1-methyl-5-nitro-1H-imidazole-2-carbothioic acid amide | 57436-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-5-nitro-1H-imidazole-2-carbothioic acid amide
• 英文别名: 1-methyl-2-thiocarbamyl-5-nitroimidazole；1-Methyl-5-nitroimidazol-2-thiocarbonsaeureamid；1-methyl-5-nitroimidazole-2-carbothioamide
• CAS: 57436-49-4
• 化学式: C₅H₆N₄O₂S
• 分子量: 186.194
• InChiKey: LJWUMPBTNPLHAG-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  418.6±37.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-5-nitro-1H-imidazole-2-carbothioic acid amide 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-thiazole-4-carbaldehyde
  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：

  硫代乙酰胺 、 1-甲基-5-硝基咪唑-2-甲腈 以 N-甲基乙酰胺 为溶剂， 生成 1-methyl-5-nitro-1H-imidazole-2-carbothioic acid amide
  参考文献：
  名称：

  Thiazole derivatives

  摘要：

  2-硝基咪唑基-4-硫代吗啉亚胺烷基噻唑醇类化合物可作为抗寄生虫药物，对锥虫科活性良好，并可通过新型2-硝基咪唑基-4-酰基噻唑醇与N-氨基吗啉亚胺反应制备。

  公开号：

  US03989690A1

文献信息

• Synthesis and in vitro antibacterial activities of 3-thiazol 4 yl-carba-l-dethiacephalosporins.
  作者：WILLIAM J. HORNBACK、JOHN E. MUNROE、FRED T. COUNTER

  DOI：10.7164/antibiotics.47.1052

  日期：——

  The synthesis and microbiological evaluation of a new series of 3-thiazol-4-yl-carba-1-dethiacephalosporins is described. Structure activity relationship was achieved by changing substitution at the 2-position of the thiazole moiety. The result was a marked variance of microbiological activity in the C7 side-chain derivatives. ATMO derivatives possess potent activity against both Gram-positive and Gram-negative bacteria. For example, MICs (μg/ml) of LY215226 against representative organisms are as follows: S. aureus 0.25, S. pneumoniae 0.008, H. influenzae 0.008, E. coli 0.25, K. pneumoniae 0.008, E. cloacae 0.5, S. typhi 0.25, and M. morganii 0.25.

  描述了一系列新的3-噻唑-4-基-卡巴-1-去硫头孢菌素的合成和微生物学评估。通过改变噻唑部分的2位取代来实现结构-活性关系。结果表明，C7侧链衍生物在微生物活性上存在明显差异。ATMO衍生物对革兰阳性和革兰阴性细菌均具有强效活性。例如，LY215226对典型微生物的最低抑菌浓度（MIC，μg/ml）如下：金黄色葡萄球菌0.25，肺炎链球菌0.008，流感嗜血杆菌0.008，大肠杆菌0.25，肺炎克雷伯菌0.008，克隆氏菌0.5，伤寒沙门氏菌0.25，以及摩根氏菌0.25。
• Winkelmann; Raether; Gebert, Arzneimittel-Forschung/Drug Research, 1977, vol. 27, # 12, p. 2251 - 2263
  作者：Winkelmann、Raether、Gebert、Sinharay

  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：——