2-(4-methylphenylamino)-5-nitrobenzenesulfonamide | 899790-30-8

• 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: 2-(4-methylphenylamino)-5-nitrobenzenesulfonamide
• 英文别名: 2-(4-Methylanilino)-5-nitrobenzenesulfonamide
• CAS: 899790-30-8
• 化学式: C₁₃H₁₃N₃O₄S
• 分子量: 307.33
• InChiKey: JAPFOGCBNAFZBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 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：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-methylphenylamino)-5-nitrobenzenesulfonamide 在 sodium hydroxide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 0.42h， 生成 N-[2-(4-methylphenylamino)-5-nitrobenzenesulfonyl]-piperidine-1-carboxamide
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Novel Nitrobenzenic Thromboxane Modulators as Antiplatelet Agents Acting on Both the Alpha and Beta Isoforms of the Human Thromboxane Receptor

  摘要：

  Thromboxane A(2) ( TXA(2)) is an arachidonic acid metabolite involved in pathologies such as stroke, myocardial infarction, and atherosclerosis. Consequently, the design of TXA2 receptor ( TP) antagonists remains of great interest in cardiovascular medicine. The actions of TXA2 are mediated by its specific G-protein coupled receptor of which two alternative spliced isoforms, TP alpha and TP beta, have been described in humans. In this study, we report the synthesis of a series of original N-alkyl-N'-[2-( cycloalkyl, alkylaryl)-5-nitrobenzenesulfonyl] urea and N-alkyl-N'-[ 2-( alkylaryl)-5-nitrobenzenesulfonyl]-N"-cyanoguanidines and outline their pharmacological evaluation using the individual TP alpha and TP beta isoforms. Among compounds analyzed, several of them exhibited greater affinity and/or functional activity for either TP alpha or TP beta. The most promising molecules were also found to be antiplatelet agents. From the present results, structural features involved in isoform selectivity can be proposed, and thereby several lead compounds have been identified for the further development of selective TP isoform antagonists.

  DOI：

  10.1021/jm060108a
• 作为产物：
  描述：

  2-氯-5-硝基苯磺酰氯 在 ammonium hydroxide 作用下， 以 various solvent(s) 为溶剂， 生成 2-(4-methylphenylamino)-5-nitrobenzenesulfonamide
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Novel Nitrobenzenic Thromboxane Modulators as Antiplatelet Agents Acting on Both the Alpha and Beta Isoforms of the Human Thromboxane Receptor

  摘要：

  Thromboxane A(2) ( TXA(2)) is an arachidonic acid metabolite involved in pathologies such as stroke, myocardial infarction, and atherosclerosis. Consequently, the design of TXA2 receptor ( TP) antagonists remains of great interest in cardiovascular medicine. The actions of TXA2 are mediated by its specific G-protein coupled receptor of which two alternative spliced isoforms, TP alpha and TP beta, have been described in humans. In this study, we report the synthesis of a series of original N-alkyl-N'-[2-( cycloalkyl, alkylaryl)-5-nitrobenzenesulfonyl] urea and N-alkyl-N'-[ 2-( alkylaryl)-5-nitrobenzenesulfonyl]-N"-cyanoguanidines and outline their pharmacological evaluation using the individual TP alpha and TP beta isoforms. Among compounds analyzed, several of them exhibited greater affinity and/or functional activity for either TP alpha or TP beta. The most promising molecules were also found to be antiplatelet agents. From the present results, structural features involved in isoform selectivity can be proposed, and thereby several lead compounds have been identified for the further development of selective TP isoform antagonists.

  DOI：

  10.1021/jm060108a