One-pot synthesis of novel tert-butyl-4-substituted phenyl-1H-1, 2, 3-triazolo piperazine/piperidine carboxylates, potential GPR119 agonists. Issue 23 (1st December 2019)

• Record Type: Journal Article
• Authors: Bashetti, Nagaraju; Shanmukha Kumar, J.V.; Seelam, Naresh Varma; Prasanna, B.; Mintz, Akiva; Damuka, Naresh; Devanathan, Sriram; Solingapuram Sai, Kiran Kumar
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 29:Issue 23(2019)
• Publication Date: 2019-12-01
• Subjects: PET -- Click chemistry -- Agonist -- GPR119; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2019.126707
• Languages: English
• ISSNs: 0960-894X

Abstract

Abstract: We have synthesized a new series of 1, 2, 3-triazolo piperazine and piperidine carboxylate derivatives using a simple and one-pot click chemistry with significantly reduced reaction times (~5 min) and enhanced reaction yields (~95–98%). The fourteen novel compounds thus synthesized were tested for ability to target GPR119, a G-protein coupled target receptor that plays critical role in regulation of type-2 diabetes mellitus. Four analogs (3e, 3g, 5e and 5g) demonstrated similar or better EC50 values over previously reported AR231453 activity towards GPR119. Graphical abstract: We have synthesized a new series of 1, 2, 3-triazolo piperazine and piperidine carboxylate derivatives using a simple and one-pot click chemistry with significantly reduced reaction times (~5 min) and enhanced reaction yields (~95–98%). The fourteen novel compounds thus synthesized were tested for ability to target GPR119, a G-protein coupled target receptor that plays critical role in regulation of type-2 diabetes mellitus. Four analogs (3e, 3g, 5e and 5g) demonstrated similar or better EC50 values over previously reported AR231453 activity towards GPR119. Unlabelled Image