7-chloro-3-(4-(phenylsulfonyl)piperazin-1-yl)benzo[d]isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 7-chloro-3-(4-(phenylsulfonyl)piperazin-1-yl)benzo[d]isoxazole
• 英文别名: 3-[4-(Benzenesulfonyl)piperazin-1-yl]-7-chloro-1,2-benzoxazole；3-[4-(benzenesulfonyl)piperazin-1-yl]-7-chloro-1,2-benzoxazole
• 化学式: C₁₇H₁₆ClN₃O₃S
• 分子量: 377.851
• InChiKey: MJRNMIIILRZRET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二氯苯甲醛 在 N-氯代丁二酰亚胺 、 盐酸羟胺 、 sodium acetate 、 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 四氯化碳 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.75h， 生成 7-chloro-3-(4-(phenylsulfonyl)piperazin-1-yl)benzo[d]isoxazole
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activity of various 3-(4-(substitutedsulfonyl)piperazin-1-yl)benzo[d]isoxazole derivatives

  摘要：

  In this communication, we synthesized a series of twenty four novel 3-(4-(substitutedsulfonyl)piperazin-1-yl)benzo[d]isoxazole analogues, characterized using various spectroscopic techniques and evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis (MTB) H(37)Rv strain. The titled compounds exhibited Minimum inhibitory concentration (MIC) between 3.125 and >50 mu g/mL. Among the tested compounds, 5c, 6a, 6j and 6p exhibited moderate activity (MIC = 12.5 mu g/mL), while Sa and 61 exhibited good activity (MIC = 6.25 mu g/mL) and 6b (MIC = 3.125 mu g/mL) exhibited very good antitubercular activity. In addition, the analogues 5a, Sc, 6a, 6b, 6i, 6j and 6p were subjected to toxicity studies against mouse macrophage (RAW 264.7) cell lines to analyse the selectivity profile of the newly synthesized compounds and selectivity index of the most active compound was found to be >130 indicating suitability of the compound for further drug development. Structure of 6b was further substantiated through single crystal XRD. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.043