Indol-adamantyl-carbamate-Cpd42
Highly selective inhibitors of Dipeptidyl Peptidase 9 (DPP9) derived from the clinically used DPP4-Inhibitor vildagliptin. Low nanomolar DPP9 affinity (IC50 DPP9 0.0034+/-0.0006 microM DPP80.6+/-0.2 microM) with DPP9-to-DPP8 selectivity 176 and selectivity >1000 toward all other proline-selective proteases
General
Type : Gliptin, Adamantyl, Carbamate, Indole, Isoindole
Chemical_Nomenclature : (3-((2-(5-fluoroisoindolin-2-yl)-2-oxoethyl)amino)adamantan-1-yl)carbamate || tert-butyl N-[(5R,7S)-3-[[2-(5,6-difluoro-1,3-dihydroisoindol-2-yl)-2-oxoethyl]amino]-1-adamantyl]carbamate
Canonical SMILES : C1C3CC2(CC1(CC(C2)C3)NC(OC(C)(C)C)=O)NCC(=O)N4CC5=C(C4)C=C(C(=C5)F)F || CC(C)(C)OC(=O)NC12C[C@@H]3C[C@H](C1)CC(C3)(C2)NCC(=O)N4CC5=CC(=C(C=C5C4)F)F
InChI : InChI=1S\/C25H33F2N3O3\/c1-23(2,3)33-22(32)29-25-9-15-4-16(10-25)8-24(7-15,14-25)28-11-21(31)30-12-17-5-19(26)20(27)6-18(17)13-30\/h5-6,15-16,28H,4,7-14H2,1-3H3,(H,29,32) || InChI=1S\/C25H33F2N3O3\/c1-23(2,3)33-22(32)29-25-9-15-4-16(10-25)8-24(7-15,14-25)28-11-21(31)30-12-17-5-19(26)20(27)6-18(17)13-30\/h5-6,15-16,28H,4,7-14H2,1-3H3,(H,29,32)\/t15-,16+,24?,25?
InChIKey : PYOHEUZJJMWWMD-UHFFFAOYSA-N || PYOHEUZJJMWWMD-MEYXOBLXSA-N
Other name(s) : DPP9-IN-42 || DPP9 inhibitor 42 || GTPL12942 || GLXC-27647 || compound 42 [PMID: 37721854]
MW : 461.5
Formula : C25H33F2N3O3
CAS_number :
PubChem : 169422746
UniChem : PYOHEUZJJMWWMD-UHFFFAOYSA-N, PYOHEUZJJMWWMD-MEYXOBLXSA-N
Target
Families : Indol-adamantyl-carbamate-Cpd42 ligand of proteins in family
DPP4N_Peptidase_S9
Protein :
human-DPP9
References (2)
| Title : An interdisciplinary approach provides insights into the pronounced selectivity of compound 42 for DPP9 - Beyens_2024_ChemMedChem__e202400700 |
| Author(s) : Beyens O , Corthaut S , Lambeir AM , Van der Veken P , Sterckx YG , De Meester I , De Winter H |
| Ref : ChemMedChem , :e202400700 , 2024 |
| Abstract : |
| PubMedSearch : Beyens_2024_ChemMedChem__e202400700 |
| PubMedID: 39552560 |
| Gene_locus related to this paper: human-DPP8 , human-DPP9 |
| Title : Highly Selective Inhibitors of Dipeptidyl Peptidase 9 (DPP9) Derived from the Clinically Used DPP4-Inhibitor Vildagliptin - Benramdane_2023_J.Med.Chem__ |
| Author(s) : Benramdane S , De Loose J , Filippi N , Espadinha M , Beyens O , Rymenant YV , Dirkx L , Bozdag M , Feijens PB , Augustyns K , Caljon G , De Winter H , De Meester I , Van der Veken P |
| Ref : Journal of Medicinal Chemistry , : , 2023 |
| Abstract : |
| PubMedSearch : Benramdane_2023_J.Med.Chem__ |
| PubMedID: 37721854 |