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

作者: Ajaz A. Dar , M. Shadab , Suman Khan , Nahid Ali , Abu T. Khan

DOI: 10.1021/ACS.JOC.6B00113

关键词:

摘要: 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. present protocol favored formation benzothiazoles thioesters via simultaneous C–N C–S bonds good yields with a wide range substrates. A few the synthesized derivatives were evaluated for their antimicrobial activity against protozoan parasite Leishmania donovani, causative agent visceral leishmaniasis (VL). Further, these compounds displayed no toxicity toward macrophage RAW 264.7 cells are therefore nontoxic effective antileishmanial leads. In silico docking studies performed to understand possible binding site interaction trypanothione reductase (TryR).

参考文章(72)
Arash Ghorbani-Choghamarani, Zahra Darvishnejad, Masoomeh Norouzi, Cu(II)–Schiff base complex‐functionalized magnetic Fe3O4 nanoparticles: a heterogeneous catalyst for various oxidation reactions Applied Organometallic Chemistry. ,vol. 29, pp. 170- 175 ,(2015) , 10.1002/AOC.3266
Hidayat Hussain, Ahmed Al-Harrasi, Ahmed Al-Rawahi, Ivan R. Green, Simon Gibbons, Fruitful Decade for Antileishmanial Compounds from 2002 to Late 2011 Chemical Reviews. ,vol. 114, pp. 10369- 10428 ,(2014) , 10.1021/CR400552X
Chi B. Vu, Jill C. Milne, David P. Carney, Jeffrey Song, Wendy Choy, Philip D. Lambert, David J. Gagne, Michael Hirsch, Angela Cote, Meghan Davis, Elden Lainez, Nekeya Meade, Karl Normington, Michael R. Jirousek, Robert B. Perni, Discovery of benzothiazole derivatives as efficacious and enterocyte-specific MTP inhibitors. Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 1416- 1420 ,(2009) , 10.1016/J.BMCL.2009.01.044
Xiao-Feng Wu, Jin-Long Gong, Xinxin Qi, A powerful combination: recent achievements on using TBAI and TBHP as oxidation system Organic and Biomolecular Chemistry. ,vol. 12, pp. 5807- 5817 ,(2014) , 10.1039/C4OB00276H
Xin Wang, Guokai Liu, Xiu-Hua Xu, Naoyuki Shibata, Etsuko Tokunaga, Norio Shibata, S‐((Phenylsulfonyl)difluoromethyl)thiophenium Salts: Carbon‐Selective Electrophilic Difluoromethylation of β‐Ketoesters, β‐Diketones, and Dicyanoalkylidenes Angewandte Chemie. ,vol. 53, pp. 1827- 1831 ,(2014) , 10.1002/ANIE.201309875
Wei Xu, Boris J. Nachtsheim, TBAI-Catalyzed Oxidative Cross-Coupling of Phenols and 2-Aminoacetophenones Organic Letters. ,vol. 17, pp. 1585- 1588 ,(2015) , 10.1021/ACS.ORGLETT.5B00466
Richard A. Friesner, Jay L. Banks, Robert B. Murphy, Thomas A. Halgren, Jasna J. Klicic, Daniel T. Mainz, Matthew P. Repasky, Eric H. Knoll, Mee Shelley, Jason K. Perry, David E. Shaw, Perry Francis, Peter S. Shenkin, Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. Journal of Medicinal Chemistry. ,vol. 47, pp. 1739- 1749 ,(2004) , 10.1021/JM0306430
Toru Kawakami, Megumi Sumida, Ken’ichiroh Nakamura, Thomas Vorherr, Saburo Aimoto, Peptide thioester preparation based on an N-S acyl shift reaction mediated by a thiol ligation auxiliary Tetrahedron Letters. ,vol. 46, pp. 8805- 8807 ,(2005) , 10.1016/J.TETLET.2005.09.184