1-(1,3-dioxoisoindolin-2-yl)thiourea

• 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: 1-(1,3-dioxoisoindolin-2-yl)thiourea
• 英文别名: (1,3-Dioxoisoindol-2-yl)thiourea
• 化学式: C₉H₇N₃O₂S
• mdl: MFCD00619725
• 分子量: 221.239
• InChiKey: FHJLOOMVNDQONV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴丙酸 、 1-(1,3-dioxoisoindolin-2-yl)thiourea 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以65%的产率得到(Z)-3-(3-oxobenzo[b]thiophen-2(3H)-ylidene)-1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)indolin-2-one
  参考文献：
  名称：

  邻苯二甲酰亚胺作为免疫调节和抗肿瘤药物原型的发现

  摘要：

  优化的抗癌药：合成了一组功能化的邻苯二甲酰亚胺，并评估了其抗肿瘤活性以及作为细胞因子和一氧化氮分泌的调节剂。将它们的功效与沙利度胺的功效进行了比较，结果，鉴定了一种新的有效的抗癌和免疫调节剂化合物2b。

  DOI：

  10.1002/cmdc.200900525
• 作为产物：
  描述：

  苯酐 、 氨基硫脲 以 溶剂黄146 为溶剂， 以51%的产率得到1-(1,3-dioxoisoindolin-2-yl)thiourea
  参考文献：
  名称：

  N4-邻苯二甲酰亚胺苯基（硫代）氨基脲的合成，抗惊厥和神经毒性评估。

  摘要：

  合成了邻苯二甲酰亚胺药效基团的苯基（硫代）氨基脲衍生物，并对其抗惊厥和神经毒性特性进行了评估。在小鼠中使用腹膜内（ip），最大电击诱发的癫痫发作（MES），皮下戊烯四唑（scPTZ）和皮下士的宁（sc STY）诱发的癫痫发作阈值测试进行了初始抗惊厥筛选。化合物2c在所有三个屏幕中均提供了保护。除1d，2a和2d外的化合物在300 mg / kg以下均无神经毒性。发现化合物1a，1b，2c，2d，2g和2i具有口服MES活性。该化合物表现出中枢神经系统抑制和行为绝望的副作用，比常规的抗癫痫药要小。

  DOI：

  10.1016/j.ejps.2003.08.002

文献信息

• Synthesis and anticonvulsant and neurotoxicity evaluation of N4-phthalimido phenyl (thio) semicarbazides
  作者：P Yogeeswari、D Sriram、V Saraswat、J.Vaigunda Ragavendran、M.Mohan Kumar、S Murugesan、R Thirumurugan、J.P Stables

  DOI：10.1016/j.ejps.2003.08.002

  日期：2003.11

  The phenyl (thio) semicarbazide derivatives of phthalimido pharmacophore were synthesized and evaluated for their anticonvulsant and neurotoxic properties. Initial anticonvulsant screening was performed using intraperitoneal (i.p.), maximal electroshock-induced seizure (MES), subcutaneous pentylenetetrazole (scPTZ) and subcutaneous strychnine (sc STY)-induced seizure threshold tests in mice. Compound

  合成了邻苯二甲酰亚胺药效基团的苯基（硫代）氨基脲衍生物，并对其抗惊厥和神经毒性特性进行了评估。在小鼠中使用腹膜内（ip），最大电击诱发的癫痫发作（MES），皮下戊烯四唑（scPTZ）和皮下士的宁（sc STY）诱发的癫痫发作阈值测试进行了初始抗惊厥筛选。化合物2c在所有三个屏幕中均提供了保护。除1d，2a和2d外的化合物在300 mg / kg以下均无神经毒性。发现化合物1a，1b，2c，2d，2g和2i具有口服MES活性。该化合物表现出中枢神经系统抑制和行为绝望的副作用，比常规的抗癫痫药要小。
• Discovery of Phthalimides as Immunomodulatory and Antitumor Drug Prototypes
  作者：Claudia Pessoa、Paulo Michel P. Ferreira、Letícia Veras C. Lotufo、Manoel O. de Moraes、Suellen M. T. Cavalcanti、Lucas Cunha D. Coêlho、Marcelo Z. Hernandes、Ana Cristina L. Leite、Carlos A. De Simone、Vlaudia M. A. Costa、Valdênia M. O. Souza

  DOI：10.1002/cmdc.200900525

  日期：2010.4.6

  Optimized anticancer agents: A set of functionalized phthalimides was synthesized and evaluated for antitumor activities and as modulators of the secretion of cytokines and nitric oxide. Their potency was compared with that of thalidomide, and as a result, a new potent anticancer and immunomodulatory agent, compound 2 b, was identified.

  优化的抗癌药：合成了一组功能化的邻苯二甲酰亚胺，并评估了其抗肿瘤活性以及作为细胞因子和一氧化氮分泌的调节剂。将它们的功效与沙利度胺的功效进行了比较，结果，鉴定了一种新的有效的抗癌和免疫调节剂化合物2b。
• 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.