76632-23-0

Usage

Uses

Used in Pharmaceutical Industry:
(2-Methyl-1,3-thiazol-4-yl)methanol is used as a reagent in the study of modified arylsulfonamide HIV protease inhibitors. Its unique chemical structure allows it to interact with the active sites of HIV protease, potentially leading to the development of new and more effective antiretroviral drugs. This application is particularly important in the ongoing fight against HIV/AIDS, as the development of new drugs is crucial to combat drug resistance and improve patient outcomes.

InChI:InChI=1/C5H7NOS/c1-4-6-5(2-7)3-8-4/h3,7H,2H2,1H3

Upstream product

• 6436-59-5 ethyl 2-methylthiazole-4-carboxylate 
• 304-59-6 Rochelle's salt 

Downstream Products

• 39238-07-8 4-(chloromethyl)-2-methyl-1,3-thiazole 
• 20949-84-2 2-methylthiazole-4-carbaldehyde 
• 13458-33-8 (2-methyl-4-thiazolyl)acetonitrile 
• 1174764-12-5 (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoic acid 
• 1219930-75-2 methyl (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoate 
• 189453-10-9 epothilone D 
• 152044-54-7 epothilone B 
• 1005323-60-3 C₃₃H₄₄N₄O₈S₂ 
• 1003889-67-5 C₁₂H₁₀N₂O₅S 

Relevant academic research and scientific papers

12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents

The synthesis and biological evaluation of a series of 12,13-aziridinyl epothilone B analogues is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic methyl ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif was achieved by application of the Ess-Kürti-Falck aziridination, while the heterocyclic side chains were introduced via stereoselective phosphonate-based olefinations. In order to ensure high (E) selectivities for the latter reaction for electron-rich heterocycles, it became necessary to develop and apply an unprecedented modification of the venerable Horner-Wadsworth-Emmons reaction, employing 2-fluoroethoxyphosphonates that may prove to be of general value in organic synthesis. These studies resulted in the discovery of some of the most potent epothilones reported to date. Equipped with functional groups to accommodate modern drug delivery technologies, some of these compounds exhibited picomolar potencies that qualify them as payloads for antibody drug conjugates (ADCs), while a number of them revealed impressive activities against drug resistant human cancer cells, making them desirable for potential medical applications.

1-(DIHYDRONAPHTHALENYL)PYRIDONES AS MELANIN-CONCENTRATING HORMONE RECEPTOR 1 ANTAGONISTS

Provided are 1-(dihydronaphthalenyl)pyridones which are antagonists at the melanin-concentrating hormone receptor 1 (MCHR1), pharmaceutical compositions containing them, processes for their preparation, and their use in therapy for the treatment of obesity and diabetes.

PAR4 AGONIST PEPTIDES

The present invention provides PAR4 agonist peptides. These peptides are useful for developing robust PAR4 receptor assays.

IMIDAZOTHIADIAZOLE AND IMIDAZOPYRAZINE DERIVATIVES AS PROTEASE ACTIVATED RECEPTOR 4 (PAR4) INHIBITORS FOR TREATING PLATELET AGGREGATION

The present invention provides thiazole compounds of Formula I wherein W, Y, R0, R2, R4, R5, R6, R7, X1, X2, X3 and X4 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of platelet aggregation and thus can be used as medicaments for treating or preventing thromboembolic disorders.

Design, synthesis, and biological testing of potential heme-coordinating nitric oxide synthase inhibitors

Based on computer modeling of the active site of nitric oxide synthases (NOS), a series of 10 amidine compounds (9-18) was designed including potential inhibitors that involve the coordination of side-chain functional groups with the iron of the heme cofactor. The most potent and selective compound was the methylthio amidine analogue 9, which was more potent than l-nitroarginine with 185-fold selectivity for inhibition of neuronal NOS over endothelial NOS. It also exhibited time-dependent inhibition, but did not involve the mechanism previously proposed for other amidine inhibitors of NOS. None of the compounds, however, exhibited heme-binding characteristics according to absorption spectroscopy.

CHEMOKINE RECEPTOR ANTAGONISTS

A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof, wherein the variants R, R9, Z, X, Q and Y are defined in the specification.

Total syntheses of epothilones B and D

A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.

First synthesis of an amythiamicin pyridine cluster

The pyridine-containing central domain of the amythiamicin group of thiopeptide antibiotics is prepared in protected form in 9 steps, 93% ee and 18% overall yield from (S)-2-[1-(tert-butoxycarbonylamino)-2-methylpropyl] thiazole-4-carboxylic acid by Michael addition-cyclodehydration of a 2-(2-thiazolyl)enamine and 1-(2-thiazolyl)propynone.

Synthesis of Dimethyl Sulfomycinamate

(Equation presented) Dimethyl sulfomycinamate, the oxazole-thiazole- pyridine product generated in the methanolysis of the thiopeptide antibiotic sulfomycin I, is prepared in 13 steps and 8% overall yield by the Bohlmann-Rahtz heteroannulation of 1-(oxazol-4-yl)enamines and methyl 4-(trimethylsilyl)-2-oxobut-3-ynoate.

Bicyclic pyrrole derivatives as MCP-1 inhibitors

A pharmaceutical composition comprising a compound of formula (I): or a pharmaceutically acceptable salt, ester or amide thereof, which is an inhibitor of monocyte chemoattractant protein-1 and wherein A and B together form an optionally substituted 5-member aromatic ring which includes at least one heteroatom; R1is an optionally substituted aryl or heteroaryl ring; R2is selected from a range of organic groups including carboxy, and R3is hydrogen, or a range of organic groups; in combination with a pharmaceutically acceptable carrier. Certain compounds of formula (I) are novel and these form a further aspect of the invention.