(Z)-2-(5-(2-chlorobenzyliden)-4-oxo-4,5-dihydrothiazol-2-ylamino)-4-methyl-N-tosylpentanamide | 1390675-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-(5-(2-chlorobenzyliden)-4-oxo-4,5-dihydrothiazol-2-ylamino)-4-methyl-N-tosylpentanamide
• 英文别名: (2S)-2-[[(5Z)-5-[(2-chlorophenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]-4-methyl-N-(4-methylphenyl)sulfonylpentanamide
• CAS: 1390675-40-7
• 化学式: C₂₃H₂₄ClN₃O₄S₂
• 分子量: 506.046
• InChiKey: OJBAOSHGUMYVHK-KYYPIKSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-5-(2-chlorobenzylidene)-2-(methylthio)thiazol-4(5H)-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (Z)-2-(5-(2-chlorobenzyliden)-4-oxo-4,5-dihydrothiazol-2-ylamino)-4-methyl-N-tosylpentanamide
  参考文献：
  名称：

  Structure-based design of rhodanine-based acylsulfonamide derivatives as antagonists of the anti-apoptotic Bcl-2 protein

  摘要：

  A series of novel rhodanine-based acylsulfonamide derivatives were designed, synthesized, and evaluated as small-molecule inhibitors of anti-apoptotic Bcl-2 protein. These compounds exhibit potent antiproliferative activity in three human tumor cell lines (Hep G2, PC-3 and B16-F10). Among them, the most potent compounds 10 and 11 bind to Bcl-2 with a K-i of 20 and 25 nM, respectively. Docking studies demonstrated that these two compounds orient similarly at the binding site of Bcl-2, and the calculated binding affinities (Glide XP score) of compound 10 is more negative than that of compound 11. The binding interactions of compounds with high binding affinity to Bcl-2 protein were analyzed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.079

文献信息

• Structure-based design of rhodanine-based acylsulfonamide derivatives as antagonists of the anti-apoptotic Bcl-2 protein
  作者：Huan-qiu Li、Jing Yang、Shuhua Ma、Chunhua Qiao

  DOI：10.1016/j.bmc.2012.05.079

  日期：2012.7

  A series of novel rhodanine-based acylsulfonamide derivatives were designed, synthesized, and evaluated as small-molecule inhibitors of anti-apoptotic Bcl-2 protein. These compounds exhibit potent antiproliferative activity in three human tumor cell lines (Hep G2, PC-3 and B16-F10). Among them, the most potent compounds 10 and 11 bind to Bcl-2 with a K-i of 20 and 25 nM, respectively. Docking studies demonstrated that these two compounds orient similarly at the binding site of Bcl-2, and the calculated binding affinities (Glide XP score) of compound 10 is more negative than that of compound 11. The binding interactions of compounds with high binding affinity to Bcl-2 protein were analyzed. (C) 2012 Elsevier Ltd. All rights reserved.