3-(2-chlorophenyl)-2-thioxothiazolidin-4-one | 1013919-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-chlorophenyl)-2-thioxothiazolidin-4-one
• 英文别名: 3-(2-chlorophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 1013919-43-1
• 化学式: C₉H₆ClNOS₂
• 分子量: 243.738
• InChiKey: ISHMAWZQMWOQJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-chlorophenyl)-2-thioxothiazolidin-4-one 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 3-(2-Chloro-phenyl)-4-hydroxy-5-{(2-hydroxy-phenyl)-[1H-pyridin-(2E)-ylideneamino]-methyl}-3H-thiazole-2-thione
  参考文献：
  名称：

  Singh, J. S; Khan, M. H.; Tiwari, N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 4, p. 350 - 354

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium 2-(((2-chlorophenyl)carbamothioyl)thio)acetate 在 盐酸 作用下， 以 水 为溶剂， 生成 3-(2-chlorophenyl)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Catalytic dynamic spectrofluorimetry determination of trace antimony using new type arsenoxylphenylazo rhodanine

  摘要：

  A precise, simple, new spectrofluorimetry method is proposed for determination of trace antimony which is based on the reaction between potassium periodate and the new type fluorescent reagent 3-o-chlorophenyl-5-(2'-arsenoxylphenylazo) rhodanine (2ClRAAP). The possible mechanism is proposed. The fluorescence intensity is investigated to be sharply enhanced by the oxidation of 3-o-chlorophenyl-5-(2'-arsenoxylphenylazo) rhodanine by potassium periodate with antimony as catalyst in the buffer medium of potassium hydrogen phthalate-sodium hydroxide (pH 5.2). Under the optimum conditions the great increase of fluorescence intensity has a linear relationship against the concentration of antimony in the range of 0.2-10 mu g L-1 with a detection limit of 1.65 x 10(-10) g mL(-1). This proposed method led to the satisfied determination of antimony in environment water. (C) 2008 Published by Elsevier B.V.

  DOI：

  10.1016/j.saa.2008.06.047

文献信息

• A New Synthesis Strategy for Rhodanine and Its Derivatives
  作者：Zhenliang Pan、Wankai An、Lulu Wu、Liangxin Fan、Guoyu Yang、Cuilian Xu

  DOI：10.1055/a-1485-5925

  日期：2021.7

  Rhodanine and its derivatives have been known as privileged structures in pharmacological research because of their wide spectrum of biological activities, but the synthesis method of rhodanine skeleton is limited. In this paper, not only rhodanine skeleton, but also N-aryl rhodanines can be directly prepared via the reaction of thioureas and thioglycolic acid in one step catalyzed by protic acid,

  罗丹宁及其衍生物由于其广泛的生物活性而在药理学研究中被称为特权结构，但罗丹宁骨架的合成方法受到限制。本文通过质子酸催化硫脲与巯基乙酸的反应，不仅可以直接制备罗丹宁骨架，而且可以直接制备N-芳基罗丹宁，为罗丹宁及其衍生物的合成提供了一种新途径。所开发的策略是简单，高效，原子经济的，并且产率高。
• Design, synthesis and biological evaluation of imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as lymphoid-specific tyrosine phosphatase inhibitors
  作者：Xiao Liang、Huansheng Fu、Peng Xiao、Hao Fang、Xuben Hou

  DOI：10.1016/j.bioorg.2020.104124

  日期：2020.10

  Lymphoid-specific tyrosine phosphatase (LYP), which exclusively exists in immune cells and down-regulates T cell receptor signaling (TCR), has becoming a potent target for various autoimmune diseases. Herein, we designed and synthesized imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as new LYP inhibitors. Among them, the cinnamic acids-based inhibitors (9p and 9r) displayed good

  淋巴特异性酪氨酸磷酸酶（LYP）专门存在于免疫细胞中，并下调T细胞受体信号传导（TCR），已成为各种自身免疫疾病的有效靶标。在本文中，我们设计并合成了咪唑烷-2,4-二酮和2-硫代噻唑烷二-4-酮衍生物作为新的LYP抑制剂。其中，基于肉桂酸的抑制剂（9p和9r）表现出良好的LYP抑制活性（IC 50  = 2.85–6.95μM）。特别是，最有效的抑制剂9r被鉴定为竞争性抑制剂（K i  = 1.09μM），可逆地结合LYP。同时，与已知的LYP抑制剂A15相比，9r对其他磷酸酶的选择性更好。此外，化合物9r可以调节Jurkat T细胞中TCR相关的信号传导途径。
• Novel rhodanines with anticancer activity: design, synthesis and CoMSIA study
  作者：Subhankar P. Mandal、Mithuna Mithuna、Aakriti Garg、Sanjana S. Sahetya、S. R. Nagendra、H. S. Sripad、Mendon Manisha Manjunath、Sitaram Sitaram、Mukesh Soni、R. Nasir Baig、S. Vasanth Kumar、B. R. Prashantha Kumar

  DOI：10.1039/c6ra08785j

  日期：——

  Three different series of some novel N-substituted rhodanines were designed for anticancer activity and prepared from the corresponding dithiocarbamates. The synthesized compounds were analyzed by IR, NMR and MASS to...

  设计了三种不同系列的一些新颖的N-取代的罗丹宁类化合物以用于抗癌活性，并由相应的二硫代氨基甲酸酯制备。通过IR，NMR和MASS对合成的化合物进行分析，以...
• 725. The preparation of some 3-substituted rhodanines and their thiazine analogues
  作者：J. L. Garraway

  DOI：10.1039/jr9610003733

  日期：——
• Axially chiral N-(o-aryl)-2-thioxo-oxazolidine-4-one and rhodanine derivatives: enantiomeric separation and determination of racemization barriers
  作者：Esra Müjde Yılmaz、İlknur Doğan

  DOI：10.1016/j.tetasy.2008.09.001

  日期：2008.9

  Axially chiral 5,5-dimethyl-3-(o-aryl)rhodanine, 3-(o-aryl)rhodanine and 5,5-dimethyl-3-(o-aryl)-2-thioxo-4-oxazolidinone derivatives have been synthesized as racemates and the energy barriers to enantiomerization have been determined by dynamic H-1 NMR or by following the thermal equilibration of the separated enantiomers using chiral HPLC. The barriers to rotation about the N-sp2-C-aryl single bond were found to be 82-129 kJ/mol. The racemization barriers in these compounds are affected by the size of the ortho-substituent on the aryl ring. The magnitude of the barriers was found to change linearly with the van der Waals radii of the ortho-halogen substituents. (C) 2008 Elsevier Ltd. All Fights reserved.