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Synthesis and biological evaluation of novel active arylidene derivatives of 5,6-dihydro-4H-cyclopenta[b]- and 4,5,6,7-tetrahydrobenzo[b]-thiophene-2-carboxylic acid

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A series of novel arylidene derivatives of 5,6-dihydro-4H-cyclopenta[b]-thiophene-2-carboxylic acid and 4,5,6,7-tetrahydrobenzo[b]-thiophene-2-carboxylic acid were synthesized by reacting benzylidene derivatives of chloro aldehyde with 2-mercaptoacetic acid. Benzylidene derivatives of chloro aldehyde were prepared from Vilsmeier reaction of 2-benzylidenecyclopentanone and 2-benzylidenecyclohexanone derivatives, obtained from condensation of various aromatic aldehydes with cyclopentanone and cyclohexanone. All synthesized compounds were characterized by nuclear magnetic resonance (NMR), infrared (IR), and mass spectroscopy and X-ray single-crystal analysis. The synthesized compounds were screened for their in vitro antimicrobial and antifungal activity. Good antimicrobial activity, especially against methicillin-resistant Staphylococcus aureus, was observed for most of the compounds tested. In particular, compound 9f emerged as an effective antibacterial agent and may be a potential candidate for future drug discovery and development.

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The authors thank the management of Orchid Pharma Limited, Chennai-600119, India and Ramakrishna Mission Vivekananda College, Chennai-600004, India for providing the required facilities. We also thank Mr. T. Shanmuganathan for helping carry out the reactions and Mr. T. G. Rajaraman, Dr. K. Parathasarathy, Mr. N. Dhatchanamoorthy, and Mrs. B. Jeyaseeli for helping with manuscript preparation.

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Correspondence to P. R. Kathiravan.

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Kathiravan, P.R., Venugopal, M. & Muthukumaran, S. Synthesis and biological evaluation of novel active arylidene derivatives of 5,6-dihydro-4H-cyclopenta[b]- and 4,5,6,7-tetrahydrobenzo[b]-thiophene-2-carboxylic acid. Res Chem Intermed 43, 2315–2331 (2017).

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