phthalimidoacetaldehyde thiosemicarbazone | 103646-88-4

• 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: phthalimidoacetaldehyde thiosemicarbazone
• 英文别名: (E)-2-[2-(1,3-dioxoisoindolin-2-yl)ethylidene]hydrazinecarbothioamide；N-(2-thiosemicarbazono-ethyl)-phthalimide；N-(2-Thiosemicarbazono-aethyl)-phthalimid；2-Phthalimidoethanal thiosemicarbazone；[(E)-2-(1,3-dioxoisoindol-2-yl)ethylideneamino]thiourea
• CAS: 103646-88-4
• 化学式: C₁₁H₁₀N₄O₂S
• 分子量: 262.292
• InChiKey: GZJMVENKMIAXPN-WLRTZDKTSA-N

物化性质

• 熔点：
  221-222 °C
• 沸点：
  453.9±47.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  87.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  phthalimidoacetaldehyde thiosemicarbazone 、 1,3-二氯丙酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以82%的产率得到(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
• 作为产物：
  描述：

  2-<2-(methylsulfinyl)ethyl>-1H-isoindole-1,3(2H)dione 在 sodium acetate 、 溶剂黄146 、 sodium nitrite 作用下， 反应 8.0h， 生成 phthalimidoacetaldehyde thiosemicarbazone
  参考文献：
  名称：

  McCormick, Joan E.; McElbinney, R. Stanley, Journal of Chemical Research, Miniprint, 1981, # 10, p. 3601 - 3641

  摘要：

  DOI：