title: Aza-annulation on the 16-dehydropregnenolone, via tandem intermolecular aldol process and intramolecular Michael addition.
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.
authors: Medicinal and Process Chemistry Division, Central Drug Research Institute, CSIR, Lucknow 226 001, India.
authors: Manmeet
authors: M
authors: Kumar
authors: Preeti
authors: P
authors: Rawat
authors: Mohammad Faheem
authors: MF
authors: Khan
authors: Arun Kumar
authors: AK
authors: Rawat
authors: Arvind Kumar
authors: AK
authors: Srivastava
authors: Rakesh
authors: R
authors: Maurya
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D003500:Cyclization; D018819:Dipeptidyl Peptidase 4 / Q000737:chemistry* / Q000378:metabolism; D054873:Dipeptidyl-Peptidase IV Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011284:Pregnenolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000447:Aldehydes; D000588:Amines; D001372:Aza Compounds; D054873:Dipeptidyl-Peptidase IV Inhibitors; C003592:16-dehydropregnenolone; D011284:Pregnenolone; C116609:3-hydroxybutanal; D018819:Dipeptidyl Peptidase 4