PMID: 11923063Mar 30, 2002Paper

Synthesis of 1,3-thiazine derivatives and their evaluation as potential antimycobacterial agents

European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences
Mamoru KoketsuHideharu Ishihara

Abstract

A series of eight 5,6-dihydro-4H-1,3-thiazine derivatives was synthesized by the BF3 x Et2O-catalyzed reaction of selected alpha,beta-unsaturated ketones with thiobenzamide at room temperature. The antimycobacterial activities of these compounds were determined against Mycobacterium tuberculosis H37Rv (ATCC 27294) using the Alamar blue susceptibility assay. Three compounds, 5-hydroxy-3-phenyl-4-aza-2-thiabicyclo[3.3.1]none-3-ene 3a, 4-hydroxy-4-methyl-6-pentyl-2-phenyl-5,6-dihydro-4H-1,3-thiazine 3b, and 4-ethyl-4-hydroxy-2-phenyl-5,6-dihydro-4H-1,3-thiazine 3c exhibited inhibitory activities of 97, 77 and 76%, respectively, at a concentration of 6.25 microg/ml. The actual MIC99 for the most active of these compounds, 3a, was also determined to be >6.25 microg/ml. These results, and especially those for 3a, suggest that 1,3-thiazines are potential lead compounds in the search for new antitubercular agents.

References

Dec 1, 1995·Antimicrobial Agents and Chemotherapy·J L VennerstromJ A Williams
Jun 6, 1998·The New England Journal of Medicine·D E Snider, K G Castro

❮ Previous
Next ❯

Citations

Nov 8, 2011·Acta Crystallographica. Section E, Structure Reports Online·A ChitradeviS Perumal
May 27, 2005·Antimicrobial Agents and Chemotherapy·Lluis BallellRobert J Young
Mar 24, 2011·Future Medicinal Chemistry·Prem M S ChauhanMoni Sharma
Jul 21, 2010·Bioorganicheskaia khimiia·Sh H Abdel-Hafez
Sep 9, 2011·Bioorganicheskaia khimiia·S H Abdel-HafezM R E Aly
Jan 25, 2020·Beilstein Journal of Organic Chemistry·María C MolloLiliana R Orelli
Aug 19, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Syed Lal Badshah, Abdul Naeem
Jan 21, 2014·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Artem O SurovGerman L Perlovich
Sep 18, 2018·Medicinal Chemistry Research : an International Journal for Rapid Communications on Design and Mechanisms of Action of Biologically Active Agents·Arkadiusz CzerwonkaWojciech Rzeski
Feb 10, 2021·Chemometrics and Intelligent Laboratory Systems : an International Journal Sponsored by the Chemometrics Society·Samir ChtitaTahar Lakhlifi
Sep 10, 2009·Chemical Reviews·Marcos A P MartinsPablo Machado
Aug 24, 2021·Acta Crystallographica. Section E, Crystallographic Communications·R SribalaR V Krishnakumar

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antitubercular Agents (ASM)

Antitubercular agents are pharmacologic agents for treatment of tuberculosis. Discover the latest research on antitubercular agents here.

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antitubercular Agents

Antitubercular agents are pharmacologic agents for treatment of tuberculosis. Discover the latest research on antitubercular agents here.