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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 4
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Articles

Dicationic liquid mediated synthesis of tetrazoloquinolinyl methoxy phenyl 4-thiazolidinones and their antibacterial and antitubercular evaluation

, , , , &
Pages 587-601 | Received 10 Oct 2018, Published online: 29 Jan 2019
 

Abstract

In a search of new potentially active antitubercular agents here we have synthesized 3-substituted phenyl-2-(4-(tetrazolo[1,5-a]quinolin-4-ylmethoxy)phenyl)thiazolidin-4-ones (8a-l) and evaluated their antibacterial, particularly antitubercular activity. These have been conveniently synthesized by performing one-pot cyclocondensation of 4-(tetrazolo[1,5-a]quinolin-4-ylmethoxy)benzaldehyde, anilines and mercaptoacetic acid in dicationic ionic liquid, (3-methyl-1-[3-(methyl-1H-imidazolium-1-yl)propyl]-1H-imidazolium dibromide [C3(MIM)2-2Br]) and obtained excellent yields of (8a-l). 4-Thiazolidinones (8a-l) were thoroughly characterized by their spectral analyses. These compounds have been screened for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Ra and Mycobacterium bovis (BCG). The compounds 8a, 8c, and 8e exhibited notable in vitro antitubercular activity compare to the reference, Rifampicin. Molecular docking study has also been performed to know the binding mode of these analogs in to the active site of DprE1 enzyme. The synthesized compounds were also evaluated for their in vitro antibacterial activity and amongst them compound 8k has shown moderate activity against both gram-negative and gram-positive bacterial strains.

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Acknowledgements

Authors are thankful to Professor D. B. Ingle for his invaluable discussions and guidance. Authors are also very much grateful to CSIR-National Chemical Laboratory, Pune for providing screening data of synthesized compounds. One of the authors ARD is also grateful to Wockhardt Research Centre, Aurangabad and Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, for awarding research fellowship.

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