Synthesis and biological evaluation of homopiperazine derivatives with β-aminoacyl group as dipeptidyl peptidase IV inhibitors

  • Ahn, Jin Hee; 
  • Park, Woul Seong; 
  • Jun, Mi Ae; 
  • Shin, Mi Sik; 
  • Kang, Seung Kyu; 
  • ... Lee, Duck Hyung; 
  • 외 11명
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초록

Compounds with homopiperazine skeleton are designed to find a potent DPP-IV inhibitor without inhibiting CYP. Thus a series of beta-aminoacyl-containing homopiperazine derivatives was synthesized and evaluated. Compounds with acid moiety were found to be potent inhibitors of DPP-IV without inhibiting CYP 3A4. More specifically, compound 7m showed nanomolar activity with no inhibition towards five sub-types of CYPs, was considered as a prototype for further derivatization. Based on its X-ray co-crystal structure with human DPP-IV, we identified compounds 7s and 7t which showed good in vitro activity, no CYP inhibition, and good selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

키워드

Dipeptidyl peptidase IV; Diabetes; Inhibitor; Homopiperazine; GLUCAGON-LIKE PEPTIDE-1; GLUCOSE-TOLERANCE; DISCOVERY; DESIGN; POTENT
제목
Synthesis and biological evaluation of homopiperazine derivatives with β-aminoacyl group as dipeptidyl peptidase IV inhibitors
저자
Ahn, Jin Hee; Park, Woul Seong; Jun, Mi Ae; Shin, Mi Sik; Kang, Seung Kyu; Kim, Ki Young; Dal Rhee, Sang; Bae, Myung Ae; Kim, Kwang Rok; Kim, Sung Gyu; Kim, Sun Young; Sohn, Sang Kwon; Kang, Nam Sook; Lee, Jie Oh; Lee, Duck Hyung; Cheon, Hyae Gyeong; Kim, Sung Soo
DOI
10.1016/j.bmcl.2008.10.076
발행일
2008-12-15
유형
Article
저널명
Bioorganic & Medicinal Chemistry Letters
권
18
호
24
페이지
6525 ~ 6529