Abstract
Pyridines and pyrazines substituted with 1,2,4-oxadiazole-5-ones, 1,2,4-oxadiazole-5-thiones, and 1,3,4-oxathiazoline-2-ones were synthesized and tested against Mycobacterium tuberculosis. The two former ring systems were documented in the literature to act as carboxylic acid isosteres. The latter series was synthesized as possible synthetic intermediates to 1,2,4-thiadiazole-3-ones and was included in this study due to their interesting activity. Pivaloyloxymethyl derivatives of the isosteres were also prepared in order to increase their lipophilicity and therefore improve their cellular permeability. The derivatized isosteres were expected to be biotransformed by esterases to the active species after penetration of the mycobacterial cell wall. Biological properties of the compounds were compared with the unmodified polar isosteres of pyrazinoic and nicotinic acids. The majority of the compounds exhibited activities ranging from 0.5 to 16 times the potency of pyrazinamide.
References
Oct 2, 1992·Journal of Medicinal Chemistry·P C UnangstD J Schrier
Apr 3, 1992·Journal of Medicinal Chemistry·S W FelmanJ Ward
Aug 1, 1991·Journal of Medicinal Chemistry·D J CariniR R Wexler
Apr 1, 1983·Medicinal Research Reviews·R D Allan, G A Johnston
Aug 20, 1993·Journal of Medicinal Chemistry·J W EllingboeJ Wrenn
Dec 20, 1996·Journal of Medicinal Chemistry·Y KoharaT Naka
May 1, 1997·Antimicrobial Agents and Chemotherapy·L Collins, S G Franzblau
Jan 1, 1997·Tubercle and Lung Disease : the Official Journal of the International Union Against Tuberculosis and Lung Disease·K HiranoC Abe
Citations
Sep 25, 2004·Medicinal Research Reviews·Rama P TripathiVinod K Tiwari
Apr 4, 2013·Journal of Medicinal Chemistry·Sevil OzcanSaïd M Sebti
Mar 24, 2011·Future Medicinal Chemistry·Prem M S ChauhanMoni Sharma
Mar 1, 2012·European Journal of Medicinal Chemistry·Antonio Palumbo PiccionelloAndrea Pace
Aug 5, 2008·Tuberculosis·Woo Jin ChungJohn Welch
Aug 23, 2016·ACS Combinatorial Science·Andrey TolmachevYurii S Moroz
Apr 5, 2016·Biological & Pharmaceutical Bulletin·Marwa Sayed Salem, Mohamed Ahmed Mohamed Ali
Apr 30, 2015·Chemical Communications : Chem Comm·Wei GuoHuanfeng Jiang
Oct 16, 2009·Organic & Biomolecular Chemistry·Andrea Pace, Paola Pierro
Sep 8, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Alessio TerenziAndrea Pace
Sep 23, 2014·Chemical Communications : Chem Comm·K K Durga Rao ViswanadhamSurendar Reddy Bathula
Nov 20, 2012·Chemistry & Biodiversity·Halimah SayahiJohn T Welch
Aug 8, 2015·ChemistryOpen·Francesco RussoMats Larhed
Feb 7, 2020·Bioorganic Chemistry·Nayera W HassanSoad A El-Hawash
Feb 27, 2021·Journal of the American Chemical Society·Huamin WangAiwen Lei
Feb 13, 2007·Bioorganic & Medicinal Chemistry·Yves L Janin