5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinone | 16878-94-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinone
• 英文别名: 2-Thiazolidinone, 5-[(2-hydroxyphenyl)methylene]-4-thioxo-；5-[(2-hydroxyphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
• CAS: 16878-94-7
• 化学式: C₁₀H₇NO₂S₂
• 分子量: 237.303
• InChiKey: ORKCFVFHHZRUEZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinone 在 溶剂黄146 、 对苯二酚 作用下， 反应 12.0h， 生成 rel-(6′R,7′R)-7′-(2-hydroxyphenyl)-1-(4-hydroxyphenyl)-3′,7′-dihydro-2H,2′H,5H-spiro[pyrolidin-3,6′-thiopyrano[2,3-d]thiazol]-2,2′,5-trione
  参考文献：
  名称：

  Synthesis and antitrypanosomal activity of new 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles

  摘要：

  A series of novel 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles-based molecules have been synthesized and evaluated as potential antitrypanosomal agents. The most active analogue 3b inhibited Trypanosoma brucei brucei and Trypanosoma brucei gambiense with an IC50 of 0.26 and 0.42 mu M, respectively. They could be considered as potent hits for further antitrypanosomal drug discovery efforts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.091
• 作为产物：
  描述：

  水杨醛 、 4-硫代噻唑烷-2-酮 在 ethylenediamine Tetraacetic Acid 作用下， 以 乙醇 为溶剂， 生成 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinone
  参考文献：
  名称：

  亚芳基丙酮酸基序在通过串联杂-Diels-Alder-半缩醛反应合成新的2H,5H-Chromeno[4',3':4,5]噻唑并[2,3-d]噻唑

  摘要：

  摘要 我们开发了一种使用亚芳基丙酮酸与 5-（邻-羟基苯亚甲基）-取代的 4-硫代-2-噻唑烷酮的串联杂-Diels-Alder-半缩醛反应，产生 6-羟基-2-氧代-5-苯基- 3,5a,6,11b-四氢-2H,5H-色基[4',3':4,5]噻唑并[2,3-d][1,3]噻唑-6-羧酸。环加成的立体化学通过核磁共振谱和单晶 X 射线衍射分析得到证实。图形概要

  DOI：

  10.1080/00397911.2015.1076004

文献信息

• Synthesis of fused thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels–Alder reaction related tandem and domino processes
  作者：Nataliya Zelisko、Dmytro Atamanyuk、Yuri Ostapiuk、Andriy Bryhas、Vasyl Matiychuk、Andrzej Gzella、Roman Lesyk

  DOI：10.1016/j.tet.2015.10.019

  日期：2015.12

  synthesized via hetero-Diels–Alder reaction related acylation-based tandem processes of 5-(ortho-hydroxybenzylidene)-substituted 4-thioxo-2-thiazolidinones with fumaric and maleic acid derivatives. The structurally similar rel-(5aR,5R,11bR) derivatives were synthesized via domino reaction of isorhodanine and (2E)-4-(2-formylphenoxy)but-2-enoates. The stereochemistry of cycloadditions was confirmed by

  各种新颖rel-（5 R， 5 AR， 11点的bS）- 2,6-二氧代-3,5-一个，6,11 b -四氢- 2 Н，5 ħ -chromeno [4'，3'：4,5通过杂-Diels-Alder反应相关的5-（邻羟基苄叉基）取代的4-硫代氧杂-的酰化串联反应合成了] thiopyrano [2,3- d ] [1,3]噻唑-5-羧酸衍生物具有富马酸和马来酸衍生物的2-噻唑烷酮。结构相似的rel-（5 aR，5 R，11 bR）衍生物是通过异二十烷氨酸和（2 E）-4-（2-甲酰基苯氧基）丁-2-烯酸酯的多米诺反应合成的。通过NMR光谱和单晶X射线衍射分析证实了环加成物的立体化学。
• Citraconic acid and its anhydride-based <i>hetero</i>-Diels–Alder reactions in the synthesis of new thiopyrano[2,3-<i>d</i>][1,3]thiazole derivatives
  作者：Nataliya Zelisko、Olexandr Karpenko、Volodymyr Muzychenko、Andrzej Gzella、Roman Lesyk

  DOI：10.1080/00397911.2020.1867868

  日期：——

  5aR,11bS)-5-methyl-2,6-dioxo-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4΄,3΄:4,5]thiopyrano[2,3-d][1,3]thiazole-5-carboxylic acids were synthesized in 63–72% yields via tandem acylation-hetero-Diels–Alder reaction of 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones with citraconic acid and its anhydride. The regio- and stereochemistry of the process was confirmed by NMR spectral data and a single-crystal

