2-acetylamino-4-methylthiazole-5-carboxylic acid ethyl ester | 2862-33-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-acetylamino-4-methylthiazole-5-carboxylic acid ethyl ester
• 英文别名: ethyl 2-acetylamino-4-methylthiazole-5-carboxylate；ethyl 2-acetamido-4-methylthiazole-5-carboxylate；2-Acetylamino-5-ethoxycarbonyl-4-methylthiazole；2-acetylamino-4-methyl-thiazole-5-carboxylic acid ethyl ester；2-Acetylamino-4-methyl-thiazol-5-carbonsaeure-aethylester；2-Acetamido-4-methyl-5-aethoxycarbonyl-thiazol；Ethyl 2-(acetylamino)-4-methyl-1,3-thiazole-5-carboxylate；ethyl 2-acetamido-4-methyl-1,3-thiazole-5-carboxylate
• CAS: 2862-33-1
• 化学式: C₉H₁₂N₂O₃S
• mdl: MFCD00449854
• 分子量: 228.272
• InChiKey: QCZPLLWOPJAVSX-UHFFFAOYSA-N

物化性质

• 熔点：
  215-217 °C
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetylamino-4-methylthiazole-5-carboxylic acid ethyl ester 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.17h， 生成 potassium dithiocarbazinate
  参考文献：
  名称：

  Baviskar; Shiradkarb; Khadabadia, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 3, p. 321 - 325

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-4-甲基噻唑-5-甲酸乙酯 以 丙酮 为溶剂， 反应 7.0h， 生成 2-acetylamino-4-methylthiazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  与杂环脒的反应，X：一些新的偶氮硫脲衍生物的合成

  摘要：

  通过杂环脒与异硫氰酸乙氧羰基酯或异硫氰酸苯甲酰酯反应制备多种唑基硫脲衍生物。合成的唑基硫脲通过碱和肼处理转化为多环衍生物。

  DOI：

  10.1002/ardp.19823150911

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
• Pseudohalogen chemistry. XI. Some aspects of the chemistry of α-thiocyanato-β-dicarbonyl compounds
  作者：Elaine F. Atkins、Steven Dabbs、Robert G. Guy、Akbar A. Mahomed、Philip Mountford

  DOI：10.1016/s0040-4020(01)85248-0

  日期：1994.1

  Enolised α-thiocyanato-β-dicarbonyl compounds dimerise in ethanol at room temperature to give tautomeric 4,5-disubstituted 2-amino- and 2-acetamido-thiazoles by a C-S-C + C-N cyclisation. Tautomerism is due to the unusual 4-(β-dicarbonyl-α-thio) substituent. Competing intramolecular cyclisations lead to minor amounts of heterocycles containing the thiazole and/or oxathiole ring systems

  烯化的α-硫氰酸根合-β-二羰基化合物在室温下在乙醇中二聚，通过CSC + CN环化反应生成互变异构体4,5-二取代的2-氨基-和2-乙酰氨基-噻唑。互变异构是由于不寻常的4-（β-二羰基-α-硫代）取代基。竞争性的分子内环化反应会导致少量的含有噻唑和/或草硫醇环系统的杂环
• The Reaction of Ketones with Halogens and Thiourea¹
  作者：R. M. Dodson、L. Carroll King

  DOI：10.1021/ja01228a059

  日期：1945.12
• Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles
  作者：N.C. Desai、Nayan Bhatt、Hardik Somani、Amit Trivedi

  DOI：10.1016/j.ejmech.2013.06.029

  日期：2013.9

  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.
• Meakins,G.D.; Willbe,C., Journal of the Chemical Society. Perkin transactions I, 1977, p. 908 - 912
  作者：Meakins,G.D.、Willbe,C.

  DOI：——

  日期：——