N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-4-chloro-benzamide | 55217-80-6

• 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-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-4-chloro-benzamide
• 英文别名: N-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-4-chlorobenzamide；N-(5-benzylsulfanyl-1,3,4-thiadiazol-2-yl)-4-chlorobenzamide
• CAS: 55217-80-6
• 化学式: C₁₆H₁₂ClN₃OS₂
• 分子量: 361.876
• InChiKey: IGJJUKKHOIAHIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 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：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-4-chloro-benzamide 、 硫酸二甲酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 N-(5-benzylsulfanyl-3-methyl-3H-[1,3,4]thiadiazol-2-ylidene)-4-chloro-benzamide
  参考文献：
  名称：

  Substituted thiadiazolines as inhibitors of central nervous system carbonic anhydrase

  摘要：

  A series (24-30) of substituted thiadiazolines was synthesized and tested for in vitro carbonic anhydrase inhibition and for protective ability against pentylenetetrazole-induced convulsions. ED50 (pentylenetetrazole protection), TD50, and LD50 values are reported for each compound. With the exception of 30, all compounds approximated the model compound methazolamide as in vitro carbonic anhydrase inhibitors. Several of the compounds produced extended protection against pentylenetetrazole-induced convulsions. Ring methoxy substitution in the ortho position appeared to produce maximum activity.

  DOI：

  10.1021/jm00238a005
• 作为产物：
  描述：

  氨基苄巯基噻二唑 、 4-氯苯甲酰氯 在 Amberlite(R) IRA-67 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-4-chloro-benzamide
  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

文献信息

• Substituted thiadiazolines as inhibitors of central nervous system carbonic anhydrase
  作者：James J. Lukes、Karl A. Nieforth

  DOI：10.1021/jm00238a005

  日期：1975.4

  A series (24-30) of substituted thiadiazolines was synthesized and tested for in vitro carbonic anhydrase inhibition and for protective ability against pentylenetetrazole-induced convulsions. ED50 (pentylenetetrazole protection), TD50, and LD50 values are reported for each compound. With the exception of 30, all compounds approximated the model compound methazolamide as in vitro carbonic anhydrase inhibitors. Several of the compounds produced extended protection against pentylenetetrazole-induced convulsions. Ring methoxy substitution in the ortho position appeared to produce maximum activity.
• Discovery and SAR of 1,3,4-thiadiazole derivatives as potent Abl tyrosine kinase inhibitors and cytodifferentiating agents
  作者：Marco Radi、Emmanuele Crespan、Giorgia Botta、Federico Falchi、Giovanni Maga、Fabrizio Manetti、Valentina Corradi、Manuela Mancini、Maria Alessandra Santucci、Silvia Schenone、Maurizio Botta

  DOI：10.1016/j.bmcl.2007.11.112

  日期：2008.2

  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.