32955-22-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 5939, 1984 DOI: 10.1016/S0040-4039(01)81726-3

InChI:InChI=1/C6H7NO2S/c1-2-9-6(8)5-3-7-4-10-5/h3-4H,2H2,1H3

Upstream product

• 115-08-2 thiocarboxamide 
• 33142-21-1 ethyl 2-chloro-3-oxopropanoate 
• 3034-55-7 5-bromo-1,3-thiazole 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 32955-21-8 2-amino-thiazole-5-carboxylic acid ethyl ester 
• 110-46-3 isopentyl nitrite 
• 77287-34-4 formamide 
• 188290-36-0 thiophene 
• 83553-48-4 ethyl 2-iodothiazole-5-carboxylate 

Downstream Products

• 38585-74-9 thiazol-5-yl-methanol 
• 14527-41-4 thiazole-5-carboxylic acid 
• 74411-19-1 thiazole-5-carboxamide 

Relevant academic research and scientific papers

Synthesis, Antiviral Potency, in Vitro ADMET, and X-ray Structure of Potent CD4 Mimics as Entry Inhibitors That Target the Phe43 Cavity of HIV-1 gp120

In our attempt to optimize the lead HIV-1 entry antagonist, NBD-11021, we present in this study the rational design and synthesis of 60 new analogues and determination of their antiviral activity in a single-cycle and a multicycle infection assay to derive a comprehensive structure-activity relationship (SAR). Two of these compounds, NBD-14088 and NBD-14107, showed significant improvement in antiviral activity compared to the lead entry antagonist in a single-cycle assay against a large panel of Env-pseudotyped viruses. The X-ray structure of a similar compound, NBD-14010, confirmed the binding mode of the newly designed compounds. The in vitro ADMET profiles of these compounds are comparable to that of the most potent attachment inhibitor BMS-626529, a prodrug of which is currently undergoing phase III clinical trials. The systematic study presented here is expected to pave the way for improving the potency, toxicity, and ADMET profile of this series of compounds with the potential to be moved to the early preclinical development.

Synthesis and antibacterial activities of pleuromutilin derivatives with thiazole-5-carboxamide and thioether moiety

Seven novel pleuromutilin derivatives with thiazole-5-carboxamide and thioether moiety in the C14 side chain were designed and synthesised. The antibacterial activities of the target compounds were tested via agar-well diffusion method in vitro. The results showed that three target compounds still had antibacterial activity against Staphylococcus aureus ATCC26112 and Staphylococcus aureus SC at a low concentration of 0.05 μg mL-1.

Tandem photoarylation-photoisomerization of halothiazoles: Synthesis, photophysical and singlet oxygen activation properties of ethyl 2-arylthiazole-5-carboxylates

The photochemical reaction between ethyl 2-chlorothiazole5-carboxylate and benzene gave no product. In contrast, the reaction with ethyl 2-iodothiazole-5-carboxylate gave ethyl 3-phenylisothiazole-4-carboxylate. The same behaviour was observed if the reac

Retroviral protease inhibiting compounds

A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A compound of the formula: STR1 is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

Discovery of ritonavir, a potent inhibitor of HIV protease with high oral bioavailability and clinical efficacy

The structure-activity studies leading to the potent and clinically efficacious HIV protease inhibitor ritonavir are described. Beginning with the moderately potent and orally bioavailable inhibitor A-80987, systematic investigation of peripheral (P3 and P2') heterocyclic groups designed to decrease the rate of hepatic metabolism provided analogues with improved pharmacokinetic properties after oral dosing in rats. Replacement of pyridyl groups with thiazoles provided increased chemical stability toward oxidation while maintaining sufficient aqueous solubility for oral absorption. Optimization of hydrophobic interactions with the HIV protease active site produced ritonavir, with excellent in vitro potency (EC50 = 0.02 μM) and high and sustained plasma concentrations after oral administration in four species. Details of the discovery and preclinical development of ritonavir are described.

Pharmaceutical composition for inhibiting HIV protease

A pharmaceutical composition is disclosed which comprises a solution of an HIV protease inhibiting compound in a pharmaceutically acceptable organic solvent comprising a mixture of (1) (a) a solvent selected from propylene glycol and polyethylene glycol or (b) a solvent selected from polyoxyethyleneglycerol triricinoleate, polyethylene glycol 40 hydrogenated castor oil, fractionated coconut oil, polyoxyethylene (20) sorbitan monooleate and 2-(2-ethoxyethoxy)ethanol or (c) a mixture thereof and (2) ethanol or propylene glycol.

Pharmaceutical composition

A solid pharmaceutical composition is disclosed which comprises a pharmaceutically acceptable adsorbent or a mixture of pharmaceutically acceptable adsorbents to which is adsorbed a mixture of (1) a pharmaceutically acceptable organic solvent or a mixture of pharmaceutically acceptable organic solvents, (2) an HIV protease inhibiting compound and (3) one or more pharmaceutically acceptable acids. The solid composition can optionally be encapsulated in a hard gelatin capsule.

RETROVIRAL PROTEASE INHIBITING PIPERAZINE COMPOUNDS

Retroviral protease inhibiting compounds of the formula: STR1 are disclosed.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A retroviral protease inhibiting compound of the formula: STR1 is disclosed wherein R 1, R 2, R 5, R 6, Y m and Y' n are herein defined.