5--rhodanin, 5-Cinnamyliden-rhodanin | 15328-87-7

• 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--rhodanin, 5-Cinnamyliden-rhodanin
• 英文别名: 5-Cinnamylidene-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 15328-87-7
• 化学式: C₁₂H₉NOS₂
• 分子量: 247.342
• InChiKey: FPSVMWLWFSURME-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 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--rhodanin, 5-Cinnamyliden-rhodanin 、 alkaline earth salt of/the/ methylsulfuric acid 生成 5t-phenyl-2-thioxo-pent-4-enoic acid
  参考文献：
  名称：

  Zipser, Monatshefte fur Chemie, 1902, vol. 23, p. 964

  摘要：

  DOI：
• 作为产物：
  描述：

  罗丹宁 、 肉桂醛 在 ammonium acetate 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 5--rhodanin, 5-Cinnamyliden-rhodanin
  参考文献：
  名称：

  取代的苯并[ b ]噻吩-2-羧酸及相关酸的合成方法

  摘要：

  在干燥的四氯化碳中，β-芳基-α-巯基丙烯酸与氯的氧化环化反应可快速生成相应的苯并[ b ]噻吩-2-羧酸。此过程是对先前报告的过程的重大改进。粗β-芳基-α-巯基丙烯酸的纯度可以通过在乙醇中用碘滴定来确定，因此无需使用所计算出的氯气量即可纯化粗中间体，而无需进一步纯化即可将其中间体环化。

  DOI：

  10.1016/0040-4020(69)80021-9

文献信息

• Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones
  作者：Sakshi Shah、Baldev Singh

  DOI：10.1016/j.bmcl.2012.07.049

  日期：2012.9

  An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure. (C) 2012 Elsevier Ltd. All rights reserved.
• Rhodanine-based PRL-3 inhibitors blocked the migration and invasion of metastatic cancer cells
  作者：Garam Min、Su-Kyung Lee、Hye-Nan Kim、Young-Min Han、Rhan-Hee Lee、Dae Gwin Jeong、Dong Cho Han、Byoung-Mog Kwon

  DOI：10.1016/j.bmcl.2013.04.092

  日期：2013.7

  PRL-3, phosphatase of regenerating liver-3, plays a role in cancer progression through its involvement in invasion, migration, metastasis, and angiogenesis. We synthesized rhodanine derivatives, CG-707 and BR-1, which inhibited PRL-3 enzymatic activity with IC50 values of 0.8 mu M and 1.1 mu M, respectively. CG-707 and BR-1 strongly inhibited the migration and invasion of PRL-3 overexpressing colon cancer cells without exhibiting cytotoxicity. The specificity of the inhibitors on PRL-3 phosphatase activity was confirmed by the phosphorylation recovery of known PRL-3 substrates such as ezrin and cytokeratin 8. The compounds selectively inhibited PRL-3 in comparison with other phosphatases, and CG-707 regulated epithelial-to-mesenchymal transition (EMT) marker proteins. The results of the present study reveal that rhodanine is a specific PRL-3 inhibitor and a good lead molecule for obtaining a selective PRL-3 inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.
• Bargellini, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906, vol. <5> 15 I, p. 42
  作者：Bargellini

  DOI：——

  日期：——
• An improved synthesis of substituted benzo[b]thiophen-2-carboxylic acids and related acids
  作者：P.M. Chakrabarti、N.B. Chapman、K. Clarke

  DOI：10.1016/0040-4020(69)80021-9

  日期：1969.1

  The oxidative cyclization of β-Aryl-α-mercaptoacrylic acids with chlorine in dry carbon tetrachloride rapidly gives the corresponding benzo[b]thiophen-2-carboxylic acids in high yield. This process is a considerable improvement on processes previously reported. The purity of the crude β-aryl-α-mercaptoacrylic acids can be determined by titration with iodine in ethanol and thus the crude intermediates

  在干燥的四氯化碳中，β-芳基-α-巯基丙烯酸与氯的氧化环化反应可快速生成相应的苯并[ b ]噻吩-2-羧酸。此过程是对先前报告的过程的重大改进。粗β-芳基-α-巯基丙烯酸的纯度可以通过在乙醇中用碘滴定来确定，因此无需使用所计算出的氯气量即可纯化粗中间体，而无需进一步纯化即可将其中间体环化。
• Zipser, Monatshefte fur Chemie, 1902, vol. 23, p. 964
  作者：Zipser

  DOI：——

  日期：——