5-((Z)-4-hydroxybenzylidene)-2-methylmercapto-4-thiazolidinone | 521973-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-((Z)-4-hydroxybenzylidene)-2-methylmercapto-4-thiazolidinone
• 英文别名: (Z)-5-(4-hydroxybenzylidene)-2-(methylthio)thiazol-4(5H)-one；(5Z)-5-[(4-hydroxyphenyl)methylidene]-2-methylsulfanyl-1,3-thiazol-4-one
• CAS: 521973-02-4
• 化学式: C₁₁H₉NO₂S₂
• 分子量: 251.33
• InChiKey: JHFVKLINWAURHV-TWGQIWQCSA-N

物化性质

• 沸点：
  438.4±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 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：
  100
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-((Z)-4-hydroxybenzylidene)-2-methylmercapto-4-thiazolidinone 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]ethyl}-1H-1,2,3-triazol-1-yl)propyl]amino}-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：

  对羟基苯甲醛 在 sodium acetate 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.35h， 生成 5-((Z)-4-hydroxybenzylidene)-2-methylmercapto-4-thiazolidinone
  参考文献：
  名称：

  利用微波辐射和常规方法轻松合成（Z）-5-（取代）-2-（甲硫基）噻唑-4（5 H）-

  摘要：

  一种新的有效合成一些新的（Z）-5-（取代）-2-硫代噻唑啉酮-4-one 3a - 1和（Z）-5-（取代）-2-（甲硫基）噻唑-4（据报道，在微波辐射以及常规条件下，5 H）-1 5a - l。

  DOI：

  10.1016/j.tetlet.2013.12.113

文献信息

• A convenient synthesis of 2-Arylidene-5<i>H</i>-thiazolo[2,3-<i>b</i>]quinazo-line-3,5[2<i>H</i>]-diones and their benzoquinazoline derivatives
  作者：Ahmed I. Khodair

  DOI：10.1002/jhet.5570390607

  日期：2002.11

  Various 5H-thiazolo[2,3-b]quinazoline-3,5[2H]-diones (7a,b), 2-arylidene-5H-thiazolo[2,3–b]quin-azoline-3,5[2H]-diones (9a-o) and 2-arylidene-5H-thiazolo[2,3-b]benzoquinazoline-3,5[2H]-diones (12a,b) have been synthesized via simple and efficient methods.

  各种5 H-噻唑并[2,3- b ]喹唑啉-3,5 [2 H ]-二酮（7a，b），2-亚芳基-5 H-噻唑并[2,3 - b ]喹唑啉-3，通过简单和简单的方法合成了5 [2 H ]-二酮（9a-o）和2-芳叉基5 H-噻唑并[2,3 - b ]苯并喹唑啉-3,5 [2 H ]-二酮（12a，b）。有效的方法。
• Jadhav, Santosh A.; Shioorkar, Mahesh. G.; Chavan, Omprakash S., Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 201 - 207
  作者：Jadhav, Santosh A.、Shioorkar, Mahesh. G.、Chavan, Omprakash S.、Sarkate, Aniket P.、Farooqui, Mazahar、Shinde, Devanand. B.、Pardeshi, Rajendra K.

  DOI：——

  日期：——
• FLUOROGEN ACTIVATING AND SHIFTING TAG (FAST)
  申请人：Paris Sciences et Lettres - Quartier Latin

  公开号：EP3164411B1

  公开（公告）日：2019-08-28
• [EN] FLUOROGEN ACTIVATING AND SHIFTING TAG (FAST)<br/>[FR] ÉTIQUETTE D'ACTIVATION ET DE DÉCALAGE DU SPECTRE D'UN FLUOROGÈNE (FAST)
  申请人：PARIS SCIENCES LETTRES QUARTIER LATIN

  公开号：WO2016001437A2

  公开（公告）日：2016-01-07

  The present invention relates to a functional derivative of a Photoactive Yellow Protein (PYP), or a functional fragment thereof, for fluorescently labelling particles, e.g. proteins, or surfaces, which is capable of binding reversibly a fluorogenic chromophore of formula (I), and which is capable of enhancing the brightness of the said fluorogenic chromophore upon complexation thereto; and of inducing the spectral shift of the said fluorogenic chromophore through the ionization of an auxochromic group thereof.
• 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.