(E)-2-(2-{2-[4-(chloromethyl)thiazol-2-yl]hydrazono}ethyl)isoindoline-1,3-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (E)-2-(2-{2-[4-(chloromethyl)thiazol-2-yl]hydrazono}ethyl)isoindoline-1,3-dione
• 英文别名: 2-[(2E)-2-[[4-(chloromethyl)-1,3-thiazol-2-yl]hydrazinylidene]ethyl]isoindole-1,3-dione
• 化学式: C₁₄H₁₁ClN₄O₂S
• 分子量: 334.786
• InChiKey: NESOUKKWAFURKG-FZSIALSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯二甲酰亚氨基乙醛 在 盐酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (E)-2-(2-{2-[4-(chloromethyl)thiazol-2-yl]hydrazono}ethyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Phthalimido-thiazoles as building blocks and their effects on the growth and morphology of Trypanosoma cruzi

  摘要：

  Chagas disease is a parasitic infection caused by protozoan Trypanosoma cruzi that affects approximately 6-7 million people worldwide. Benznidazole is the only drug approved for treatment during the acute and asymptomatic chronic phases; however, its efficacy during the symptomatic chronic phase is controversial. The present work reports the synthesis and anti-T. cruzi activities of a novel series of phthalimido-thiazoles. Some of these compounds showed potent inhibition of the trypomastigote form of the parasite at low cytotoxicity concentrations in spleen cells, and the resulting structure-activity relationships are discussed. We also showed that phthalimido-thiazoles induced ultrastructural alterations on morphology, flagellum shortening, chromatin condensation, mitochondria swelling, reservosomes alterations and endoplasmic reticulum dilation. Together, these data revealed, for the first time, a novel series of phthalimido-thiazoles-structure-based compounds with potential effects against T. cruzi and lead-like characteristics against Chagas disease. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.01.010

文献信息

• Phthalimido-thiazoles as building blocks and their effects on the growth and morphology of Trypanosoma cruzi
  作者：Paulo André Teixeira de Moraes Gomes、Arsênio Rodrigues Oliveira、Marcos Veríssimo de Oliveira Cardoso、Edna de Farias Santiago、Miria de Oliveira Barbosa、Lucianna Rabelo Pessoa de Siqueira、Diogo Rodrigo Magalhães Moreira、Tanira Matutino Bastos、Fábio André Brayner、Milena Botelho Pereira Soares、Andresa Pereira de Oliveira Mendes、Maria Carolina Accioly Brelaz de Castro、Valéria Rego Alves Pereira、Ana Cristina Lima Leite

  DOI：10.1016/j.ejmech.2016.01.010

  日期：2016.3

  Chagas disease is a parasitic infection caused by protozoan Trypanosoma cruzi that affects approximately 6-7 million people worldwide. Benznidazole is the only drug approved for treatment during the acute and asymptomatic chronic phases; however, its efficacy during the symptomatic chronic phase is controversial. The present work reports the synthesis and anti-T. cruzi activities of a novel series of phthalimido-thiazoles. Some of these compounds showed potent inhibition of the trypomastigote form of the parasite at low cytotoxicity concentrations in spleen cells, and the resulting structure-activity relationships are discussed. We also showed that phthalimido-thiazoles induced ultrastructural alterations on morphology, flagellum shortening, chromatin condensation, mitochondria swelling, reservosomes alterations and endoplasmic reticulum dilation. Together, these data revealed, for the first time, a novel series of phthalimido-thiazoles-structure-based compounds with potential effects against T. cruzi and lead-like characteristics against Chagas disease. (C) 2016 Elsevier Masson SAS. All rights reserved.