191591-55-6

Basic information

• Product Name: benzyl 3-(3-pyrrolecarboxamido)-propionate
• CAS NO: 191591-55-6
• Molecular Weight: 272.304
• Mol File: 191591-55-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: benzyl 3-(3-pyrrolecarboxamido)-propionate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 3-(3-pyrrolecarboxamido)-propionate(191591-55-6)
• EPA Substance Registry System: benzyl 3-(3-pyrrolecarboxamido)-propionate(191591-55-6)

Safety Data

• Hazardous Substances Data: 191591-55-6(Hazardous Substances Data)

Upstream product

• 931-03-3 1H-pyrrole-3-carboxylic acid 
• 27019-47-2 β-alanine benzyl ester p-toluenesulfonate 

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 
• 191591-89-6 1-ethyl-5-[3-[4-(4-fluorophenyl)-piperazin-1-yl]propyl]-1,4,5,6,7,8-hexahydropyrrolo-[3,2-c]azepine-4,8-dione 
• 191591-74-9 1-benzyl-5-(3-chloropropyl)-1,4,5,6, 7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione 
• 191591-68-1 1-benzyl-1,4,5,6,7,8-hexahydropyrrolo-[3,2-c]azepine-4,8-dione 

Relevant articles and documents

Pyrroloazepine compounds

Disclosed are pyrroloazepine compounds and their salts. These pyrroloazepine compounds are represented by formula (I) wherein the dashed line indicates the presence or absence of a bond; and, when the bond is present, Z2is not present and Z1is H but, when the bond is absent, Z1and Z2are both Hs; Z1is H and Z2is OH; Z1and Z2are both SR5s in which R5is alkyl, aralkyl or aryl; or Z1and Z2are combined together to represent O, NOR6in which R6is H, alkyl, aralkyl or aryl, or C2-C3alkylenedithio; R is H, alkyl, cycloalkyl, cycloalkyl alkyl or aralkyl; and the ring P is a specific pyrrole ring. These pyrroloazepine compounds and salts are effective as preventives or therapeutics for general circulatory diseases such as hypertension, heart failure, ischemic hear diseases, cerebrovascular disturbances and peripheral circulatory disturbances. Their production processes are also disclosed

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.