Inhibitor Report for: LIR General
Type Cyanide , Piperidine , Imidazole Chemical_Nomenclature 2-[[2-[(3S)-3-aminopiperidin-1-yl]-5-methyl-4,6-dioxopyrrolo[3,4-d]imidazol-3-yl]methyl]benzonitrile Canonical SMILES CN1C(=O)C2=C(C1=O)N(C(=N2)N3CCCC(C3)N)CC4=CC=CC=C4C#N InChI InChI=1S/C19H20N6O2/c1-23-17(26)15-16(18(23)27)25(10-13-6-3-2-5-12(13)9-20)19(22-15)24-8-4-7-14(21)11-24/h2-3,5-6,14H,4,7-8,10-11,21H2,1H3/t14-/m0/s1 InChIKey WVRGIUWTFUXDGX-AWEZNQCLSA-N Other name(s) inhibitor no 7 ; 2-[(3s)-3-Aminopiperidin-1-Yl]-1-(2-Cyanobenzyl)-5-Methyl-4,6-Dioxo-3,4,5,6-Tetrahydropyrrolo[3,4-D]imidazol-1-Ium
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Target
Families | LIR ligand of proteins in family: DPP4N_Peptidase_S9 Stucture | 1 structure : 2I3Z : rat DPP-IV with xanthine mimetic inhibitor no 7 Protein | ratno-dpp4
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LIR
Title: Xanthine mimetics as potent dipeptidyl peptidase IV inhibitorsKurukulasuriya R , Rohde JJ , Szczepankiewicz BG , Basha F , Lai C , Jae HS , Winn M , Stewart KD , Longenecker KL and von Geldern TW <3 more author(s)> Kurukulasuriya R , Rohde JJ , Szczepankiewicz BG , Basha F , Lai C , Jae HS , Winn M , Stewart KD , Longenecker KL , Lubben TW , Ballaron SJ , Sham HL , von Geldern TW (- 3) Ref: Bioorganic & Medicinal Chemistry Lett, 16 :6226, 2006 : PubMed Abstract ESTHER: Kurukulasuriya_2006_Bioorg.Med.Chem.Lett_16_6226 PubMedSearch: Kurukulasuriya 2006 Bioorg.Med.Chem.Lett 16 6226 PubMedID: 17010607 Gene_locus related to this paper: ratno-dpp4 Inhibitor(s) related to this paper: LIR Abstract
A series of xanthine mimetics containing 5,5 and 5,6 heterocycle fused imidazoles were synthesized as dipeptidyl peptidase IV inhibitors. Compound 7 is potent (h-DPPIV K(i)=2nM) and exhibits excellent selectivity and no species specificity against rat and human enzymes. The X-ray structure confirms that the binding mode of 7 to rat DPPIV is similar to the parent xanthines.
