(Z)-5-(2'-hydroxybenzylidene)-3-methyl-2-thioxothiazolidin-4-one | 23517-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-5-(2'-hydroxybenzylidene)-3-methyl-2-thioxothiazolidin-4-one
• 英文别名: 3-methyl-5-salicylidene-2-thioxo-thiazolidin-4-one；3-Methyl-5-salicyliden-2-thioxo-thiazolidin-4-on；(5Z)-5-(2-hydroxybenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one；(5Z)-5-[(2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 23517-85-3
• 化学式: C₁₁H₉NO₂S₂
• mdl: MFCD01590650
• 分子量: 251.33
• InChiKey: TZKNKVSXJSTKDZ-TWGQIWQCSA-N

物化性质

• 沸点：
  412.0±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基罗丹宁 、 水杨醛 在 溶剂黄146 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以63%的产率得到(Z)-5-(2'-hydroxybenzylidene)-3-methyl-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2

  摘要：

  The identification, synthesis and evaluation of a series of rhodanine and thiazolidin-2,4-dione derivatives as selective inhibitors of human arylamine N-acetyltransferase 1 and mouse arylamine N-acetyltransferase 2 is described. The most potent inhibitors identified have submicromolar activity and inhibit both the recombinant proteins and human NAT1 in ZR-75 cell lysates in a competitive manner. H-1 NMR studies on purified mouse Nat2 demonstrate that the inhibitors bind within the putative active site of the enzyme. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.032

文献信息

• Ganitkewitsch; Turkewitsch, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 515,516,517,518
  作者：Ganitkewitsch、Turkewitsch

  DOI：——

  日期：——
• Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2
  作者：Angela J. Russell、Isaac M. Westwood、Matthew H.J. Crawford、James Robinson、Akane Kawamura、Christina Redfield、Nicola Laurieri、Edward D. Lowe、Stephen G. Davies、Edith Sim

  DOI：10.1016/j.bmc.2008.11.032

  日期：2009.1

  The identification, synthesis and evaluation of a series of rhodanine and thiazolidin-2,4-dione derivatives as selective inhibitors of human arylamine N-acetyltransferase 1 and mouse arylamine N-acetyltransferase 2 is described. The most potent inhibitors identified have submicromolar activity and inhibit both the recombinant proteins and human NAT1 in ZR-75 cell lysates in a competitive manner. H-1 NMR studies on purified mouse Nat2 demonstrate that the inhibitors bind within the putative active site of the enzyme. (C) 2008 Elsevier Ltd. All rights reserved.