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Aryl- and heteroaryl-substituted aminobenzo[a]quinolizines as dipeptidyl peptidase IV inhibitors.

Boehringer M, Fischer H, Hennig M, Hunziker D, Huwyler J, Kuhn B, Loeffler BM, Luebbers T, Mattei P, Narquizian R, Sebokova E, Sprecher U, Wessel HP
Bioorg Med Chem Lett 20 1106-8 (2010)
Cited: 13 times
EuropePMC logo PMID: 20031408

Abstract

Synthesis and SAR are described for a structurally distinct class of DPP-IV inhibitors based on aminobenzo[a]quinolizines bearing (hetero-)aromatic substituents in the S1 specificity pocket. The m-(fluoromethyl)-phenyl derivative (S,S,S)-2g possesses the best fit in the S1 pocket. However, (S,S,S)-2i, bearing a more hydrophilic 5-methyl-pyridin-2-yl residue as substituent for the S1 pocket, displays excellent in vivo activity and superior drug-like properties.

Reviews - 3kwj mentioned but not cited (1)

  1. A medicinal chemist's guide to molecular interactions. Bissantz C, Kuhn B, Stahl M. J. Med. Chem. 53 5061-5084 (2010)


Reviews citing this publication (5)

  1. Profound methyl effects in drug discovery and a call for new C-H methylation reactions. Schönherr H, Cernak T. Angew. Chem. Int. Ed. Engl. 52 12256-12267 (2013)
  2. New and unusual scaffolds in medicinal chemistry. Marson CM. Chem Soc Rev 40 5514-5533 (2011)
  3. Recent advances in transition metal-catalyzed Csp(2)-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation. Landelle G, Panossian A, Pazenok S, Vors JP, Leroux FR. Beilstein J Org Chem 9 2476-2536 (2013)
  4. 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)
  5. Recent patents of dipeptidyl peptidase IV inhibitors. Mendieta L, Tarrago T, Giralt E. Expert Opin Ther Pat 21 1693-1741 (2011)

Articles citing this publication (7)

  1. Iron-catalyzed C(sp(2))-H and C(sp(3))-H methylations of amides and anilides. Graczyk K, Haven T, Ackermann L. Chemistry 21 8812-8815 (2015)
  2. Strong nonadditivity as a key structure-activity relationship feature: distinguishing structural changes from assay artifacts. Kramer C, Fuchs JE, Liedl KR. J Chem Inf Model 55 483-494 (2015)
  3. Molecular dynamics and free energy studies of chirality specificity effects on aminobenzo[a]quinolizine inhibitors binding to DPP-IV. Wei C, Desheng L, Jian G, Fang L, Lingling G, Mingjuan J. J Mol Model 19 1167-1177 (2013)
  4. 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)
  5. Fluorinated cyclometalated iridium(iii) complexes as mitochondria-targeted theranostic anticancer agents. Ouyang M, Zeng L, Huang H, Jin C, Liu J, Chen Y, Ji L, Chao H. Dalton Trans 46 6734-6744 (2017)
  6. One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli-Cushman protocol. Pashev A, Burdzhiev N, Stanoeva E. Beilstein J Org Chem 16 1456-1464 (2020)
  7. Structure-Activity Relationship Studies of 4-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-6-imino-N-(naphthalen-2-yl)-1,3,5-triazin-2-amine (FPMINT) Analogues as Inhibitors of Human Equilibrative Nucleoside Transporters. Li R, Mak WW, Li J, Zheng C, Shiu PH, Seto SW, Lee SM, Leung GP. Front Pharmacol 13 837555 (2022)


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