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Vol. 30 No. 9 (2018): Vol 30 Issue 9

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Synthesis, Characterization and Anticancer Activity of 5-Substituted 4,5,6,7-Tetrahydro-N-(tetrahydro-2H-pyran-4-yl)thieno[3,2-c]pyridine-2-carboxamide Derivatives

https://doi.org/10.14233/ajchem.2018.21418
N. Sree Lakshmana Rao
Department of Chemistry, K.L. University, Vaddeswaram, Guntur-522 502, India
Mandava V. Basaveswara Rao
Department of Chemistry, Krishna University, Machilipatnam-521 001, India
K.R.S. Prasad
Department of Chemistry, K.L. University, Vaddeswaram, Guntur-522 502, India

Corresponding Author(s) : Mandava V. Basaveswara Rao

mandavabasaveswararaov@gmail.com

Asian Journal of Chemistry, Vol. 30 No. 9 (2018): Vol 30 Issue 9

Abstract

4,5,6,7-Tetrahydrothieno pyridine (THTP) and their derivatives are an important heterocyclic compounds that exhibits various biological activities viz.,antimicrobial activity, antileishmanial activity, antiarrhythmic activity, antiinflammatory activity, antihyperlipidemic activity, antidepressant activity, anticancer activity, antiplatelet activity and antidiabetic, etc. The present study describes the synthesis, characterization and in vitro cytotoxic potential against human lung carcinoma of some novel derivatives of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (7A-M) with benzylic and amide substitution on the nitrogen atom of tetrahydro theino pyridine ring. The synthetic steps involves (i) Vilsmeyer protocol in step 1 (ii) formation of tetrahydothieno[3,2-c]pyridine ring in presence of 2-mercaptoacetate in step 2 (iii) alkaline hydrolysis followed by amide coupling with tetrahydro-2H-pyran-4-amine in step 3 and step 4. The newly synthesized compounds 7A-M was sufficiently characterized by 1H NMR, IR and mass techniques. Furthermore, these derivatives were screened for their in vitro cytotoxic potential against human lung carcinoma (HCT-116) cell line using the MTT assay. Compound 7B (IC50: 69.52 μg) and compound 7K (IC50: 66.35 μg) exhibited significant activity at micro molar concentration when compared to standard drug camptothecin.

Keywords

Anticancer activity Camptothecin Synthesis Tetrahydothieno[3,2-c]pyridine Villsmeyer-Hack
Lakshmana Rao, N. S., Basaveswara Rao, M. V., & Prasad, K. (2018). Synthesis, Characterization and Anticancer Activity of 5-Substituted 4,5,6,7-Tetrahydro-N-(tetrahydro-2H-pyran-4-yl)thieno[3,2-c]pyridine-2-carboxamide Derivatives. Asian Journal of Chemistry, 30(9), 2063–2068. https://doi.org/10.14233/ajchem.2018.21418
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