178327-71-4

Basic information

• Product Name: 2-Pyrrolidinecarboxamide, 5-oxo-N-(phenylmethyl)-, (R)-
• CAS NO: 178327-71-4
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• Mol File: 178327-71-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Pyrrolidinecarboxamide, 5-oxo-N-(phenylmethyl)-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinecarboxamide, 5-oxo-N-(phenylmethyl)-, (R)-(178327-71-4)
• EPA Substance Registry System: 2-Pyrrolidinecarboxamide, 5-oxo-N-(phenylmethyl)-, (R)-(178327-71-4)

Safety Data

• Hazardous Substances Data: 178327-71-4(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 4042-36-8 D-pyrrolidone-5-carboxylic acid 

Downstream Products

• 117659-52-6 1-phenyl-N-[(2R)-pyrrolidin-2-ylmethyl]methanamine 
• 1266228-97-0 methyl (3S,8aR)-2-benzyloctahydropyrrolo[1,2-a]pyrazine-3-carboxylate 
• 1266228-99-2 methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate 
• 1266229-00-8 (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid 
• 1266231-73-5 C₃₃H₅₁N₅O₅ 
• 1266229-12-2 tert-buty l[(1S)-2-({(1S)-1-cyclohexyl-2-oxo-2-[(3S,8aR)-3-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]ethyl}amino)-1-methyl-2-oxoethyl]methylcarbamate 
• 1266230-01-6 tert-butyl [(1S)-2-({(1S)-1-cyclohexyl-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-cromen-4-ylcarbamoyl] hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxoethyl}amino)-1-methyl-2-oxoethyl]methylcarbamate 
• 1266231-92-8 C₃₅H₅₁F₂N₅O₅ 
• 1266232-21-6 C₃₅H₅₁N₅O₆ 
• 1266229-67-7 benzyl {(1S)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-phenylethyl}carbamate 
• 1266230-12-9 benzyl {(1S)-1-(4,4-difluorocyclohexyl)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxoethyl}carbamate 
• 1266230-03-8 benzyl [(1S)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethyl]carbamate 
• 1266229-75-7 (3S,8aR)-2-[(2S)-2-amino-2-phenylacetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide 
• 1266230-13-0 (3S,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide 

Relevant articles and documents

Design and synthesis of potent inhibitor of apoptosis (IAP) proteins antagonists bearing an octahydropyrrolo[1,2-a]pyrazine scaffold as a novel proline mimetic

To develop novel inhibitor of apoptosis (IAP) proteins antagonists, we designed a bicyclic octahydropyrrolo[1,2-a]pyrazine scaffold as a novel proline bioisostere. This design was based on the X-ray co-crystal structure of four N-terminal amino acid residues (AVPI) of the second mitochondria-derived activator of caspase (Smac) with the X-chromosome-linked IAP (XIAP) protein. Lead optimization of this scaffold to improve oral absorption yielded compound 45, which showed potent cellular IAP1 (cIAP1 IC50: 1.3 nM) and XIAP (IC50: 200 nM) inhibitory activity, in addition to potent tumor growth inhibitory activity (GI50: 1.8 nM) in MDA-MB-231 breast cancer cells. X-ray crystallographic analysis of compound 45 bound to XIAP and to cIAP1 was achieved, revealing the various key interactions that contribute to the higher cIAPI affinity of compound 45 over XIAP. Because of its potent IAP inhibitory activities, compound 45 (T-3256336) caused tumor regression in a MDA-MB-231 tumor xenograft model (T/C: -53% at 30 mg/kg).

Heterocyclic Compound

The present invention provides a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof. The compound of the present invention shows a strong IAP antagonistic activity.