3-isopropyl-2-(isopropylimino)thiazolidin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-isopropyl-2-(isopropylimino)thiazolidin-4-one
• 英文别名: 3-isopropyl-2-isopropylimino-thiazolidin-4-one；3-Propan-2-yl-2-propan-2-ylimino-1,3-thiazolidin-4-one
• 化学式: C₉H₁₆N₂OS
• 分子量: 200.305
• InChiKey: NKBHRSJHHWMCFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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-isopropyl-2-(isopropylimino)thiazolidin-4-one 在 盐酸 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 3-Isopropyl-5-(5-nitrofurfuryliden)thiazolidin-2,4-dion
  参考文献：
  名称：

  一系列抗菌活性的5-（5-硝基-2-糠基）噻唑酮，5-（5-硝基-2-糠基丙烯基）噻唑酮和6-（5-硝基-2-呋喃基）的合成及构效关系-4H-1,3-噻嗪酮。

  摘要：

  DOI：

  10.1021/jm00252a008
• 作为产物：
  描述：

  溴乙酸乙酯 、 1,3-二异丙基-2-硫脲 在 tetrabutylammonium tetrafluoroborate 、 magnesium 、 乙腈 作用下， 以63%的产率得到3-isopropyl-2-(isopropylimino)thiazolidin-4-one
  参考文献：
  名称：

  2-imino-1,3-thiazolidin-4-one衍生物的电催化合成及抗菌活性

  摘要：

  摘要 通过在钢栅阴极还原干乙腈获得的电生成的氰基甲基阴离子用于促进溴乙酸乙酯向硫脲衍生物的添加。该反应产生相应的 2-imino-1,3-thiazolidin-4-one。基于通过计算方法获得的动力学和热力学数据讨论了反应途径。此外，还研究了这些新化合物的生物活性。图形概要

  DOI：

  10.1080/17415993.2016.1155588

文献信息

• 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.
• 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
• Electrogenerated base-promoted synthesis and antimicrobial activity of 2-imino-1,3-thiazolidin-4-one derivatives
  作者：Beya Haouas、Taieb Saied、Hanen Ayari、Youssef Arfaoui、Mohamed Lamine Benkhoud、Khaled Boujlel

  DOI：10.1080/17415993.2016.1155588

  日期：2016.7.3

  of dry acetonitrile at a steel grid cathode were used to promote the addition of ethyl bromoacetate to thiourea derivatives. The reaction yields the corresponding 2-imino-1,3-thiazolidin-4-one. The reaction pathway was discussed based on the kinetic and thermodynamic data obtained by computational methods. In addition, the biological activity of these new compounds was also investigated. GRAPHICAL ABSTRACT

  摘要 通过在钢栅阴极还原干乙腈获得的电生成的氰基甲基阴离子用于促进溴乙酸乙酯向硫脲衍生物的添加。该反应产生相应的 2-imino-1,3-thiazolidin-4-one。基于通过计算方法获得的动力学和热力学数据讨论了反应途径。此外，还研究了这些新化合物的生物活性。图形概要