N-[4-(2-methyl-4-thiazolyl)phenyl]acetamide | 65321-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-(2-methyl-4-thiazolyl)phenyl]acetamide
• 英文别名: 4-(2-methyl-4-thiazolyl)acetanilide；N-[4-(2-methyl-thiazol-4-yl)-phenyl]-acetamide；2-Methyl-4-p-acetylaminophenylthiazol；N-[4-(2-methyl-1,3-thiazol-4-yl)phenyl]acetamide
• CAS: 65321-91-7
• 化学式: C₁₂H₁₂N₂OS
• mdl: MFCD00728748
• 分子量: 232.306
• InChiKey: BTEXZWFJUVMEQM-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  455.4±28.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[4-(2-methyl-4-thiazolyl)phenyl]acetamide 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以92%的产率得到4-(2-甲基-1,3-噻唑-4-基)苯胺
  参考文献：
  名称：

  含有（苯）唑部分的N- [4-（2-甲基噻唑-4-基）苯基]乙酰胺衍生物的合成及抗癌活性评估。

  摘要：

  合成了一类新型的新型噻唑-（苯并）唑衍生物以研究其抗癌活性。化合物的结构通过IR，（1）H-NMR和MS光谱数据以及元素分析确认。评价了化合物对A549和C6肿瘤细胞系的抗癌作用。进行了MTT，DNA合成分析，a啶橙/溴化乙锭染色方法和caspase-3活化分析，以进行抗癌活性研究。带有5-氯和5-甲基苯并咪唑基的化合物6f和6g显示出显着的抗癌活性。还观察到这些化合物将肿瘤细胞引导至凋亡途径的潜力，这是抗癌作用的前提。

  DOI：

  10.3109/14756366.2013.763253
• 作为产物：
  描述：

  4-乙酰胺苯乙酮 在 氢溴酸 、 溴 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 49.0h， 生成 N-[4-(2-methyl-4-thiazolyl)phenyl]acetamide
  参考文献：
  名称：

  Synthesis, anticandidal activity, and cytotoxicity of some thiazole derivatives with dithiocarbamate side chains

  摘要：

  为了研究一些噻唑衍生物的抗真菌活性和细胞毒性，合成了一系列含有二硫代氨基甲酸酯的噻唑类化合物。通过光谱数据（IR、¹H NMR、¹³C NMR 和 MS）和元素分析确认了所得最终化合物（6a-j）的结构。采用微量肉汤稀释法测定这些化合物的抗真菌活性（6a-j），并通过MTT（3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑盐溴）法测定其对正常细胞的细胞毒性。与预期相反，观察到的抗真菌活性较弱，IC₅₀值在30至403 µg/mL之间。

  DOI：

  10.3906/kim-1312-62

文献信息

• Design, synthesis and evaluation of new thiazole-piperazines as acetylcholinesterase inhibitors
  作者：Leyla Yurttaş、Zafer Asım Kaplancıklı、Yusuf Özkay

  DOI：10.3109/14756366.2012.709242

  日期：2013.10.1

  In this study, some new 2-(4-substituted piperazine-1-yl)-N-[4-(2-methylthiazol-4-yl)phenyl]acetamide derivatives were synthesized. The synthesized compounds were screened for their anticholinesterase activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes by in vitro Ellman's method. The structural elucidation of the compounds was performed by using IR, H-1-NMR, C-13-NMR and FAB(+)-MS spectral data and elemental analyses results. Biological assays revealed that at 0.1 mu M concentration, the most active compounds against AChE were 5n, 5o and 5p that indicated 96.44, 99.83 and 89.70% inhibition rates, respectively. Besides, IC50 value of the compound 5o was determined as 0.011 mu M, whereas IC50 value of standard drug donepezil was 0.054 mu M. The synthesized compounds did not show any notable inhibitory activity against BChE.
• Synthesis and Anticancer Activities of Some Thiazole Derivatives
  作者：Ismail Kayagil、Seref Demirayak

  DOI：10.1080/10426500802446181

  日期：2009.9.18

  In this study, 2-substituted 4-[3/4-(4-arylthiazole-2-yl) aminophenyl] thiazole derivatives and 2-[4-[2-substituted 4-methylthiazole-5-yl]thiazole-2-yl] amino-5-arylidenethiazoline-4-one derivatives have been synthesized. The cytotoxic and/or growth inhibitory effects of the 16 selected compounds were evaluated in vitro against approximately 66 human tumor cell lines derived from nine neoplastic diseases. Some of the compounds were found to act as anticancer agents.
• Yurchenko,R.I.; Malitskaya,V.P., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 1839 - 1845
  作者：Yurchenko,R.I.、Malitskaya,V.P.

  DOI：——

  日期：——
• YURCHENKO R. I.; MALITSKAYA V. P., ZH. ORGAN. XIMII, 1977, 13, HO 9, 1980-
  作者：YURCHENKO R. I.、 MALITSKAYA V. P.

  DOI：——

  日期：——
• SMALL-MOLECULE UT-A-SELECTIVE UREA TRANSPORT INIHIBITORS
  申请人：The Regents of the University of California

  公开号：US20170239235A1

  公开（公告）日：2017-08-24

  Provided herein are compounds that are urea transporter-A inhibitors that are useful for producing a strong diuretic response and may be used for treating refractory edema associated with cardiovascular, renal, and metabolic diseases, disorders, and conditions.