6-chloro-1-(2,4,6-trimethylphenylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one | 1221883-99-3

• 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: 6-chloro-1-(2,4,6-trimethylphenylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one
• 英文别名: 5-chloro-3-(2,4,6-trimethylphenyl)sulfonyl-1H-benzimidazol-2-one
• CAS: 1221883-99-3
• 化学式: C₁₆H₁₅ClN₂O₃S
• 分子量: 350.826
• InChiKey: DTCDDPOBJLMFDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  光气 、 N-(2-amino-5-chlorophenyl)-2,4,6-trimethylbenzenesulfonamide 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 4.0h， 以62%的产率得到6-chloro-1-(2,4,6-trimethylphenylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one
  参考文献：
  名称：

  Novel 1,3-dihydro-benzimidazol-2-ones and their analogues as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

  摘要：

  A series of novel benzimidazolones and their analogues, characterized by the presence of one or more methyl groups or other bioisosteric moieties at different positions of the phenyl ring at N-1, were synthesized and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). Most of the new compounds proved to be highly effective in inhibiting both HIV-1 replication in MT4 cells with minimal cytotoxicity and RT enzyme at nanomolar concentrations. Some derivatives were also tested against RTs containing single amino acid mutations responsible for resistance to non-nucleoside reverse transcriptase inhibitors (NNRTIs). The different potencies displayed by the new compounds were studied using molecular modeling. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.059

文献信息

• Novel 1,3-dihydro-benzimidazol-2-ones and their analogues as potent non-nucleoside HIV-1 reverse transcriptase inhibitors
  作者：Anna-Maria Monforte、Patrizia Logoteta、Laura De Luca、Nunzio Iraci、Stefania Ferro、Giovanni Maga、Erik De Clercq、Christophe Pannecouque、Alba Chimirri

  DOI：10.1016/j.bmc.2009.12.059

  日期：2010.2

  A series of novel benzimidazolones and their analogues, characterized by the presence of one or more methyl groups or other bioisosteric moieties at different positions of the phenyl ring at N-1, were synthesized and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). Most of the new compounds proved to be highly effective in inhibiting both HIV-1 replication in MT4 cells with minimal cytotoxicity and RT enzyme at nanomolar concentrations. Some derivatives were also tested against RTs containing single amino acid mutations responsible for resistance to non-nucleoside reverse transcriptase inhibitors (NNRTIs). The different potencies displayed by the new compounds were studied using molecular modeling. (C) 2010 Elsevier Ltd. All rights reserved.