4-fluoro-N-[4-(1-pyrrolidinylsulfonyl)phenyl]benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-fluoro-N-[4-(1-pyrrolidinylsulfonyl)phenyl]benzamide
• 英文别名: 4-fluoro-N-(4-pyrrolidin-1-ylsulfonylphenyl)benzamide
• 化学式: C₁₇H₁₇FN₂O₃S
• 分子量: 348.398
• InChiKey: ZNWHTBSQIGSUBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(吡咯烷-1-磺酰基)-苯胺 、 对氟苯甲酰氯 生成 4-fluoro-N-[4-(1-pyrrolidinylsulfonyl)phenyl]benzamide
  参考文献：
  名称：

  Non-nucleoside inhibitors of the measles virus RNA-dependent RNA polymerase complex activity: Synthesis and in vitro evaluation

  摘要：

  High-throughput screening has identified l-methyl-3-(trifluoromethyl)-N-[4-(pyrrolidinylsulfonyl)phenyl]-1H-pyrazole-5-carboxamide 16677 as a novel and potent (IC50 = 35-145 nM) inhibitor against multiple primary isolates of diverse measles virus (MV) genotypes currently Circulating worldwide. The synthesis of 16677 and several analogs together with effects on MV replication is described. The most potent analog displays nanomolar inhibition against the MV and a selectivity ratio (CC50/IC50) of ca. 16,500. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.06.084

文献信息

• Potent Non-Nucleoside Inhibitors of the Measles Virus RNA-Dependent RNA Polymerase Complex
  作者：Aiming Sun、Jeong-Joong Yoon、Yan Yin、Andrew Prussia、Yutao Yang、Jaeki Min、Richard K. Plemper、James P. Snyder

  DOI：10.1021/jm701239a

  日期：2008.7

  Measles virus (MV) is one of the most infectious pathogens known. In spite of the existence of a vaccine, approximately 350000 deaths/year result from MV or associated complications. Antimeasles compounds Could conceivably diminish these statistics and provide a therapy that complements vaccine treatment. We recently described a high-throughput screening hit compound 1 (16677) against MV-infected cells with the capacity to eliminate viral reproduction at 250 nM by inhibiting the action of the virus's RNA-dependent RNA polymerase complex (RdRp). The compound, 1-methyl-3-(trifluoroi-nethyl)-N-[4-sulfonylphenyl]-1H-pyrazole-5-carboxamide, 1 carries a critical CF3 moiety on the 1,2-pyrazole ring. Elaborating on the preliminary structure-activity (SAR) study, the present work presents the synthesis and SAR of a much broader range of low nanomolar nonpeptidic MV inhibitors and speculates on the role of the CF3 functionality.
• Non-nucleoside inhibitors of the measles virus RNA-dependent RNA polymerase complex activity: Synthesis and in vitro evaluation
  作者：Aiming Sun、Nizal Chandrakumar、Jeong-Joong Yoon、Richard K. Plemper、James P. Snyder

  DOI：10.1016/j.bmcl.2007.06.084

  日期：2007.9

  High-throughput screening has identified l-methyl-3-(trifluoromethyl)-N-[4-(pyrrolidinylsulfonyl)phenyl]-1H-pyrazole-5-carboxamide 16677 as a novel and potent (IC50 = 35-145 nM) inhibitor against multiple primary isolates of diverse measles virus (MV) genotypes currently Circulating worldwide. The synthesis of 16677 and several analogs together with effects on MV replication is described. The most potent analog displays nanomolar inhibition against the MV and a selectivity ratio (CC50/IC50) of ca. 16,500. Published by Elsevier Ltd.