Issue 72, 2018, Issue in Progress
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RSC Advances

Highly functionalized pyrrolidine analogues: stereoselective synthesis and caspase-dependent apoptotic activity†

Raju Suresh Kumar, ORCID logo *a   Abdulrahman I. Almansour,a   Natarajan Arumugam, ORCID logo a   Faruq Mohammad, ORCID logo b   Waleed Shihan Alshahrani,a   Kotresha D,c   Mohammad Altaf,ad   Mohammad Azama  and  J. Carlos Menéndez ORCID logo e  

* Corresponding authors

a Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia
E-mail: sraju@ksu.edu.sa, drrajusureshkumar@gmail.com

b Surfactant Research Chair, Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia

c Department of Microbiology, East West Group of Institution, No. 63, Anjananagar, Vishwaneedam Post, Bangaluru-560091, Karnataka, India

d Central Laboratory, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia

e Unidad de Química Orgánica y Farmacéutica, Departamento de Química en Ciencias Farmacéuticas, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain

Abstract

Novel spiropyrrolidine heterocyclic hybrids were synthesized for the first time in a sustainable fashion employing a 1,3-dipolar cycloaddition strategy to form a new class of azomethine ylides generated from tyrosine and acenaphthenequinone. Following their synthesis and characterization, these heterocyclic hybrids were tested for their anticancer activities by incubation at different concentrations and durations with different cancer and non-cancer cell cultures, and the results indicated a potential therapeutic activity. Further analysis of cancer cell death revealed that it occurred through a caspase-related apoptotic pathway, specifically mediated by caspase-3. These results demonstrated that the obtained spiropyrrolidine heterocyclic hybrids may be good hit compounds for the development of potential therapeutic agents for the treatment of malignant tumors.

Graphical abstract: Highly functionalized pyrrolidine analogues: stereoselective synthesis and caspase-dependent apoptotic activity

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Article information

DOI
https://doi.org/10.1039/C8RA07985D
Article type
Paper
Submitted
26 Sep 2018
Accepted
03 Dec 2018
First published
10 Dec 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 41226-41236

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Highly functionalized pyrrolidine analogues: stereoselective synthesis and caspase-dependent apoptotic activity

R. S. Kumar, A. I. Almansour, N. Arumugam, F. Mohammad, W. S. Alshahrani, K. D, M. Altaf, M. Azam and J. C. Menéndez, RSC Adv., 2018, 8, 41226 DOI: 10.1039/C8RA07985D

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