5-(4-chlorophenyl)-2-furancarboxyaldehyde thio semicarbazone | 60698-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-chlorophenyl)-2-furancarboxyaldehyde thio semicarbazone
• 英文别名: 5-(4-chloro-phenyl)-furan-2-carbaldehyde thiosemicarbazone；5-(4-Chlor-phenyl)-furan-2-carbaldehyd-thiosemicarbazon；Hydrazinecarbothioamide, 2-[[5-(4-chlorophenyl)-2-furanyl]methylene]-；[[5-(4-chlorophenyl)furan-2-yl]methylideneamino]thiourea
• CAS: 60698-40-0
• 化学式: C₁₂H₁₀ClN₃OS
• mdl: MFCD00695933
• 分子量: 279.75
• InChiKey: OYEQJQNRMFKNDG-UHFFFAOYSA-N

物化性质

• 沸点：
  448.8±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-2-furancarboxyaldehyde thio semicarbazone 、 4-bromoacetyl-3-(4-methoxyphenyl)sydnone 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 以49%的产率得到4-[2-[2-[[5-(4-chlorophenyl)furan-2-yl]methylidene]hydrazinyl]-1,3-thiazol-4-yl]-3-(4-methoxyphenyl)oxadiazol-3-ium-5-olate
  参考文献：
  名称：

  Kalluraya, Balakrishna; Vishwanatha; Rahiman, Revue Roumaine de Chimie, 2000, vol. 45, # 1, p. 71 - 75

  摘要：

  DOI：
• 作为产物：
  描述：

  糠醛 在 丙酮 、 copper dichloride 作用下， 生成 5-(4-chlorophenyl)-2-furancarboxyaldehyde thio semicarbazone
  参考文献：
  名称：

  Malinowski, 1953, vol. 27, p. 54,60

  摘要：

  DOI：

文献信息

• From rational design to serendipity: Discovery of novel thiosemicarbazones as potent trypanocidal compounds
  作者：Saulo Fehelberg Pinto Braga、Viviane Corrêa Santos、Rafael Pinto Vieira、Elany Barbosa da Silva、Ludovica Monti、Susann H. Krake、Pablo D.G. Martinez、Luiz Carlos Dias、Conor R. Caffrey、Jair L. Siqueira-Neto、Renata Barbosa de Oliveira、Rafaela Salgado Ferreira

  DOI：10.1016/j.ejmech.2022.114876

  日期：2022.12

  Here, we describe the design and synthesis of derivatives of our lead compound. The new thiosemicarbazone derivatives showed potency in the nanomolar concentration range against the two enzymes, but they were later characterized as aggregators. Nevertheless, the thiosemicarbazone derivatives showed promising antiparasitic activities against T. b. brucei (EC50 13–49.7 μM) and T. cruzi (EC50 0.027–0.59 μM)

  恰加斯病是由病原体克氏锥虫引起的主要公共卫生问题，估计有 6-7 百万人受到感染，7000 万人面临感染风险。T. brucei gambiense和T. brucei rhodesiense是导致非洲人类锥虫病的相关寄生虫的两个亚种，这是一种被忽视的热带疾病，也有数百万人面临感染风险。这两种疾病的药物治疗都存在疗效低下、副作用或耐药性等问题。最近，我们报道了 cruzain（IC 50 26 μM ，K i 3 μM）和Tbr CatL（IC 5050 μM），两种半胱氨酸蛋白酶被认为是锥虫病有希望的药物靶点。在这里，我们描述了先导化合物衍生物的设计和合成。新的缩氨基硫脲衍生物在纳摩尔浓度范围内显示出对这两种酶的效力，但它们后来被表征为聚集剂。尽管如此，缩氨基硫脲衍生物显示出对T. b.有希望的抗寄生虫活性。brucei (EC 50 13–49.7 μM) 和T. cruzi (EC 50
• Synthesis and Structure−Activity Relationship Study of Potent Trypanocidal Thio Semicarbazone Inhibitors of the Trypanosomal Cysteine Protease Cruzain
  作者：Xiaohui Du、Chun Guo、Elizabeth Hansell、Patricia S. Doyle、Conor R. Caffrey、Tod P. Holler、James H. McKerrow、Fred E. Cohen

  DOI：10.1021/jm010459j

  日期：2002.6.1

  American trypanosomiasis, or Chagas' disease, is the leading cause of heart disease in Latin America. Currently there is an urgent need to develop antitrypanosomal therapy due to the toxicity of existing agents and emerging drug resistance. A novel series of potent thio semicarbazone small-molecule inhibitors of the Trypanosoma cruzi cysteine protease cruzain have been identified. Some of these inhibitors have been shown to be trypanocidal. We initially discovered that X-bromopropiophenone thio semicarbazone (1i) inhibited cruzain and could cure mammalian cell cultures infected with T cruzi. 3'-Bromopropiophenone thio semicarbazone showed no toxicity for mammalian cells at concentrations that were trypanocidal. Following this lead, more than 100 compounds were designed and synthesized. A specific structure-activity relationship (SAR) was established, and many potent analogues with IC50 values in the low nanomolar range were identified. Eight additional analogues were trypanocidal in a cell culture assay, and this indicates that aryl thio semicarbazone is a productive scaffold for killing the parasites. Kinetic studies show that these are time-dependent inhibitors. Molecular modeling studies of the enzyme-inhibitor complex have led to a proposed mechanism of interaction as well as insight into the SAR of the thio semicarbazone series. The nonpeptide nature of this series, small size, and extremely low cost of production suggest this is a promising direction for the development of new antitrypanosome chemotherapy.
• Kalluraya; Vishwanatha; Isloor, Bollettino Chimico Farmaceutico, 2000, vol. 139, # 6, p. 263 - 266
  作者：Kalluraya、Vishwanatha、Isloor、Rai、Kotian

  DOI：——

  日期：——
• Kalluraya, Balakrishna; Vishwanatha; Rahiman, Revue Roumaine de Chimie, 2000, vol. 45, # 1, p. 71 - 75
  作者：Kalluraya, Balakrishna、Vishwanatha、Rahiman

  DOI：——

  日期：——
• Malinowski, 1953, vol. 27, p. 54,60
  作者：Malinowski

  DOI：——

  日期：——