N,3,4-trihydroxybenzimidoyl chloride | 1111736-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,3,4-trihydroxybenzimidoyl chloride
• 英文别名: N,3,4-trihydroxybenzenecarboximidoyl chloride
• CAS: 1111736-09-4
• 化学式: C₇H₆ClNO₃
• 分子量: 187.583
• InChiKey: OTSHATYZKSUKQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,3,4-trihydroxybenzimidoyl chloride 、 tert-butyl(2-methoxy-5-(1-(3,4,5-trimethoxyphenyl)vinyl)phenoxy)dimethylsilane 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions

  摘要：

  [3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn (OAc)(3) mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 mu M, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 mu M. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.048
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 N-氯代丁二酰亚胺 、 羟胺 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 N,3,4-trihydroxybenzimidoyl chloride
  参考文献：
  名称：

  Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions

  摘要：

  [3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn (OAc)(3) mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 mu M, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 mu M. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.048

文献信息

• Ismail, Tabasum; Shafi, Syed; Singh, Parvinder Pal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 5, p. 740 - 747
  作者：Ismail, Tabasum、Shafi, Syed、Singh, Parvinder Pal、Qazi, Naveed Ahmed、Sawant, Sanghapal D.、Ali, Intzar、Khan, Inshad Ali、Kumar、Qazi, Ghulam Nabi、Alam, M. Sarwar

  DOI：——

  日期：——