N-(2-amino-5-chlorophenyl)-4-methylbenzenesulfonamide | 926212-67-1

• 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: N-(2-amino-5-chlorophenyl)-4-methylbenzenesulfonamide
• CAS: 926212-67-1
• 化学式: C₁₃H₁₃ClN₂O₂S
• 分子量: 296.777
• InChiKey: AYKZOCNTNKTBLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  光气 、 N-(2-amino-5-chlorophenyl)-4-methylbenzenesulfonamide 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 4.0h， 以87%的产率得到6-chloro-1-(4-methylphenylsulfonyl)-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
• 作为产物：
  描述：

  对甲苯磺酰氯 在 碳酸氢钠 、 sodium hydrogensulfite 、 sodium sulfite 作用下， 以 水 为溶剂， 反应 23.0h， 生成 N-(2-amino-5-chlorophenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  通过芳基亚磺酸钠或芳基磺酰氯与水中硝基芳烃的反应合成N-芳基磺酰胺的铁基金属有机骨架

  摘要：

  已经公开了新开发的芳基亚磺酸钠或芳基磺酰氯与硝基芳烃的化学选择反应。化学中分别使用无毒的水和可循环使用的铁基金属-有机骨架作为溶剂和催化剂，为产生N-芳基磺酰胺提供了一种有效的方法，该方法广泛存在于生物活性化合物和药物中，使该方法论对合成化学和药物化学都具有吸引力。

  DOI：

  10.1016/j.tetlet.2018.10.032

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.
• Fe-based metal-organic frameworks for the synthesis of N-arylsulfonamides via the reactions of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes in water
  作者：Xinxin Li、Fei Chen、Guo-Ping Lu

  DOI：10.1016/j.tetlet.2018.10.032

  日期：2018.11

  A newly developed chemoselective reaction of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes has been disclosed. The chemistry, in which non-toxic water and recyclable iron-based metal-organic frameworks are employed as the solvent and catalyst, respectively, provides an efficient approach for the generation of N-arylsulfonamides, which are widely present in biologically active compounds

  已经公开了新开发的芳基亚磺酸钠或芳基磺酰氯与硝基芳烃的化学选择反应。化学中分别使用无毒的水和可循环使用的铁基金属-有机骨架作为溶剂和催化剂，为产生N-芳基磺酰胺提供了一种有效的方法，该方法广泛存在于生物活性化合物和药物中，使该方法论对合成化学和药物化学都具有吸引力。