pharmaceutically acceptable salts of N-oxides, or prodrugs; or combination or mixtures thereof; (I) The present invention further provides a method for preventing or treating a condition that responds to an Acetyl-CoA Carboxylase (ACC) inhibitor by using compounds of formula (I) or ), its pharmaceutically acceptable salts, prodrugs, solvates, N-oxide thereof; solvates of pharmaceutically acceptable salts and N-oxides; pharmaceutically acceptable salts of N-oxides, or prodrugs; or combination or mixtures thereof.
Halide-free ethylation of phenol by multifunctional catalysis using phosphinite ligands
Carrion, M. Carmen,Cole-Hamilton, David J.
, p. 4527 - 4529 (2008/09/18)
The ortho-alkylation of phenols or aniline by catalytic C-H activation and multifunctional catalysis is described. The Royal Society of Chemistry 2006.
Catalytic ethylation of phenols
Agaev,Shakhtakhtinskaya,Eminov,Guliev
, p. 651 - 653 (2007/10/03)
Alkylation of phenol and cresols with ethanol in the presence of iron-aluminum catalyst was studied.
ipso Nitration. XXIII. Reactions of cyclohexadiene adducts from nitration of 4-ethyltoluene in acetic anhydride
Fischer, Alfred,Henderson, George N.
, p. 2314 - 2327 (2007/10/02)
The diastereoisomers of 4-ethyl-1-methyl-4-nitrocyclohexa-2,5-dienyl acetate (1) and 1-ethyl-4-methyl-4-nitrocyclohexa-2,5-dienyl acetate (2) are stereospecifically reduced to the corresponding nitrocyclohexadienols with aluminum hydride.Each dienol is stereospecifically methylated to the corresponding methyl ether with methyl iodide, silver oxide, and potassium hydroxide.Acid-catalysed solvolysis of the acetates 1 and 2 results in the substitution of the acetate moiety by other nucleophiles and these reactions are not stereospecific.The products of rearomatization of dienyl acetates, dienols and dienyl methyl ethers depend on the acidity and ionizing power of the solvents and are readily explained in terms of reactions involving a nitrocyclohexadienyl cation or acetoxy- (hydroxy-, methoxy-)cyclohexadienyl cation as key intermediates.In the 4-acetoxy-4-alkylcyclohexadienyl cation 1,2-migration of the acetoxyl group is more rapid then alkyl migration, but 1,2-alkyl migration is faster then migration of the hydroxyl or methoxyl groups in the corresponding cations. 1-Ethyl-4-methoxy-4-methylcyclohexa-2,5-dien-1-ol and 4-ethyl-3-nitrotoluene are significant minor products in the solvolysis of 1-ethyl-4-methyl-4-nitrocyclohexa-2,5-dien-1-ol in aqueous methanol.Nitration of p-ethyltoluene in the presence of sulfuric acid or in trifluoracetic anhydride gives a mixture of 4-ethyl-2-nitro- and 4-ethyl-3-nitrotoluene in a 2:1 ratio.
