Synthesis and cytotoxicity of thieno[2,3-b]quinoline-2-carboxamide and cycloalkyl[b]thieno[3,2-e]pyridine-2-carboxamide derivatives

Leung, Euphemia; Pilkington, Lisa I.; van Rensburg, Michelle; Jeon, Chae Yeon; Song, Mirae; Arabshahi, Homayon J.; De Zoysa, Gayan Heruka; Sarojini, Vijayalekshmi; Denny, William A.; Reynisson, Jóhannes; Barker, David

Abstract

Seventy nine derivatives of thieno[2,3-b]quinolines, tetrahydrothieno[2,3-b]quinoline, dihydrocyclopenta[b]thieno[3,2-e]pyridine, cyclohepta[b]thieno[3,2-e]pyridine and hexahydrocycloocta[b]thieno[3,2-e]pyridine were either synthesized or obtained commercially and tested for their antiproliferative activity against HCT116, MDA-MB-468 and MDA-MB-231 human cancer cell lines. The most potent eight compounds were active against all cell lines with IC50 values in the 80–250 nM range. In general hexahydrocycloocta[b]thieno[3,2-e]pyridines were most active with increasing activity observed as larger cycloalkyl rings were fused to the pyridine ring.

Citation

Leung, E., Pilkington, L. I., van Rensburg, M., Jeon, C. Y., Song, M., Arabshahi, H. J., …Barker, D. (2016). Synthesis and cytotoxicity of thieno[2,3-b]quinoline-2-carboxamide and cycloalkyl[b]thieno[3,2-e]pyridine-2-carboxamide derivatives. Bioorganic and Medicinal Chemistry, 24(5), 1142-1154. https://doi.org/10.1016/j.bmc.2016.01.047

• Journal Article Type: Article
• Acceptance Date: Jan 26, 2016
• Online Publication Date: Jan 27, 2016
• Publication Date: Mar 1, 2016
• Deposit Date: Nov 30, 2023
• Journal: Bioorganic & Medicinal Chemistry
• Print ISSN: 0968-0896
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 24
• Issue: 5
• Pages: 1142-1154
• DOI: https://doi.org/10.1016/j.bmc.2016.01.047
• Keywords: Organic Chemistry; Clinical Biochemistry; Drug Discovery; Pharmaceutical Science; Molecular Biology; Molecular Medicine; Biochemistry
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0968089616300621?via%3Dihub
• Additional Information: This article is maintained by: Elsevier; Article Title: Synthesis and cytotoxicity of thieno[2,3-b]quinoline-2-carboxamide and cycloalkyl[b]thieno[3,2-e]pyridine-2-carboxamide derivatives; Journal Title: Bioorganic & Medicinal Chemistry; CrossRef DOI link to publisher maintained version: https://doi.org/10.1016/j.bmc.2016.01.047; Content Type: article; Copyright: Copyright © 2016 Elsevier Ltd. All rights reserved.