5-nitrofuran-2-carbothioamide | 59-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-nitrofuran-2-carbothioamide
• 英文别名: 5-Nitro-fur-2-ylthiocarbonsaeure-amid；5-Nitrofuran-2-thiocarbonsaeureamid；5-nitro-furan-2-carbothioic acid amide
• CAS: 59-84-7
• 化学式: C₅H₄N₂O₃S
• 分子量: 172.164
• InChiKey: AHYQPLGBKKEXGT-UHFFFAOYSA-N

物化性质

• 沸点：
  319.2±52.0 °C(Predicted)
• 密度：
  1.556±0.06 g/cm3(Predicted)
• 熔点：
  185-187 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitrofuran-2-carbothioamide 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-乙酰氧基甲基-2-(5-硝基-呋喃-2-基)-噻唑
  参考文献：
  名称：

  Antiprotozoal thiazoles. 2. 2-(5-Nitro-2-furyl-, thiazolyl-, and 1-methylimidazolyl-)thiazoles

  摘要：

  Ten 2-substituted 4-thiazolecarboxaldehyde hydrazones bearing 5-nitro-2-furyl, 5-nitro-2-thiazolyl, and 1-methyl-5-nitro-2-imidazolyl functions have been prepared and screened for activity against Trypanosoma cruzi infections in mice. The results permitted the ranking of these substituents in decreasing order of activity: 1-methyl-5-nitro-2-imidazolyl greater than 5-nitro-2-furyl greater than 5-nitro-2-thiazolyl, the last being inactive. Some structural features of the side chain necessary for optimum activity are discussed. The most active compound, 4-[[[2-(1-methyl-5-nitro-2-imidazolyl)-4-thiazolyl]methylene]amino]thiomorpholine 1,1-dioxide, compared favorably with the standard Nifurtimox against three recent clinical isolates of T. cruzi, including one with a high myocardial tissue infiltration.

  DOI：

  10.1021/jm00217a017
• 作为产物：
  描述：

  5-硝基糠腈 、 硫代乙酰胺 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以32%的产率得到5-nitrofuran-2-carbothioamide
  参考文献：
  名称：

  WO2020069625A5

  摘要：

  公开号：

  WO2020069625A5

文献信息

• Syntheses with 5-Nitro-2-furonitrile
  作者：W. R. Sherman、Anne Von Esch

  DOI：10.1021/jm00325a006

  日期：1965.1
• MISHIO SHINSAKU; MATSUMOTO JUN-ICHI; MINAMI SHINSAKU, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR. <YKKZ-AJ>, 1975, 95+
  作者：MISHIO SHINSAKU、 MATSUMOTO JUN-ICHI、 MINAMI SHINSAKU

  DOI：——

  日期：——
• NEVILLE M. C.; VERGE J. P., J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 7, 946-949
  作者：NEVILLE M. C.、 VERGE J. P.

  DOI：——

  日期：——
• WO2020069625A5
  申请人：——

  公开号：WO2020069625A5

  公开（公告）日：2022-10-11
• Antiprotozoal thiazoles. 2. 2-(5-Nitro-2-furyl-, thiazolyl-, and 1-methylimidazolyl-)thiazoles
  作者：Martin C. Neville、John P. Verge

  DOI：10.1021/jm00217a017

  日期：1977.7

  Ten 2-substituted 4-thiazolecarboxaldehyde hydrazones bearing 5-nitro-2-furyl, 5-nitro-2-thiazolyl, and 1-methyl-5-nitro-2-imidazolyl functions have been prepared and screened for activity against Trypanosoma cruzi infections in mice. The results permitted the ranking of these substituents in decreasing order of activity: 1-methyl-5-nitro-2-imidazolyl greater than 5-nitro-2-furyl greater than 5-nitro-2-thiazolyl, the last being inactive. Some structural features of the side chain necessary for optimum activity are discussed. The most active compound, 4-[[[2-(1-methyl-5-nitro-2-imidazolyl)-4-thiazolyl]methylene]amino]thiomorpholine 1,1-dioxide, compared favorably with the standard Nifurtimox against three recent clinical isolates of T. cruzi, including one with a high myocardial tissue infiltration.