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One-Pot Synthesis and Evaluation of Antileishmanial Activities of Functionalized S‑Alkyl/Aryl Benzothiazole-2-carbothioate Scaffold

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Title One-Pot Synthesis and Evaluation of Antileishmanial Activities of Functionalized S‑Alkyl/Aryl Benzothiazole-2-carbothioate Scaffold
 
Creator Dar, Ajaz A
Shadab, M
Khan, Suman
Ali, Nahid
Khan, T
 
Subject Infectious Diseases and Immunology
 
Description The synthesis of hitherto unreported S-alkyl/
aryl benzothiazole-2-carbothioate is reported from thiols,
oxalyl chloride, and 2-aminothiophenols using 10 mol % ntetrabutylammonium iodide (TBAI) as catalyst in acetonitrile through multicomponent reaction (MCR) strategy. The present protocol favored formation of benzothiazoles and thioesters via simultaneous formation of C−N and C−S bonds in good yields with a wide range of substrates. A few of the synthesized derivatives were evaluated for their antimicrobial activity against the protozoan parasite Leishmania donovani, a causative agent of visceral leishmaniasis (VL). Further, these
compounds displayed no toxicity toward macrophage RAW
264.7 cells and are therefore nontoxic and effective antileishmanial leads. In silico docking studies were performed to understand the possible binding site interaction with trypanothione reductase (TryR).
 
Publisher American Chemical Society
 
Date 2016
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/2496/1/JOURNAL_OF_ORGANIC_CHEMISTRY__Volume__81____Issue__8____Pages__3149%2D3160_.pdf
Dar, Ajaz A and Shadab, M and Khan, Suman and Ali, Nahid and Khan, T (2016) One-Pot Synthesis and Evaluation of Antileishmanial Activities of Functionalized S‑Alkyl/Aryl Benzothiazole-2-carbothioate Scaffold. The Journal of Organic Chemistry, 81 (8). pp. 3149-3160.
 
Relation http://dx.doi.org/10.1021/acs.joc.6b00113
http://www.eprints.iicb.res.in/2496/