191591-74-9

Basic information

• Product Name: 1-benzyl-5-(3-chloropropyl)-1,4,5,6, 7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione
• Synonyms: 1-benzyl-5-(3-chloropropyl)-1,4,5,6, 7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione
• CAS NO: 191591-74-9
• Molecular Weight: 330.814
• Mol File: 191591-74-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-benzyl-5-(3-chloropropyl)-1,4,5,6, 7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-5-(3-chloropropyl)-1,4,5,6, 7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione(191591-74-9)
• EPA Substance Registry System: 1-benzyl-5-(3-chloropropyl)-1,4,5,6, 7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione(191591-74-9)

Safety Data

• Hazardous Substances Data: 191591-74-9(Hazardous Substances Data)

Upstream product

• 931-03-3 1H-pyrrole-3-carboxylic acid 
• 191591-59-0 3-(3-pyrrolecarboxamido)propionic acid 
• 191591-64-7 6,7-dihydro-1H,5H-pyrrolo[3,2-c]azepine-4,8-dione 
• 191591-55-6 benzyl 3-(3-pyrrolecarboxamido)-propionate 

Downstream Products

• 191591-91-0 1-benzyl-5-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione 

Relevant articles and documents

Synthesis and serotonin 2 (5-HT2) receptor antagonist activity of 5- aminoalkyl-substituted pyrrolo [3,2-c]azepines and related compounds

A series of 5-aminoalkylpyrrolo[3,2,c]azepine derivatives was synthesized and their serotonin 2 (5-HT2) receptor antagonist and antiplatelet aggregation activities were evaluated. 5-HT2 receptor antagonist activity was largely determined by the nature of the substituent at the 8-position as well as the aminoalkyl group at the 5-position of the pyrrolo[3,2-c]azepine ring. Compound 18a, 5-[3-[4-(4-(4- fluorophenyl)piperazin-1-yl]propyl]-8-hydroxy-1-methyl-1,4,5,6,7,8- hexahydropyrrolo[3,2-c]azepin-4-one, was recognized as having potent 5-HT2 receptor antagonist activity with weak α1 adrenoceptor blocking activity and no significant D2 receptor binding affinity, while the corresponding isomeric pyrrolo[3,4-c]azepine derivative (22) displayed only weak 5-HT2 receptor antagonist activity. After racemic 18a was resolved directly via diastereomeric salt formation, each enantiomer was evaluated precisely. The 5-HT2 receptor antagonist activity of 18a was found to reside primarily in (-)-18a (which was about 14-fold more potent than (+)-18a in isolated guinea pig arteries). Consequently, (S)-(-)-18a (SUN C5174)displayed the overall best profile with potent 5-HT2 receptor antagonist activity (pA2 = 8.98 ± 0.06) and high selectivity versus other receptors. SUN C5174 showed a marked inhibitory effect on the platelet aggregation induced by serotonin in combination with collagen and adenosine diphosphate (ADP) in canine or human platelet-rich plasma (IC50 = 6.5 to 16 nM). Moreover, this compound significantly inhibited the mortality rate in mouse acute pulmonary thromboembolitic death induced by collagen and serotonin at oral doses of 0.3 mg/kg or higher. SUN C5174 is currently undergoing clinical evaluation.