Literature DB >> 16595643

Synthesis and antileprosy activity of some dialkyldithiocarbamates.

Vadim Makarov1, Olga B Riabova, Anatoly Yuschenko, Nailya Urlyapova, Adilya Daudova, Peter F Zipfel, Ute Möllmann.   

Abstract

OBJECTIVES: To investigate the antileprosy potential of a set of original compounds with antimycobacterial activity.
METHODS: We developed a facile synthesis of 2-chloro-3-cyano-5-nitropyridine and synthesized a series of 3-cyano-2-dialkyldithiocarbamoyl-5-nitropyridine derivatives. In vivo therapeutic efficacy against Mycobacterium leprae was assessed in the infected mouse footpad model.
RESULTS: The compounds were active in vitro against Mycobacterium smegmatis, Mycobacterium aurum, Mycobacterium vaccae and Mycobacterium fortuitum, with MICs generally in the range of 0.4-6.25 mg/L. Reduction of the bacterial load in vivo in the mouse footpad and toxic side effects were dependent on the individual structure of the compounds and on the doses applied. Compounds 2a, 3a and 3b reduced the number of M. leprae by two orders of magnitude, comparable to the effect of dapsone. Co-administration of compounds 2a and 3a with dapsone synergistically enhanced the activity. In addition, these compounds were well tolerated over the treatment period of 7.5 months.
CONCLUSIONS: Individual synthetic dithiocarbamate derivatives have promising antileprosy activity.

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Year:  2006        PMID: 16595643     DOI: 10.1093/jac/dkl095

Source DB:  PubMed          Journal:  J Antimicrob Chemother        ISSN: 0305-7453            Impact factor:   5.790


  11 in total

1.  New 2-thiopyridines as potential candidates for killing both actively growing and dormant Mycobacterium tuberculosis cells.

Authors:  Elena Salina; Olga Ryabova; Arseny Kaprelyants; Vadim Makarov
Journal:  Antimicrob Agents Chemother       Date:  2013-10-14       Impact factor: 5.191

2.  Spirocyclic and Bicyclic 8-Nitrobenzothiazinones for Tuberculosis with Improved Physicochemical and Pharmacokinetic Properties.

Authors:  Gang Zhang; Michael Howe; Courtney C Aldrich
Journal:  ACS Med Chem Lett       Date:  2019-02-23       Impact factor: 4.345

3.  Deuteration of BTZ043 Extends the Lifetime of Meisenheimer Intermediates to the Antituberculosis Nitroso Oxidation State.

Authors:  Rui Liu; Viktor Krchnak; Seth N Brown; Marvin J Miller
Journal:  ACS Med Chem Lett       Date:  2019-08-29       Impact factor: 4.345

4.  Machine Learning Models for Mycobacterium tuberculosis In Vitro Activity: Prediction and Target Visualization.

Authors:  Thomas R Lane; Fabio Urbina; Laura Rank; Jacob Gerlach; Olga Riabova; Alexander Lepioshkin; Elena Kazakova; Anthony Vocat; Valery Tkachenko; Stewart Cole; Vadim Makarov; Sean Ekins
Journal:  Mol Pharm       Date:  2021-12-29       Impact factor: 5.364

5.  Benzothiazinones kill Mycobacterium tuberculosis by blocking arabinan synthesis.

Authors:  Vadim Makarov; Giulia Manina; Katarina Mikusova; Ute Möllmann; Olga Ryabova; Brigitte Saint-Joanis; Neeraj Dhar; Maria Rosalia Pasca; Silvia Buroni; Anna Paola Lucarelli; Anna Milano; Edda De Rossi; Martina Belanova; Adela Bobovska; Petronela Dianiskova; Jana Kordulakova; Claudia Sala; Elizabeth Fullam; Patricia Schneider; John D McKinney; Priscille Brodin; Thierry Christophe; Simon Waddell; Philip Butcher; Jakob Albrethsen; Ida Rosenkrands; Roland Brosch; Vrinda Nandi; Sowmya Bharath; Sheshagiri Gaonkar; Radha K Shandil; Venkataraman Balasubramanian; Tanjore Balganesh; Sandeep Tyagi; Jacques Grosset; Giovanna Riccardi; Stewart T Cole
Journal:  Science       Date:  2009-03-19       Impact factor: 47.728

6.  Decaprenylphosphoryl-β-D-ribose 2'-epimerase, the target of benzothiazinones and dinitrobenzamides, is an essential enzyme in Mycobacterium smegmatis.

Authors:  Paul K Crellin; Rajini Brammananth; Ross L Coppel
Journal:  PLoS One       Date:  2011-02-08       Impact factor: 3.240

7.  Resistance in tuberculosis: what do we know and where can we go?

Authors:  Keith D Green; Sylvie Garneau-Tsodikova
Journal:  Front Microbiol       Date:  2013-07-23       Impact factor: 5.640

8.  Towards a new combination therapy for tuberculosis with next generation benzothiazinones.

Authors:  Vadim Makarov; Benoit Lechartier; Ming Zhang; João Neres; Astrid M van der Sar; Susanne A Raadsen; Ruben C Hartkoorn; Olga B Ryabova; Anthony Vocat; Laurent A Decosterd; Nicolas Widmer; Thierry Buclin; Wilbert Bitter; Koen Andries; Florence Pojer; Paul J Dyson; Stewart T Cole
Journal:  EMBO Mol Med       Date:  2014-02-05       Impact factor: 12.137

9.  Finding of the low molecular weight inhibitors of resuscitation promoting factor enzymatic and resuscitation activity.

Authors:  Galina R Demina; Vadim A Makarov; Vadim D Nikitushkin; Olga B Ryabova; Galina N Vostroknutova; Elena G Salina; Margarita O Shleeva; Anna V Goncharenko; Arseny S Kaprelyants
Journal:  PLoS One       Date:  2009-12-16       Impact factor: 3.240

Review 10.  Hit Generation in TB Drug Discovery: From Genome to Granuloma.

Authors:  Tianao Yuan; Nicole S Sampson
Journal:  Chem Rev       Date:  2018-01-31       Impact factor: 60.622

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