2-acetamido-4-methylthiazole-5-carboxylic acid hydrazide | 63788-64-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-acetamido-4-methylthiazole-5-carboxylic acid hydrazide
• 英文别名: N-(5-(hydrazinecarbonyl)-4-methylthiazol-2-yl)acetamide；N-[5-(hydrazinecarbonyl)-4-methylthiazol-2-yl]acetamide；2-acetylamino-4-methyl-thiazole-5-carboxylic acid hydrazide；2-Acetamido-4-methyl-thiazol-carbonsaeure-(5)-hydrazid；N-[5-(Hydrazinecarbonyl)-4-methyl-1,3-thiazol-2-yl]acetamide
• CAS: 63788-64-7
• 化学式: C₇H₁₀N₄O₂S
• 分子量: 214.248
• InChiKey: DYCWEMVKEJBCFF-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C(Solv: ethanol (64-17-5))
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetamido-4-methylthiazole-5-carboxylic acid hydrazide 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 N-(4-methyl-5-(5-thioxo-4-((p-tolylamino)methyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl)thiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles

  摘要：

  A series of thiazole clubbed 1,3,4-oxadiazole derivatives (5a-1) have been synthesized and characterized by IR, H-1 NMR, C-13 NMR and mass spectral analysis. Synthesized compounds were evaluated for their antimicrobial and cytotoxic activities. The results indicated that, compounds 5c and 5i exhibited the most potent antibacterial activity. Compound 5f was found to be the most potent antifungal agent. The structure activity relationship revealed that the presence of electron withdrawing groups at para position of phenyl ring remarkably enhanced the antibacterial activity of synthesized compounds. Further, the results of preliminary MIT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 5b, 5c, 5f, 5h and 5i is accompanied by low cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.029
• 作为产物：
  描述：

  2-氨基-4-甲基噻唑-5-甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-acetamido-4-methylthiazole-5-carboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles

  摘要：

  A series of thiazole clubbed 1,3,4-oxadiazole derivatives (5a-1) have been synthesized and characterized by IR, H-1 NMR, C-13 NMR and mass spectral analysis. Synthesized compounds were evaluated for their antimicrobial and cytotoxic activities. The results indicated that, compounds 5c and 5i exhibited the most potent antibacterial activity. Compound 5f was found to be the most potent antifungal agent. The structure activity relationship revealed that the presence of electron withdrawing groups at para position of phenyl ring remarkably enhanced the antibacterial activity of synthesized compounds. Further, the results of preliminary MIT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 5b, 5c, 5f, 5h and 5i is accompanied by low cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.029

文献信息

• Synthesis and Biological Evaluation of Some 2,4,5‐Trisubstituted Thiazole Derivatives as Potential Antimicrobial and Anticancer Agents
  作者：Mohammed S. Al‐Saadi、Hassan M. Faidallah、Sherif A. F. Rostom

  DOI：10.1002/ardp.200800026

  日期：2008.7

  We report on the synthesis and biological evaluation of two series of 2,4,5‐polysubstituted thiazoles comprising the acid hydrazide functionality and some derived pharmacophores known to contribute to various chemotherapeutic activities. All newly synthesized compounds were subjected to in‐vitro antibacterial and antifungal screening. Of the compounds tested, 13 derivatives displayed inhibitory effect

  我们报告了两个系列的 2,4,5-多取代噻唑的合成和生物学评估，这些噻唑包含酸酰肼官能团和一些已知有助于各种化疗活性的衍生药效团。所有新合成的化合物都经过体外抗菌和抗真菌筛选。在测试的化合物中，13 种衍生物对三种革兰氏阳性菌株的生长显示出抑制作用，但对革兰氏阴性菌缺乏活性。此外，四种化合物能够对白色念珠菌发挥抗真菌活性。潜在的抗菌和抗真菌活性与氨基硫脲功能 6a-f 和那些被硫脲基和氨基硫脲部分 12a-f 取代的活性有关。化合物 6f 和 12f（R = 4-F-C6H4）可以被认为是本研究中最活跃的成员，对三种类型的革兰氏阳性菌具有广谱的抗菌活性，同时对白色念珠菌具有明显的抗真菌活性. 化合物 6d、6f 和 12f 对枯草芽孢杆菌的活性是氨苄青霉素的两倍。最好的抗真菌活性表现为化合物 6d 的活性比克霉唑低 50%。根据 NCI 当前的单剂量方案，选择并测试了 17 种化合物的初步体外抗癌活性。三种细胞系，非小细胞肺癌
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