S-<2-(trifluoromethyl)quinazolin-4-yl>thioglycolic acid | 95616-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: S-<2-(trifluoromethyl)quinazolin-4-yl>thioglycolic acid
• 英文别名: 2-trifluoromethyl-(quinazolin-4-ylthio)acetic acid；2-[2-(Trifluoromethyl)quinazolin-4-yl]sulfanylacetic acid
• CAS: 95616-40-3
• 化学式: C₁₁H₇F₃N₂O₂S
• 分子量: 288.25
• InChiKey: USHBBUVBDHPUJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氨基硫代苯甲酰胺 在 molecular sieve 、 三乙胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 5.0h， 生成 S-<2-(trifluoromethyl)quinazolin-4-yl>thioglycolic acid
  参考文献：
  名称：

  Annulation to the quinazoline ring utilizing mesoionic ring systems

  摘要：

  DOI：

  10.1021/jo00210a021

文献信息

• Synthesis, Anticancer, and QSAR Studies of 2-Alkyl(aryl,hetaryl)quinazolin-4(3<i>H</i>)-thione's and [1,2,4]Triazolo[1,5-<i>c</i>]quinazoline-2-thione's Thioderivatives
  作者：Oleksii M. Antypenko、Sergiy I. Kovalenko、Oleksandr V. Karpenko、Vladyslav O. Nikitin、Lyudmyla M. Antypenko

  DOI：10.1002/hlca.201600062

  日期：2016.8

  Considering the frightening high level of mortality from cancer, studies of anticancer agents are vital nowadays. The 24 thioderivatives of 2‐alkyl(aryl)‐quinazolin‐4(3H)‐thiones and 20 thioderivatives of [1,2,4]triazolo[1,5‐c]quinazoline‐2‐thiones were synthesized and evaluated for preliminary in vitro anticancer activity with subsequent in silico QSAR analysis. The substance 18 had the best results

  考虑到可怕的高死亡率，目前抗癌药物的研究至关重要。合成了24个2-烷基（芳基）-喹唑啉-4（3 H）-硫酮的硫代衍生物和20种[1,2,4]三唑并[1,5 - c ]喹唑啉-2-硫酮的硫代衍生物并进行了初步评估体外抗癌活性以及随后的计算机QSAR分析。物质18具有抑制八种癌细胞生长的最佳结果：白血病的CCRF-CEM；中枢神经系统癌的SF-539，SNB-75和U251；786，RXF393和UO-31肾癌；乳腺癌的MDA‐MB‐231 / ATCC（−31.50 – 47.41％的细胞生长）效果低。计算得出的白血病CCRF-CEM，乳腺癌T-47D和HS 578T的QSAR模型以及平均细胞生长显示出良好的抗癌活性预测率（r 2  = 0.7 – 0.8， = 0.5 – 0.7）。
• 2-Alkyl(aryl)-quinazolin-4(3<i>H</i>)-thiones, 2-R-(quinazolin-4(3<i>H</i>)-ylthio)carboxylic acids and amides: synthesis, molecular docking, antimicrobial and anticancer properties
  作者：Lyudmyla Antypenko、Sergiy Kovalenko、Yulia Posylkina、Vladyslav Nikitin、Natalia Fedyunina、Vitalii Ivchuk

  DOI：10.3109/14756366.2015.1018243

  日期：2016.3.3

  In this study, a series of novel 2-alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides were synthesized and evaluated for antimicrobial and anticancer activities. Their structure was confirmed by elemental analysis and spectral data (FT-IR, LC-MS, H-1-NMR). Antimicrobial activity was tested in vitro against Staphylococcus aureus, Enterococcus faecalis, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, Candida albicans and NCI in vitro preliminary anticancer activity against nine different cancer types. The most active antibacterial and antifungal compounds were: 2.1, 2.2 and 2.4. The introduction of the carboxylic acid or amide residue into the fourth position of quinazolin-4(3H)-thione resulted in the absence of antimicrobial activity. Substance 3.8 inhibited renal cancer UO-31 line and 2.18 - leukemia CCRF-CEM. The results of in silico molecular docking for DHFR and CK2 kinase had no correlation with in vitro properties, proposing the presence of other biological activity pathways.
• POTTS, K. T.;BORDEAUX, K. G.;KUEHNLING, W. R.;SALSBURY, R. L., J. ORG. CHEM., 1985, 50, N 10, 1666-1676
  作者：POTTS, K. T.、BORDEAUX, K. G.、KUEHNLING, W. R.、SALSBURY, R. L.

  DOI：——

  日期：——
• Annulation to the quinazoline ring utilizing mesoionic ring systems
  作者：Kevin T. Potts、Kirk G. Bordeaux、William R. Kuehnling、Ronald L. Salsbury

  DOI：10.1021/jo00210a021

  日期：1985.5