Ligand-free MCR for linking quinoxaline framework with a benzimidazole nucleus: a new strategy for the identification of novel hybrid molecules as potential inducers of apoptosis

Rajnikanth Sunke; P. Vijaya Babu; Swapna Yellanki; Raghavender Medishetti; Pushkar Kulkarni; Manojit Pal

doi:10.1039/C4OB01268B

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Ligand-free MCR for linking quinoxaline framework with a benzimidazole nucleus: a new strategy for the identification of novel hybrid molecules as potential inducers of apoptosis†

Rajnikanth Sunke,^a P. Vijaya Babu,^ab Swapna Yellanki,^ac Raghavender Medishetti,^ac Pushkar Kulkarni^c and Manojit Pal*^a

Author affiliations

* Corresponding authors

^a Dr. Reddy's Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India
E-mail: manojitpal@rediffmail.com
Tel: +91 40 6657 1500

^b Chemistry Division, Institute of Science and Technology, JNT University, Kukatpally, Hyderabad 500072, India

^c Zephase Therapeutics (an incubated company at the DRILS), University of Hyderabad Campus, Gachibowli, Hyderabad 500046, India

Abstract

We report a true MCR involving the reaction of N-(prop-2-ynyl)quinoxalin-2-amine derivatives with 2-iodoanilines and tosyl azide in the presence of 10 mol% of CuI and Et₃N in DMSO to afford the pre-designed hybrid molecules containing quinoxaline framework linked with a benzimidazole nucleus. The MCR proceeds in the absence of any ligand and/or lateral addition of the catalyst/base affording products within 30 min in good yields, some of which showed encouraging apoptosis inducing properties in zebrafish.

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DOI: https://doi.org/10.1039/C4OB01268B
Article type: Communication
Submitted: 18 Jun 2014
Accepted: 10 Jul 2014
First published: 10 Jul 2014

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Org. Biomol. Chem., 2014,12, 6800-6805

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Ligand-free MCR for linking quinoxaline framework with a benzimidazole nucleus: a new strategy for the identification of novel hybrid molecules as potential inducers of apoptosis

R. Sunke, P. V. Babu, S. Yellanki, R. Medishetti, P. Kulkarni and M. Pal, Org. Biomol. Chem., 2014, 12, 6800 DOI: 10.1039/C4OB01268B

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Organic & Biomolecular Chemistry

Ligand-free MCR for linking quinoxaline framework with a benzimidazole nucleus: a new strategy for the identification of novel hybrid molecules as potential inducers of apoptosis†

Abstract

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Ligand-free MCR for linking quinoxaline framework with a benzimidazole nucleus: a new strategy for the identification of novel hybrid molecules as potential inducers of apoptosis

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