title: One-Pot Synthesis and Evaluation of Antileishmanial Activities of Functionalized S-Alkyl/Aryl Benzothiazole-2-carbothioate Scaffold.
abstract: The synthesis of hitherto unreported S-alkyl/aryl benzothiazole-2-carbothioate is reported from thiols, oxalyl chloride, and 2-aminothiophenols using 10 mol % n-tetrabutylammonium 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).
authors.affiliation: Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781 039, India.
authors.forename: Ajaz A
authors.initials: AA
authors.lastname: Dar
authors.affiliation: Infectious Diseases and Immunology Division, Indian Institute of Chemical Biology , 4, Raja S.C. Mullick Road, Kolkata 700 032, India.
authors.forename: M
authors.initials: M
authors.lastname: Shadab
authors.affiliation: Department of Chemistry, Pohang University of Science and Technology , Pohang, 37673, Republic of South Korea.
authors.forename: Suman
authors.initials: S
authors.lastname: Khan
authors.affiliation: Infectious Diseases and Immunology Division, Indian Institute of Chemical Biology , 4, Raja S.C. Mullick Road, Kolkata 700 032, India.
authors.forename: Nahid
authors.initials: N
authors.lastname: Ali
authors.affiliation: Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781 039, India.
authors.forename: Abu T
authors.initials: AT
authors.lastname: Khan
mesh_terms: D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001665:Binding Sites; D007893:Leishmania donovani / Q000187:drug effects* / Q000201:enzymology; D007898:Leishmaniasis, Visceral / Q000201:enzymology; D008264:Macrophages / Q000187:drug effects*; D009247:NADH, NADPH Oxidoreductases / Q000737:chemistry* / Q000187:drug effects* / Q000378:metabolism; D009955:Ornithine Decarboxylase / Q000378:metabolism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000981:Antiprotozoal Agents; D052160:Benzothiazoles; D013438:Sulfhydryl Compounds; D009247:NADH, NADPH Oxidoreductases; C049608:trypanothione reductase; D009955:Ornithine Decarboxylase