5-(4-chlorophenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine | 23517-83-1

• 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: 5-(4-chlorophenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine
• 英文别名: (Z)-5-(4'-chlrobenzylidene)-3-methyl-2-thioxothiazolidin-4-one；5-(4-chloro-benzylidene)-3-methyl-2-thioxo-thiazolidin-4-one；5-(4-Chlor-benzyliden)-3-methyl-2-thioxo-thiazolidin-4-on；5-(4-Chlorobenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one；(5Z)-5-[(4-chlorophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 23517-83-1
• 化学式: C₁₁H₈ClNOS₂
• mdl: MFCD01590659
• 分子量: 269.776
• InChiKey: LBRYJAAWKRWXCV-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine 在 aluminum oxide 、 sodium hydroxide 作用下， 以 solid 为溶剂， 反应 0.08h， 以95%的产率得到3-(4-Chlorophenyl)-2-sulfanylprop-2-enoic acid
  参考文献：
  名称：

  Villemin, Didier; Alloum, Abdelkrim Ben, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 79, # 1,4, p. 33 - 42

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基罗丹宁 、 4-氯苯甲醛 在 amberlyst 26 作用下， 以93 %的产率得到5-(4-chlorophenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine
  参考文献：
  名称：

  使用 Amberlyst 26 作为绿色高效碱催化剂超声加速绕丹宁和羰基化合物的无溶剂缩合反应

  摘要：

  已报道了 Amberlyst 26 催化的各种脂肪醛、环烷酮和苯甲醛与绕丹宁的无溶剂缩合反应。人们发现该催化剂的效率、简单的后处理、简单的回收程序以及高催化剂可回收性而收率多次没有任何显着变化，这些都是令人感兴趣的。此外，超声波照射的急剧加速被认为对于在短时间内以中等至良好的产率有效地形成亚烷基罗丹宁、环亚烷基罗丹宁和亚芳基罗丹宁。

  DOI：

  10.1080/17415993.2023.2173008

文献信息

• Omar, M.T.; Sherif, F.A., Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 5, p. 835 - 842
  作者：Omar, M.T.、Sherif, F.A.

  DOI：——

  日期：——
• Rhodanine Derivatives¹
  作者：Frances C. Brown、Charles K. Bradsher、Sara M. Bond、Marny Potter

  DOI：10.1021/ja01149a510

  日期：1951.5
• SAR and Mode of Action of Novel Non-Nucleoside Inhibitors of Hepatitis C NS5b RNA Polymerase
  作者：Jay P. Powers、Derek E. Piper、Yang Li、Veronica Mayorga、John Anzola、James M. Chen、Juan C. Jaen、Gary Lee、Jinqian Liu、M. Greg Peterson、George R. Tonn、Qiuping Ye、Nigel P. C. Walker、Zhulun Wang

  DOI：10.1021/jm050859x

  日期：2006.2.1

  Novel non-nucleoside inhibitors of the HCV RNA polymerase (NS5b) with sub-micromolar biochemical potency have been identified which are selective for the inhibition of HCV NS5b over other polymerases. The structures of the complexes formed between several of these inhibitors and HCV NS5b were determined by X-ray crystallography, and the inhibitors were found to bind in an allosteric binding site separate from the active site. Structure-activity relationships and structural studies have identified the mechanism of action for compounds in this series, several of which possess drug-like properties, as unique, reversible, covalent inhibitors of HCV NS5b.
• 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.
• Omar, M. T.; Sherif, F. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 10, p. 849 - 851
  作者：Omar, M. T.、Sherif, F. A.

  DOI：——

  日期：——