Aza-annulation on the 16-dehydropregnenolone, via tandem intermolecular aldol process and intramolecular Michael addition

Manmeet Kumar; Preeti Rawat; Mohammad Faheem Khan; Arun Kumar Rawat; Arvind Kumar Srivastava; Rakesh Maurya

doi:10.1016/j.bmcl.2011.02.112

Aza-annulation on the 16-dehydropregnenolone, via tandem intermolecular aldol process and intramolecular Michael addition

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2232-7. doi: 10.1016/j.bmcl.2011.02.112. Epub 2011 Mar 4.

Authors

Manmeet Kumar¹, Preeti Rawat, Mohammad Faheem Khan, Arun Kumar Rawat, Arvind Kumar Srivastava, Rakesh Maurya

Affiliation

¹ Medicinal and Process Chemistry Division, Central Drug Research Institute, CSIR, Lucknow 226 001, India.

PMID: 21435872
DOI: 10.1016/j.bmcl.2011.02.112

Abstract

16-Dehydropregnenolone undergoes a smooth annulation with propan-1-amine and aromatic aldehydes. Several amine derivatives of 16- dehydropregnenolone were synthesized and evaluated as inhibitors of DPP-IV. The structures of compounds were confirmed by (1)H, (13)C, NMR and mass spectral analysis. Among 17 compounds evaluated only five compounds 1, 9, 13, 15 and 16 demonstrated significant inhibition of DPP. This study suggest that introduction of appropriate substituents in the 16-dehydropregnenolone plays an important role in DPP-IV inhibitory activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Amines / chemistry
Aza Compounds / chemistry*
Cyclization
Dipeptidyl Peptidase 4 / chemistry*
Dipeptidyl Peptidase 4 / metabolism
Dipeptidyl-Peptidase IV Inhibitors / chemical synthesis
Dipeptidyl-Peptidase IV Inhibitors / chemistry*
Dipeptidyl-Peptidase IV Inhibitors / pharmacology
Pregnenolone / analogs & derivatives*
Pregnenolone / chemical synthesis
Pregnenolone / chemistry
Pregnenolone / pharmacology

Substances

Aldehydes
Amines
Aza Compounds
Dipeptidyl-Peptidase IV Inhibitors
16-dehydropregnenolone
Pregnenolone
3-hydroxybutanal
Dipeptidyl Peptidase 4