So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Donnier-Marechal, Marion; Carato, Pascal; Larchanche, Paul-Emmanuel; Ravez, Severine; Boulahjar, Rajaa; Barczyk, Amelie; Oxombre, Benedicte; Vermersch, Patrick; Melnyk, Patricia researched the compound: 1-(4-Chlorophenyl)pyrrolidin-2-one( cas:7661-33-8 ).Synthetic Route of C10H10ClNO.They published the article 《Synthesis and pharmacological evaluation of benzamide derivatives as potent and selective sigma-1 protein ligands》 about this compound( cas:7661-33-8 ) in European Journal of Medicinal Chemistry. Keywords: aminoalkyl benzamide preparation sigma protein cytotoxicity human docking SAR; benzyl methyl propanamine preparation sigma protein safety human SAR; Benzamide; CNS; Sigma protein. We’ll tell you more about this compound (cas:7661-33-8).
A series of novel N-(aminoalkyl)benzamide derivatives such as I [m = 2, 3; R1 = Me; R2 = Bn, (CH2)2C6H4; R1R2 = (CH2)4, (CH2)2O(CH2)2, (CH2)2NMe(CH2)2, etc.; R3 = H, 4-n-Bu, 4-Cl, etc.] and N-benzyl-N-methyl-propan-1-amine derivatives II [X = CH2NH, SO2NH, NHC(O)] was designed, synthesized and pharmacol. evaluated. In vitro competition binding assays against sigma proteins (sigma-1 S1R and sigma-2 S2R) revealed that most of them conferred S2R/S1R selectivity toward without cytotoxic effects on SY5Y cells, especially with compounds I [m = 2, 3; R1 = Me; R2 = Bn]. Some selected compounds were also evaluated for their agonist and antagonist activities on a panel of 40 receptors and results showed the importance of the nature and the position with halogeno atom on the benzamide scaffold, the length chain and also the contribution of the hydrophobic part on the amine group. Among them, compounds I [m = 2, 3; R1 = Me; R2 = Bn; R3 = 4-Cl, 4-CN, 4-NO2] showed excellent affinity for S1R (Ki = 1.2-3.6 nM), selectivity for S2R (Ki up to 1400 nM) and high selectivity index (IC50(SY5Y)/Ki(S1R) ratio from 28/000 to 83/000). Furthermore, these compounds I and II presented an excellent safety profile over 40 other receptors.
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