Literature DB >> 21071220

A facile 1,3-dipolar cycloaddition of azomethine ylides to 2-arylidene-1,3-indanediones: synthesis of dispiro-oxindolylpyrrolothiazoles and their antimycobacterial evaluation.

Shanmugavel Uma Maheswari1, Kamaraj Balamurugan, Subbu Perumal, Perumal Yogeeswari, Dharmarajan Sriram.   

Abstract

A facile 1,3-dipolar cycloaddition of azomethine ylide generated in situ from the reaction of 1,3-thiazolane-4-carboxylic acid and isatin to 2-arylidene-1,3-indanediones furnished novel dispiro-oxindolylpyrrolothiazoles regio- and stereo-selectively in moderate to good yields (60-92%). In vitro antitubercular screening of 27 compounds against Mycobacterium tuberculosis H37Rv (MTB) disclosed that spiro[5.3']-5'-nitrooxindolespiro-[6.3″]-1H-inden-1″,3″(2H)-dione-7-(4-bromophenyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole has the maximum potency with a minimum inhibitory concentration (MIC) of 1.4 μM against MTB, being 3.4 and 5.4 times more potent than ciprofloxacin and ethambutol, respectively.
Copyright © 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 21071220     DOI： 10.1016/j.bmcl.2010.10.080

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  12 in total

Review 1.  1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments.

Authors:  Fatemeh Rostami Miankooshki; Mohammad Bayat; Shima Nasri; Narges Habibi Samet
Journal:  Mol Divers       Date:  2022-08-04       Impact factor: 3.364

2.  One-pot three-component synthesis and oxidation of functionalized tetrahydrobenzo[d]pyrrolo[2,1-b]thiazoles.

Authors:  Gong Jin; Jing Sun; Yuan Yuan; Dan-Dan He; Chao-Guo Yan
Journal:  Mol Divers       Date:  2018-03-19       Impact factor: 2.943

3.  A green, multicomponent, regio- and stereo-selective 1,3-dipolar cycloaddition of azides and azomethine ylides generated in situ with bifunctional dipolarophiles using PEG-400.

Authors:  Jayant Sindhu; Harjinder Singh; J M Khurana
Journal:  Mol Divers       Date:  2014-02-28       Impact factor: 2.943

4.  A regioselective multicomponent protocol for the synthesis of novel bioactive 4-hydroxyquinolin-2(1H)-one grafted monospiropyrrolidine and thiapyrrolizidine hybrids.

Authors:  Mathan Sankaran; Chokkalingam Uvarani; Kumarasamy Chandraprakash; Swathi U Lekshmi; Sengupta Suparna; James Platts; Palathurai Subramaniam Mohan
Journal:  Mol Divers       Date:  2014-01-14       Impact factor: 2.943

Review 5.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

6.  4'-(4-Bromo-phen-yl)-1'-methyl-dispiro-[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione.

Authors:  Ang Chee Wei; Mohamed Ashraf Ali; Rusli Ismail; Madhukar Hemamalini; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-10-29

7.  Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction.

Authors:  Manjunatha Narayanarao; Lokesh Koodlur; Vijayakumar G Revanasiddappa; Subramanya Gopal; Susmita Kamila
Journal:  Beilstein J Org Chem       Date:  2016-12-29       Impact factor: 2.883

8.  Synthesis of novel (E)-1-(2-(2-(4(dimethylamino) benzylidene) hydrazinyl)-4-methylthiazol-5-yl)ethanone derivatives as ecto-5'-nucleotidase inhibitors.

Authors:  Sidra Hassan; Pervaiz Ali Channar; Fayaz Ali Larik; Aamer Saeed; Hamid Saeed Shah; Joanna Lecka; Jean Sévigny; Jamshed Iqbal
Journal:  R Soc Open Sci       Date:  2018-09-12       Impact factor: 2.963

9.  Design, Synthesis, and Biological Evaluation of Novel Fused Spiro-4H-Pyran Derivatives as Bacterial Biofilm Disruptor.

Authors:  Mohammad Irfan; Parvez Khan; Mohammad Abid; Md Musawwer Khan
Journal:  ACS Omega       Date:  2019-09-30

10.  Stereoselective synthesis of spirocyclic pyrrolidines/pyrrolizidines/pyrrolothiazolidines using l-proline functionalized manganese ferrite nanorods as a novel heterogeneous catalyst.

Authors:  Malihe Akhavan; Ahmadreza Bekhradnia
Journal:  RSC Adv       Date:  2021-04-20       Impact factor: 3.361
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