2-((1-phenoxypropan-2-ylidene)hydrazono)-3-methylthiazolidin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((1-phenoxypropan-2-ylidene)hydrazono)-3-methylthiazolidin-4-one
• 英文别名: (2E)-3-methyl-2-[(E)-1-phenoxypropan-2-ylidenehydrazinylidene]-1,3-thiazolidin-4-one
• 化学式: C₁₃H₁₅N₃O₂S
• 分子量: 277.347
• InChiKey: ANCXTGXEOUBSFR-MRKNTEETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯氧基丙酮 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 18.5h， 生成 2-((1-phenoxypropan-2-ylidene)hydrazono)-3-methylthiazolidin-4-one
  参考文献：
  名称：

  Structural Investigation of Anti-Trypanosoma cruzi 2-Iminothiazolidin-4-ones Allows the Identification of Agents with Efficacy in Infected Mice

  摘要：

  We modified the thiazolidinic ring at positions N3, C4, and C5, yielding compounds 6-24. Compounds with a phenyl at position N3, 15-19, 22-24, exhibited better inhibitory properties for cruzain and against the parasite than 2-iminothiazolidin-4-one S. We were able to identify one high-efficacy trypanocidal compound, 2-minothiazolidin-4-one 18, which inhibited the activity of cruzain and the proliferation of epirnastigotes and was cidal for trypomastigotes but was not toxic for splenocytes. Having located some of the structural determinants of the trypanocidal properties, we subsequently wished to determine if the exchange of the thiazolidine for a thiazole ring leaves the functional properties unaffected. We therefore tested thiazoles 26-45 and observed that they did not inhibit cruzain, but they exhibited trypanocidal effects. Parasite development was severely impaired when treated with 18, thus reinforcing the notion that this class of heterocycles can lead to useful cidal agents for Chagas disease.

  DOI：

  10.1021/jm301518v

文献信息

• Structural Investigation of Anti-<i>Trypanosoma cruzi</i> 2-Iminothiazolidin-4-ones Allows the Identification of Agents with Efficacy in Infected Mice
  作者：Diogo Rodrigo Magalhaes Moreira、Salvana Priscylla Manso Costa、Marcelo Zaldini Hernandes、Marcelo Montenegro Rabello、Gevanio Bezerra de Oliveira Filho、Cristiane Moutinho Lagos de Melo、Lucas Ferreira da Rocha、Carlos Alberto de Simone、Rafaela Salgado Ferreira、Jordana Rodrigues Barbosa Fradico、Cássio Santana Meira、Elisalva Teixeira Guimarães、Rajendra Mohan Srivastava、Valéria Rêgo Alves Pereira、Milena Botelho Pereira Soares、Ana Cristina Lima Leite

  DOI：10.1021/jm301518v

  日期：2012.12.27

  We modified the thiazolidinic ring at positions N3, C4, and C5, yielding compounds 6-24. Compounds with a phenyl at position N3, 15-19, 22-24, exhibited better inhibitory properties for cruzain and against the parasite than 2-iminothiazolidin-4-one S. We were able to identify one high-efficacy trypanocidal compound, 2-minothiazolidin-4-one 18, which inhibited the activity of cruzain and the proliferation of epirnastigotes and was cidal for trypomastigotes but was not toxic for splenocytes. Having located some of the structural determinants of the trypanocidal properties, we subsequently wished to determine if the exchange of the thiazolidine for a thiazole ring leaves the functional properties unaffected. We therefore tested thiazoles 26-45 and observed that they did not inhibit cruzain, but they exhibited trypanocidal effects. Parasite development was severely impaired when treated with 18, thus reinforcing the notion that this class of heterocycles can lead to useful cidal agents for Chagas disease.