  摘要 新型rel-（5 R，5a R，11b S）-5-甲基-2,6-二氧代-3,5a，6,11b-四氢-2H，5H -chromeno [4΄，3΄：4,5]硫代吡喃并[2,3- d ] [1,3]噻唑-5-羧酸通过串联酰化反应合成，产率为63-72％-杂-Diels-5-（2-羟基苄叉）-4-硫代氧杂-Alder反应2-噻唑烷酮与柠康酸及其酸酐。通过NMR光谱数据和单晶X射线衍射分析证实了该方法的区域和立体化学。
• Tandem hetero-Diels–Alder-hemiacetal reaction in the synthesis of new chromeno[4′,3′:4,5]thiopyrano[2,3-<i>d</i>]thiazoles
  作者：Andrii Lozynskyi、Vasyl Matiychuk、Olexandr Karpenko、Andrzej K. Gzella、Roman Lesyk

  DOI：10.1515/hc-2016-0176

  日期：2017.2.1

  Abstract Novel rel-(5aR,6R,11bS)-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-ones were synthesized via tandem hetero-Diels-Alder-hemiacetal reaction of 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones and α,β-unsaturated aldehydes. The stereochemistry of cycloadditions was confirmed by NMR spectra and a single crystal X-ray diffraction analysis.

  摘要 新型rel-(5aR,6R,11bS)-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4',3':4,5]thiopyrano[2,3-d] [1,3] thiazole-2-ones 是通过 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones 和 α,β-不饱和醛的串联杂-Diels-Alder-半缩醛反应合成的。通过核磁共振谱和单晶 X 射线衍射分析证实了环加成的立体化学。
• [EN] THIOXOTHIAZOLIDINONE DERIVATIVES USEFUL AS INHIBITORS OF TDP1<br/>[FR] DÉRIVÉS DE THIOXOTHIAZOLIDINONES UTILES EN TANT QU'INHIBITEURS DE TDP1
  申请人：US HEALTH

  公开号：WO2013055771A1

  公开（公告）日：2013-04-18

  Tdp1 inhibitors of Formula (I) and methods of using those inhibitors to treat cancer are provided in this disclosure. R1 is hydrogen or lower alkyl and G is a substituted phenyl or optionally substituted heteroaryl group. The disclosed Tdp1 inhibitors may be used alone to treat cancer, but may also be used in combination with another active agent, such as camptothecin or a camptothecin analogue.

  本公开提供的是公式（I）的Tdp1抑制剂及其用于治疗癌症的方法。其中，R1为氢或低碳基，G为取代苯基或可选取代的杂环芳基基团。所披露的Tdp1抑制剂可单独用于治疗癌症，也可与另一种活性剂（例如喜树碱或喜树碱类似物）联合使用。
• Application of the 2(5 H )furanone motif in the synthesis of new thiopyrano[2,3- d ]thiazoles via the hetero-Diels–Alder reaction and related tandem processes
  作者：Andrii Lozynskyi、Borys Zimenkovsky、Andriy Karkhut、Svyatoslav Polovkovych、Andrzej K. Gzella、Roman Lesyk

  DOI：10.1016/j.tetlet.2016.06.060

  日期：2016.7

  Novel thiopyrano[2,3-d]thiazole derivatives were synthesized from 5-arylidene-4-thioxo-2-thiazolidinones and 2(5H)furanone in 62–79% yields via hetero-Diels–Alder reactions and related acylation-based tandem processes. The reaction of 5-(4-fluorophenyl)-4-thioxo-2-thiazolidinone with 2(5H)furanone was studied by DFT at the M06-2X/6-31+G(d,p) level. The stereo- and regioselectivities of cycloaddition

  新型的噻吩并[2,3- d ]噻唑衍生物是由5-芳叉基-4-硫代-2-噻唑烷酮和2（5 H）呋喃酮通过杂Diels-Alder反应和相关的酰化反应合成的，产率为62-79％。串联过程。通过DFT在M06-2X / 6-31 + G（d，p）水平上研究了5-（4-氟苯基）-4-硫代氧-2-噻唑烷酮与2（5 H）呋喃酮的反应。环加成反应的立体选择性和区域选择性通过NMR光谱和单晶X射线衍射分析确定。