1026490-44-7

Basic information

• Product Name: (1-Benzyl-pyrrolidin-3-yl)-(5-chloro-2-nitro-phenyl)-amine
• Synonyms: (1-Benzyl-pyrrolidin-3-yl)-(5-chloro-2-nitro-phenyl)-amine
• CAS NO: 1026490-44-7
• Molecular Weight: 331.802
• Mol File: 1026490-44-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1-Benzyl-pyrrolidin-3-yl)-(5-chloro-2-nitro-phenyl)-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Benzyl-pyrrolidin-3-yl)-(5-chloro-2-nitro-phenyl)-amine(1026490-44-7)
• EPA Substance Registry System: (1-Benzyl-pyrrolidin-3-yl)-(5-chloro-2-nitro-phenyl)-amine(1026490-44-7)

Safety Data

• Hazardous Substances Data: 1026490-44-7(Hazardous Substances Data)

Upstream product

• 700-37-8 4-chloro-2-fluoro-nitrobenzene 
• 18471-40-4 1-Benzyl-3-aminopyrrolidine 

Downstream Products

• 181869-99-8 5-(1H-imidazol-1-yl)-2-nitro-N-(1-benzyl-3-pyrrolidinyl)aniline 

Relevant articles and documents

Novel AMPA receptor antagonists: Synthesis and structure-activity relationships of 1-hydroxy-7-(1H-imidazol-1-yl)-6-nitro-2,3(1H,4H)- quinoxalinedione and related compounds

As part of our study of novel antagonists at the α-amino-3-hydroxy-5- methylisoxazole-4-propionate (AMPA) subtype of excitatory amino acid (EAA) receptors and the pharmacophoric requirements of the receptor, we designed and synthesized a series of 1-substituted 6-imidazolyl-7-nitro-, and 7- imidazolyl-6-nitroquinoxalinediones, as well as related compounds, 6a-j, 7, 11a-e, 15, and 17, which are 1- and 4-substituted analogues of 1 (YM90K), and evaluated their activity to inhibit [3H]AMPA binding from rat whole brain. On the basis of their structure-activity relationships (SAR), we deduced that the amide proton of the imidazolyl-near side of the quinoxalinedione nucleus is not essential for AMPA receptor binding, whereas that of the imidazolyl- far amide is. Further, the receptors possess size-limited bulk tolerance for their N-substituents on the imidazolyl-near amide portion. Moreover, we found that introduction of a hydroxyl group at the imidazolyl-near amide portion causes a severalfold improvement in AMPA receptor affinity over unsubstituted derivatives. Among the compounds, 1-hydroxy-7-(1H-imidazol-1-yl)-6-nitro- 2,3(1H,4H)-quinoxalinedione (11a) showed high affinity for AMPA receptor with a K(i) value of 0.021 μM, which is severalfold greater than that of 1 and NBQX (2) (1, K(i) = 0.084 μM; 2, K(i) = 0.060 μM). Compound 11a also showed over 100-fold selectivity for the AMPA receptor than for the N-methy]-D- aspartate (NMDA) receptor and the glycine site on NMDA receptor.