5-Nitrothiazol-2-thiocarbonsaeureamid | 36557-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Nitrothiazol-2-thiocarbonsaeureamid
• 英文别名: 5-nitro-thiazole-2-carbothioic acid amide；5-Nitro-1,3-thiazole-2-carbothioamide
• CAS: 36557-37-6
• 化学式: C₄H₃N₃O₂S₂
• 分子量: 189.219
• InChiKey: VESSLLZYBASIFT-UHFFFAOYSA-N

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：
  145
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Nitrothiazol-2-thiocarbonsaeureamid 以76%的产率得到
  参考文献：
  名称：

  NEVILLE M. C.; VERGE J. P., J. MED. CHEM. , 1977, 20, NO 7, 946-949

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基-1,3-噻唑-2-甲腈 在 盐酸 、 硫代乙酰胺 、 N,N-二甲基甲酰胺 作用下， 生成 5-Nitrothiazol-2-thiocarbonsaeureamid
  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

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。