2-methylamino-4-thiazolinone | 16312-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-methylamino-4-thiazolinone
• 英文别名: 2-Methyl-amino-thiazolinon-(4)；4(5H)-Thiazolone, 2-(methylamino)-；2-methylimino-1,3-thiazolidin-4-one
• CAS: 16312-19-9
• 化学式: C₄H₆N₂OS
• mdl: MFCD13184172
• 分子量: 130.17
• InChiKey: DDHGVUYPMIUDTI-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C
• 沸点：
  212.0±23.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methylamino-4-thiazolinone 、 喹啉-6-甲醛 在 哌啶 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 2-methylamino-5-[1-quinolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one
  参考文献：
  名称：

  Synthesis and activity of quinolinyl-methylene-thiazolinones as potent and selective cyclin-dependent kinase 1 inhibitors

  摘要：

  A novel series of quinolinyl-methylene-thiazolinones has been identified as potent and selective cyclin-dependent kinase I (CDK1) inhibitors. Their synthesis and structure activity relationships (SAR) are described. Representative compounds from this class reversibly inhibit CDK1 activity in vitro, and block cell cycle progression in human tumor cell lines, suggesting a potential use as antitumor agents. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.081
• 作为产物：
  描述：

  N-甲硫脲 、 氯乙酸 在 sodium acetate 作用下， 以 水 为溶剂， 反应 0.75h， 以71%的产率得到2-methylamino-4-thiazolinone
  参考文献：
  名称：

  SO₂F₂-Mediated N-Alkylation of Imino-Thiazolidinones

  摘要：

  DOI：

  10.1021/acs.joc.1c01247

文献信息

• NMR spectral study of the structure of 2-amino-4-thiazolinones
  作者：S. M. Ramsh、N. A. Smorygo、E. S. Khrabrova、A. I. Ginak

  DOI：10.1007/bf00542789

  日期：1986.4
• Andreasch, Monatshefte fur Chemie, 1885, vol. 6, p. 831
  作者：Andreasch

  DOI：——

  日期：——
• Synthesis and structure-activity relations of a series of antibacterially active 5-(5-nitro-2-furfurylidene)thiazolones, 5-(5-nitro-2-furylpropenylidene)thiazolones, and 6-(5-nitro-2-furyl)-4H-1,3-thiazinones
  作者：Eva B. Akerblom

  DOI：10.1021/jm00252a008

  日期：1974.6
• Methylation of 2-amino-?2-thiazolin-4-one
  作者：Yu. G. Basova、S. M. Ramsh、A. I. Ginak

  DOI：10.1007/bf00503655

  日期：1981.8
• 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
  作者：Mariangela Urbano、Miguel Guerrero、Subash Velaparthi、Melissa Crisp、Peter Chase、Peter Hodder、Marie-Therese Schaeffer、Steven Brown、Hugh Rosen、Edward Roberts

  DOI：10.1016/j.bmcl.2011.09.049

  日期：2011.11

  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.