(2S)-N-benzyl-2-[(2S)-2-(2-hydroxyacetyl)pyrrolidine-1-carbonyl]pyrrolidine-1-carboxamide


CAS No. : 162203-65-8

(2S)-N-benzyl-2-[(2S)-2-(2-hydroxyacetyl)pyrrolidine-1-carbonyl]pyrrolidine-1-carboxamide,162203-65-8
Product Details
Cat No:M037391
Molecular Formula:C19H25N3O4
Molecular Weight:359.426
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Appearance:Solid powder
Purity: > 98%
Cat No:M037391
Cas No:162203-65-8
Product-Name:(2S)-N-benzyl-2-[(2S)-2-(2-hydroxyacetyl)pyrrolidine-1-carbonyl]pyrrolidine-1-carboxamide
IUPAC Name:(2S)-N-benzyl-2-[(2S)-2-(2-hydroxyacetyl)pyrrolidine-1-carbonyl]pyrrolidine-1-carboxamide
InChI:InChI=1S/C19H25N3O4/c23-13-17(24)15-8-4-10-21(15)18(25)16-9-5-11-22(16)19(26)20-12-14-6-2-1-3-7-14/h1-3,6-7,15-16,23H,4-5,8-13H2,(H,20,26)/t15-,16-/m0/s1
InChIKey:ICULFJDHZQTNRB-HOTGVXAUSA-N
SMILES:C1CC(N(C1)C(=O)C2CCCN2C(=O)NCC3=CC=CC=C3)C(=O)CO
JTP-4819 is a potent and selective prolyl endopeptidase (PEP) inhibitor with potential for treating Alzheimer/'s disease. At nanomolar concentration, JTP-4819 inhibited the degradation of substance P, arginine-vasopressin, and thyrotropin-releasing hormone by PEP in supernatants of the rat cerebral cortex and hippocampus. Repeated administration of JTP-4819 reversed the aging-induced decrease in brain substance P-like and thyrotropin-releasing hormone-like immunoreactivity, suggesting that this drug may be able to improve the imbalance of peptidergic neuronal systems that develops with senescense by inhibiting PEP activity. JTP-4819 increased acetylcholine release from the frontal cortex and hippocampus, regions closely associated with memory, in both young and aged rats.

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8: Venäläinen JI, Juvonen RO, Forsberg MM, Garcia-Horsman A, Poso A, Wallen EA, Gynther J, Männistö PT. Substrate-dependent, non-hyperbolic kinetics of pig brain prolyl oligopeptidase and its tight binding inhibition by JTP-4819. Biochem Pharmacol. 2002 Aug 1;64(3):463-71. PubMed PMID: 12147298.
9: Wallén EA, Christiaans JA, Saario SM, Forsberg MM, Venäläinen JI, Paso HM, Männistö PT, Gynther J. 4-Phenylbutanoyl-2(S)-acylpyrrolidines and 4-phenylbutanoyl-L-prolyl-2(S)-acylpyrrolidines as prolyl oligopeptidase inhibitors. Bioorg Med Chem. 2002 Jul;10(7):2199-206. PubMed PMID: 11983517.
10: Shinoda M, Miyazaki A, Toide K. Effect of a novel prolyl endopeptidase inhibitor, JTP-4819, on spatial memory and on cholinergic and peptidergic neurons in rats with ibotenate-induced lesions of the nucleus basalis magnocellularis. Behav Brain Res. 1999 Feb 15;99(1):17-25. PubMed PMID: 10512568.
11: Toide K, Shinoda M, Miyazaki A. A novel prolyl endopeptidase inhibitor, JTP-4819--its behavioral and neurochemical properties for the treatment of Alzheimer/'s disease. Rev Neurosci. 1998;9(1):17-29. Review. PubMed PMID: 9683325.
12: Miyazaki A, Toide K, Sasaki Y, Ichitani Y, Iwasaki T. Effect of a prolyl endopeptidase inhibitor, JTP-4819, on radial maze performance in hippocampal-lesioned rats. Pharmacol Biochem Behav. 1998 Feb;59(2):361-8. PubMed PMID: 9476982.
13: Shinoda M, Toide K, Ohsawa I, Kohsaka S. Specific inhibitor for prolyl endopeptidase suppresses the generation of amyloid beta protein in NG108-15 cells. Biochem Biophys Res Commun. 1997 Jun 27;235(3):641-5. PubMed PMID: 9207212.
14: Umemura K, Kondo K, Ikeda Y, Kobayashi T, Urata Y, Nakashima M. Pharmacokinetics and safety of JTP-4819, a novel specific orally active prolyl endopeptidase inhibitor, in healthy male volunteers. Br J Clin Pharmacol. 1997 Jun;43(6):613-8. PubMed PMID: 9205821; PubMed Central PMCID: PMC2042786.
15: Toide K, Shinoda M, Fujiwara T, Iwamoto Y. Effect of a novel prolyl endopeptidase inhibitor, JTP-4819, on spatial memory and central cholinergic neurons in aged rats. Pharmacol Biochem Behav. 1997 Mar;56(3):427-34. PubMed PMID: 9077579.
16: Toide K, Shinoda M, Iwamoto Y, Fujiwara T, Okamiya K, Uemura A. A novel prolyl endopeptidase inhibitor, JTP-4819, with potential for treating Alzheimer/'s disease. Behav Brain Res. 1997 Feb;83(1-2):147-51. PubMed PMID: 9062674.
17: Shinoda M, Matsuo A, Toide K. Pharmacological studies of a novel prolyl endopeptidase inhibitor, JTP-4819, in rats with middle cerebral artery occlusion. Eur J Pharmacol. 1996 Jun 3;305(1-3):31-8. PubMed PMID: 8813528.
18: Toide K, Fujiwara T, Iwamoto Y, Shinoda M, Okamiya K, Kato T. Effect of a novel prolyl endopeptidase inhibitor, JTP-4819, on neuropeptide metabolism in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1996 Feb;353(3):355-62. PubMed PMID: 8692293.
19: Shinoda M, Okamiya K, Toide K. Effect of a novel prolyl endopeptidase inhibitor, JTP-4819, on thyrotropin-releasing hormone-like immunoreactivity in the cerebral cortex and hippocampus of aged rats. Jpn J Pharmacol. 1995 Nov;69(3):273-6. PubMed PMID: 8699636.
20: Toide K, Iwamoto Y, Fujiwara T, Abe H. JTP-4819: a novel prolyl endopeptidase inhibitor with potential as a cognitive enhancer. J Pharmacol Exp Ther. 1995 Sep;274(3):1370-8. PubMed PMID: 7562510.

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