2iit › Citations

(3R)-4-[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(2,2,2-trifluoroethyl)-1,4-diazepan-2-one, a selective dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes.

Biftu T, Feng D, Qian X, Liang GB, Kieczykowski G, Eiermann G, He H, Leiting B, Lyons K, Petrov A, Sinha-Roy R, Zhang B, Scapin G, Patel S, Gao YD, Singh S, Wu J, Zhang X, Thornberry NA, Weber AE
Bioorg Med Chem Lett 17 49-52 (2007)
Cited: 22 times
EuropePMC logo PMID: 17055272

Abstract

Replacement of the triazolopiperazine ring of sitagliptin (DPP-4 IC(50)=18nM) with 3-(2,2,2-trifluoroethyl)-1,4-diazepan-2-one gave dipeptidyl peptidase IV (DPP-4) inhibitor 1 which is potent (DPP-4 IC(50)=2.6nM), selective, and efficacious in an oral glucose tolerance test in mice. It was selected for extensive preclinical development as a potential back-up candidate to sitagliptin.

Articles - 2iit mentioned but not cited (2)

  1. Identification of novel human dipeptidyl peptidase-IV inhibitors of natural origin (part I): virtual screening and activity assays. Guasch L, Ojeda MJ, González-Abuín N, Sala E, Cereto-Massagué A, Mulero M, Valls C, Pinent M, Ardévol A, Garcia-Vallvé S, Pujadas G. PLoS One 7 e44971 (2012)
  2. Identification of novel human dipeptidyl peptidase-IV inhibitors of natural origin (Part II): in silico prediction in antidiabetic extracts. Guasch L, Sala E, Ojeda MJ, Valls C, Bladé C, Mulero M, Blay M, Ardévol A, Garcia-Vallvé S, Pujadas G. PLoS One 7 e44972 (2012)


Reviews citing this publication (6)

  1. Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes. Havale SH, Pal M. Bioorg Med Chem 17 1783-1802 (2009)
  2. Recent approaches to medicinal chemistry and therapeutic potential of dipeptidyl peptidase-4 (DPP-4) inhibitors. Patel BD, Ghate MD. Eur J Med Chem 74 574-605 (2014)
  3. Dipeptidyl peptidase 4 inhibitors: Applications in innate immunity? Yazbeck R, Jaenisch SE, Abbott CA. Biochem Pharmacol 188 114517 (2021)
  4. Role of Dipeptidyl Peptidase 4 Inhibitors in Antidiabetic Treatment. Yin R, Xu Y, Wang X, Yang L, Zhao D. Molecules 27 3055 (2022)
  5. Activity and selectivity cliffs for DPP-IV inhibitors: Lessons we can learn from SAR studies and their application to virtual screening. Ojeda-Montes MJ, Gimeno A, Tomas-Hernández S, Cereto-Massagué A, Beltrán-Debón R, Valls C, Mulero M, Pujadas G, Garcia-Vallvé S. Med Res Rev 38 1874-1915 (2018)
  6. Novel DPP-4 inhibitors against diabetes. Liu Y, Hu Y. Future Med Chem 6 793-808 (2014)

Articles citing this publication (14)

  1. Inhibition of dipeptidyl peptidase-IV (DPP-IV) by atorvastatin. Taldone T, Zito SW, Talele TT. Bioorg Med Chem Lett 18 479-484 (2008)
  2. Optimization of 1,4-diazepan-2-one containing dipeptidyl peptidase IV inhibitors for the treatment of type 2 diabetes. Liang GB, Qian X, Feng D, Biftu T, Eiermann G, He H, Leiting B, Lyons K, Petrov A, Sinha-Roy R, Zhang B, Wu J, Zhang X, Thornberry NA, Weber AE. Bioorg Med Chem Lett 17 1903-1907 (2007)
  3. Discovery of 3-aminopiperidines as potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitors. Cox JM, Harper B, Mastracchio A, Leiting B, Sinha Roy R, Patel RA, Wu JK, Lyons KA, He H, Xu S, Zhu B, Thornberry NA, Weber AE, Edmondson SD. Bioorg Med Chem Lett 17 4579-4583 (2007)
  4. Identification of diverse dipeptidyl peptidase IV inhibitors via structure-based virtual screening. Li C, Lu W, Lu C, Xiao W, Shen X, Huang J, Liu G, Tang Y. J Mol Model 18 4033-4042 (2012)
  5. Molecular docking studies and 2D analyses of DPP-4 inhibitors as candidates in the treatment of diabetes. Pantaleão SQ, Maltarollo VG, Araujo SC, Gertrudes JC, Honorio KM. Mol Biosyst 11 3188-3193 (2015)
  6. Synthesis and biological evaluation of homopiperazine derivatives with beta-aminoacyl group as dipeptidyl peptidase IV inhibitors. Ahn JH, Park WS, Jun MA, Shin MS, Kang SK, Kim KY, Rhee SD, Bae MA, Kim KR, Kim SG, Kim SY, Sohn SK, Kang NS, Lee JO, Lee DH, Cheon HG, Kim SS. Bioorg Med Chem Lett 18 6525-6529 (2008)
  7. Comprehensive analysis of the Co-structures of dipeptidyl peptidase IV and its inhibitor. Nojima H, Kanou K, Terashi G, Takeda-Shitaka M, Inoue G, Atsuda K, Itoh C, Iguchi C, Matsubara H. BMC Struct Biol 16 11 (2016)
  8. Ephedrine as a lead compound for the development of new DPP-IV inhibitors. Ojeda-Montes MJ, Ardid-Ruiz A, Tomás-Hernández S, Gimeno A, Cereto-Massagué A, Beltrán-Debón R, Mulero M, Garcia-Vallvé S, Pujadas G, Valls C. Future Med Chem 9 2129-2146 (2017)
  9. Approaches towards the development of chimeric DPP4/ACE inhibitors for treating metabolic syndrome. Sattigeri JA, Sethi S, Davis JA, Ahmed S, Rayasam GV, Jadhav BG, Chilla SM, Datta D, Gadhave A, Tulasi VK, Jain T, Voleti S, Benjamin B, Udupa S, Jain G, Singh Y, Srinivas K, Bansal VS, Ray A, Bhatnagar PK, Cliffe IA. Bioorg Med Chem Lett 27 2313-2318 (2017)
  10. Identification of dipeptidyl peptidase IV inhibitors: virtual screening, synthesis and biological evaluation. Xing J, Li Q, Zhang S, Liu H, Zhao L, Cheng H, Zhang Y, Zhou J, Zhang H. Chem Biol Drug Des 84 364-377 (2014)
  11. Improved enzymatic syntheses of valuable beta-arylalkyl-beta-amino acid enantiomers. Tasnádi G, Forró E, Fülöp F. Org Biomol Chem 8 793-799 (2010)
  12. Structural insights of dipeptidyl peptidase-IV inhibitors through molecular dynamics-guided receptor-dependent 4D-QSAR studies. Patil RB, Barbosa EG, Sangshetti JN, Zambre VP, Sawant SD. Mol Divers 22 575-583 (2018)
  13. Discovery of imeglimin-inspired novel 1,3,5-triazine derivatives as antidiabetic agents in streptozotocin-induced diabetes in Wistar rats via inhibition of DPP-4. Gupta A, Bhat HR, Singh UP. RSC Med Chem 14 1512-1536 (2023)
  14. The Effect of Evogliptin Tartrate on Controlling Inflammatory Pain. Cho PG, Jang JH, Ko S, Shin DA, Chung S, Chang MC. Biomedicines 11 2990 (2023)


Quick links