N-(5-(4-nitrobenzylthio)-1,3,4-thiadiazol-2-yl)-4-chlorobenzamide | 530126-52-4

• 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-(5-(4-nitrobenzylthio)-1,3,4-thiadiazol-2-yl)-4-chlorobenzamide
• 英文别名: 4-chloro-N-[5-[(4-nitrophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]benzamide
• CAS: 530126-52-4
• 化学式: C₁₆H₁₁ClN₄O₃S₂
• 分子量: 406.873
• InChiKey: WHPAIRPZLHBOIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰氯 、 2-amino-5-[(4-nitrobenzyl)thio]-1,3,4-thiadiazole 在 Amberlite(R) IRA-67 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 N-(5-(4-nitrobenzylthio)-1,3,4-thiadiazol-2-yl)-4-chlorobenzamide
  参考文献：
  名称：

  Discovery and SAR of 1,3,4-thiadiazole derivatives as potent Abl tyrosine kinase inhibitors and cytodifferentiating agents

  摘要：

  A series of substituted benzoylamino-2-[(4-benzyl)thio]-1,3,4-thiadiazoles has been discovered as potent AN tyrosine kinase inhibitors. Molecular docking simulations on the AN tyrosine kinase were conducted in order to rationalize the SAR of the synthesized inhibitors. The most active compound identified from the enzymatic screening (6a) showed interesting inhibitory activity on Imatimb-sensitive murine myeloid 3B clone and Bcr-Abl-independent Imatinib-resistant leukemia cells. Surprisingly, 6a was also proved to act as differentiating inducers in human promyelocytic leukemia cells (HL-60). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.112