3-methyl-2-phenylimino-thiazolidin-4-one | 63500-82-3

• 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-methyl-2-phenylimino-thiazolidin-4-one
• 英文别名: 3-Methyl-2-phenylimino-thiazolidin-4-on；2-Phenylimino-3-methylthiazolidin-4-on；3-methyl-2-phenylimino-1,3-thiazolidin-4-one
• CAS: 63500-82-3
• 化学式: C₁₀H₁₀N₂OS
• 分子量: 206.268
• InChiKey: SOXGCENCQVQSJB-UHFFFAOYSA-N

物化性质

• 熔点：
  55.5 °C(Solv: pentane (109-66-0))
• 沸点：
  320.7±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-2-phenylimino-thiazolidin-4-one 、 1-(2-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5-[[1-(2-fluorophenyl)-2,5-dimethylpyrrol-3-yl]methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype

  摘要：

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.049
• 作为产物：
  描述：

  氯乙酸乙酯 、 1-甲基-3-苯基硫脲 在 sodium acetate 作用下， 以 乙醇 为溶剂， 生成 3-methyl-2-phenylimino-thiazolidin-4-one
  参考文献：
  名称：

  Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype

  摘要：

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.049

文献信息

• Thiazoline derivatives
  申请人：Hoechst Aktiengesellschaft

  公开号：US04346088A1

  公开（公告）日：1982-08-24

  Thiazoline derivatives of the general formula I ##STR1## wherein R.sup.1 to R.sup.7 have the specified meanings, physiologically acceptable acid addition salts thereof, processes for their preparation, pharmaceutical preparations based on these compounds and their use for acting on the serum lipoprotein spectrum. The invention moreover relates to compounds of the formulae ##STR2## wherein A, R, R.sup.1 to R.sup.7, Y and Z have the specified meanings.

  一般式I的噻唑啉衍生物##STR1##其中R.sup.1至R.sup.7具有指定含义，其生理上可接受的酸盐，其制备方法，基于这些化合物的制药制剂以及它们用于调节血清脂蛋白谱的用途。此外，本发明还涉及以下式子的化合物##STR2##其中A、R、R.sup.1至R.sup.7、Y和Z具有指定的含义。
• Basova, Yu. G.; Ramsh, S. M.; Ginak, A. I., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 10, p. 1940 - 1944
  作者：Basova, Yu. G.、Ramsh, S. M.、Ginak, A. I.

  DOI：——

  日期：——
• Basova, Yu. G.; Ramsh, S. M.; Ginak A. I., Journal of Organic Chemistry USSR (English Translation), 1981, p. 867 - 870
  作者：Basova, Yu. G.、Ramsh, S. M.、Ginak A. I.

  DOI：——

  日期：——
• Dains; Coghill; Tihen, University of Kansas Science Bulletin, 1936, vol. 24, p. 25
  作者：Dains、Coghill、Tihen

  DOI：——

  日期：——
• Ramsh,S.M. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 793 - 796
  作者：Ramsh,S.M. et al.

  DOI：——

  日期：——