Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol

• Published in: BMC chemistry Vol. 12; no. 1; pp. 95 - 11
• Main Authors: Arumugam, Natarajan, Almansour, Abdulrahman I., Kumar, Raju Suresh, Al-thamili, Dhaifallah M., Periyasami, Govindasami, Periasamy, V. S., Athinarayanan, Jegan, Alshatwi, Ali A., Mahalingam, S. M., Menéndez, J. Carlos
• Format: Journal Article
• Language: English
• Published: Cham Springer International Publishing 01.09.2018; Springer Nature B.V; BMC
• Subjects: Anticancer properties; Antiproliferative activity; Apoptosis; Apoptosis induction; Cancer; Cell death; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Chemo divergent multicomponent reactions; Cycloaddition; Domino reactions; Organic and Medicinal Chemistry; Piperidone; Short Report; Spiropyrrolidine; Stereoselectivity; Chemo divergent multicomponent reactions; Domino reactions; Apoptosis induction; Piperidone; Antiproliferative activity; Spiropyrrolidine
• ISSN: 1752-153X; 1752-153X; 2661-801X
• DOI: 10.1186/s13065-018-0462-x

Background Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their anticancer activity against FaDu hypopharyngeal tumor cells. Findings Interestingly, most compounds displayed cytotoxicities similar to the standard anticancer agent bleomycin, with two of them ( 5a and 5g ) being slightly more active than the reference drug. Conclusion Synthesized compounds have also been evaluated for their apoptosis-inducing properties in a cancer cell model, finding that treatment with compounds 5a – e led to apoptotic cell death.