2. Academic Validation
  3. One-pot synthesis of novel tert-butyl-4-substituted phenyl-1H-1,2,3-triazolo piperazine/piperidine carboxylates, potential GPR119 agonists

One-pot synthesis of novel tert-butyl-4-substituted phenyl-1H-1,2,3-triazolo piperazine/piperidine carboxylates, potential GPR119 agonists

  • Bioorg Med Chem Lett. 2019 Dec 1;29(23):126707. doi: 10.1016/j.bmcl.2019.126707.
Nagaraju Bashetti 1,  J V Shanmukha Kumar 1,  Naresh Varma Seelam 1,  B Prasanna 1,  Akiva Mintz 2,  Naresh Damuka 3,  Sriram Devanathan 4,  Kiran Kumar Solingapuram Sai 5
Affiliations

Affiliations

  • 1 Department of Chemistry, Koneru Lakshmaiah Education Foundation, Andhra Pradesh 522502, India.
  • 2 Department of Radiology, Columbia University Medical Center, New York, NY, USA.
  • 3 Department of Radiology, Wake Forest School of Medicine, Winston Salem, NC, USA.
  • 4 Medical Guidance Systems LLC, St. Louis, MO, USA.
  • 5 Department of Radiology, Wake Forest School of Medicine, Winston Salem, NC, USA. Electronic address: ksolinga@wakehealth.edu.
PMID: 31630858 DOI: 10.1016/j.bmcl.2019.126707
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.

Keywords

Agonist; Click chemistry; GPR119; PET.

Figures