4-allyl-1-thenylidenethiosemicarbazide | 1434-98-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-allyl-1-thenylidenethiosemicarbazide
• 英文别名: Thiophen-2-carbaldehyd-(4-allyl-thiosemicarbazon)；1-Prop-2-enyl-3-(thiophen-2-ylmethylideneamino)thiourea
• CAS: 1434-98-6
• 化学式: C₉H₁₁N₃S₂
• 分子量: 225.338
• InChiKey: CMWOFFHAOZAYOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-allyl-1-thenylidenethiosemicarbazide 、 1,4-二溴-2,3-丁二酮 以75%的产率得到3,3'-allyl-2,2'-bis[(2-thienyl)methylidenehydrazono]-2,2',3,3'-tetrahydro-4,4'-bisthiazole dihydrobromide
  参考文献：
  名称：

  双噻唑类化合物作为克鲁氏锥虫的磷酸三糖异构酶抑制剂的研究进展。鉴定在体内具有活性的新的非诱变剂

  摘要：

  被忽视的疾病美国锥虫病是拉丁美洲的主要健康问题之一。已经提出了来自该病的病原体克氏锥虫（Tc TIM）的磷酸三糖异构酶作为可药物治疗的靶点。一些双苯并噻唑被描述为该酶的不可逆抑制剂。另一方面，已将新型的具有生物活性的含呋喃的噻唑描述为极好的体内抗克鲁维氏菌剂。这鼓励我们设计和开发新的双噻唑类药物，有可能用作美国锥虫病的药物。双-噻唑5，3,3'-烯丙基-2,2'-双[3-（2-呋喃基）-2- propenylidenehydrazono] -2,2'，3,3'-四氢-4,4'-联噻唑，表现最好体外抗克氏锥虫 谱具有比参比药物Nifurtimox和Benznidazole更高的选择性指数，可对抗寄生虫的a药形式。该衍生物显示边际活性对锝TIM然而双-噻唑14，3-烯丙基-2- [3-（2-呋喃基）-2- propenylidenehydrazono] -3'-苯基-2' - （3-苯基-2-丙二烯二氢偶氮]

  DOI：

  10.1016/j.ejmech.2015.06.018
• 作为产物：
  描述：

  2-噻吩甲醛 、 4-丙烯基硫代氨基脲 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以88%的产率得到4-allyl-1-thenylidenethiosemicarbazide
  参考文献：
  名称：

  5-Nitrofuranes and 5-nitrothiophenes with anti-Trypanosoma cruzi activity and ability to accumulate squalene

  摘要：

  Chagas disease represents a serious public health problem in South America. The first line of treatment is Nifurtimox and Benznidazole which generate toxic effects in treated patients. We have recently shown that a number of 5-nitrofuranes possess activity against Trypanosoma cruzi through oxidative stress and inhibition of parasite ergosterol biosynthesis, specifically at the level of squalene epoxidase. Here, we identify new 5-nitrofuranes and the thia-analogues with excellent effects on the viability of T. cruzi and adequate parasite/mammal selectivity indexes. Analysis of the free sterols from parasite incubated, during 120 h, with the compounds showed that some of them accumulated squalene suggesting the squalene epoxidase activity inhibition of the parasite. Nifurtimox was able to accumulate squalene only at lower incubation times. Due to this fact some derivatives were also tested as antifungal agents. Quantitative structure-activity relationship studies were also performed showing relevant features for further new derivatives design. Taken together, the results obtained in the present work point to a more general effect of 5-nitrofuranes and 5-nitrothiophenes in trypanosomatids, opening potential therapeutic possibilities of them for these infectious diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.013