(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-methylsulfanyl-1,3-thiazol-4-one | 1415582-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-methylsulfanyl-1,3-thiazol-4-one
• CAS: 1415582-13-6
• 化学式: C₁₁H₉NO₃S₂
• 分子量: 267.329
• InChiKey: UTSFEJWQOZCJTJ-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,7-二氨基庚烷 、 (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-methylsulfanyl-1,3-thiazol-4-one 以 乙醇 为溶剂， 反应 8.0h， 以79%的产率得到(5Z,5'Z)-2,2'-(heptane-1,7-diyldiimino)bis(5-(3,4-dihydroxybenzylidene)-1,3-thiazol-4(5H)-one)
  参考文献：
  名称：

  Design and synthesis of novel bis-thiazolone derivatives as micromolar CDC25 phosphatase inhibitors: Effect of dimerisation on phosphatase inhibition

  摘要：

  CDC25 phosphatases are involved in deregulated cell cycle progression and tumor development with poor prognosis. Among the most potent CDC25 inhibitors, quinonoid-based derivatives have been extensively studied. Dimerisation of heterocyclic quinones has led to IRC-083864, a bis-quinone compound with increased CDC25B inhibitory activity. Thirty-one bis-thiazolone derivatives were synthesized and assayed for CDC25 inhibitory activity. Most of the dimers displayed enhanced inhibitory activities with micromolar IC50 values lower than that observed for each thiazolone scaffold separately. Moreover, most of these compounds were selective CDC25 inhibitors. Dimer 40 showed an IC50 value of 2.9 mu M and could inhibit CDC25 activity without generating reactive oxygen species which is likely to occur with quinone-based inhibitors. Molecular docking studies suggested that the dimers could bind simultaneously to the active site and the inhibitor binding pocket. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.072
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 哌啶 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-methylsulfanyl-1,3-thiazol-4-one
  参考文献：
  名称：

  Design and synthesis of novel bis-thiazolone derivatives as micromolar CDC25 phosphatase inhibitors: Effect of dimerisation on phosphatase inhibition

  摘要：

  CDC25 phosphatases are involved in deregulated cell cycle progression and tumor development with poor prognosis. Among the most potent CDC25 inhibitors, quinonoid-based derivatives have been extensively studied. Dimerisation of heterocyclic quinones has led to IRC-083864, a bis-quinone compound with increased CDC25B inhibitory activity. Thirty-one bis-thiazolone derivatives were synthesized and assayed for CDC25 inhibitory activity. Most of the dimers displayed enhanced inhibitory activities with micromolar IC50 values lower than that observed for each thiazolone scaffold separately. Moreover, most of these compounds were selective CDC25 inhibitors. Dimer 40 showed an IC50 value of 2.9 mu M and could inhibit CDC25 activity without generating reactive oxygen species which is likely to occur with quinone-based inhibitors. Molecular docking studies suggested that the dimers could bind simultaneously to the active site and the inhibitor binding pocket. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.072

文献信息

• Low molecular weight Myc-Max inhibitors
  申请人：Metallo J. Steven

  公开号：US20070203188A1

  公开（公告）日：2007-08-30

  Compounds and compositions for interfering with the association of Myc and Max are described herein. These compounds and compositions are useful in methods inhibiting growth or proliferation of a cell. Methods of inhibiting growth or proliferation of a cell are provided, comprising contacting the cell with an amount of a compound that interferes with Myc and Max association effective to inhibit growth or proliferation of the cell.

  本文描述了干扰Myc和Max结合的化合物和组合物。这些化合物和组合物在抑制细胞生长或增殖的方法中很有用。本文提供了抑制细胞生长或增殖的方法，包括接触细胞与干扰Myc和Max结合的化合物的有效量，以抑制细胞生长或增殖。
• US7872027B2
  申请人：——

  公开号：US7872027B2

  公开（公告）日：2011-01-18
• Design and synthesis of novel bis-thiazolone derivatives as micromolar CDC25 phosphatase inhibitors: Effect of dimerisation on phosphatase inhibition
  作者：Manal Sarkis、Diem Ngan Tran、Stéphanie Kolb、Maria A. Miteva、Bruno O. Villoutreix、Christiane Garbay、Emmanuelle Braud

  DOI：10.1016/j.bmcl.2012.10.072

  日期：2012.12

  CDC25 phosphatases are involved in deregulated cell cycle progression and tumor development with poor prognosis. Among the most potent CDC25 inhibitors, quinonoid-based derivatives have been extensively studied. Dimerisation of heterocyclic quinones has led to IRC-083864, a bis-quinone compound with increased CDC25B inhibitory activity. Thirty-one bis-thiazolone derivatives were synthesized and assayed for CDC25 inhibitory activity. Most of the dimers displayed enhanced inhibitory activities with micromolar IC50 values lower than that observed for each thiazolone scaffold separately. Moreover, most of these compounds were selective CDC25 inhibitors. Dimer 40 showed an IC50 value of 2.9 mu M and could inhibit CDC25 activity without generating reactive oxygen species which is likely to occur with quinone-based inhibitors. Molecular docking studies suggested that the dimers could bind simultaneously to the active site and the inhibitor binding pocket. (C) 2012 Elsevier Ltd. All rights reserved.