4-(4’-methoxy-[1,1’-biphenyl]-4-yl)-2-methylthiazole | 108981-34-6

• 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: 4-(4’-methoxy-[1,1’-biphenyl]-4-yl)-2-methylthiazole
• 英文别名: 4-(4'-methoxybiphenyl-4-yl)-2-methyl-1,3-thiazole；4-(4'-methoxy-biphenyl-4-yl)-2-methyl-thiazole；4-(4'-Methoxy-biphenyl-4-yl)-2-methyl-thiazol；4-[4-(4-Methoxyphenyl)phenyl]-2-methyl-1,3-thiazole；4-[4-(4-methoxyphenyl)phenyl]-2-methyl-1,3-thiazole
• CAS: 108981-34-6
• 化学式: C₁₇H₁₅NOS
• 分子量: 281.378
• InChiKey: GKJUCFVSZMBLCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-甲氧基-联苯-4-基)-乙酮 在 氯仿 、 溴 作用下， 生成 4-(4’-methoxy-[1,1’-biphenyl]-4-yl)-2-methylthiazole
  参考文献：
  名称：

  Sytsch, Ukrainskij Khimicheskij Zhurnal, 1958, vol. 24, p. 79,87

  摘要：

  DOI：

文献信息

• Microwave-Assisted Synthesis of 2-Substituted 4-Biarylyl-1,3-thiazoles by Carbon-Carbon Cross-Coupling in Water
  作者：Kamal Dawood、Moteaa El-Deftar

  DOI：10.1055/s-0029-1218662

  日期：2010.3

  Suzuki-Miyaura and Heck-Mizoroki C-C cross-coupling reactions of 4-(halophenyl)-1,3-thiazoles with aryl(hetaryl)boronic acids or olefins, respectively, were investigated by using a catalytically active benzimidazole-based palladium(II) complex under both thermal and microwave heating conditions in water. The factors affecting the optimization of such reactions were evaluated. palladium - homogeneous

  使用具有催化活性的苯并咪唑基钯（II）研究了4-（卤代苯基）-1,3-噻唑与芳基（杂芳基）硼酸或烯烃的Suzuki-Miyaura和Heck-Mizoroki CC交叉偶联反应在水中的热和微波加热条件下都复杂。评估了影响此类反应最优化的因素。 钯-均相催化-杂环-交叉偶联-微波辅助合成
• Synthesis, in vitro Toxicity, and Antitrypanosomal Activity of Arylated and Diarylated Thiazoles
  作者：Kelly Figueira、Roberson Girão、Krislayne da Costa、Ana Barreto、Maria de Nazaré Soeiro、Jones Limberger

  DOI：10.21577/0103-5053.20230094

  日期：——

  Chagas disease is a relevant public health threat that affects over 6 million people worldwide, resulting in devastating social and economic consequences. Moreover, the therapeutic options are limited, highlighting the urgency in searching for novel active antitrypanosomal molecules. Compounds with either thiazole or biaryl units have been described as possessing anti-Trypanosoma cruzi activities. Therefore, here, we describe the synthesis of nine arylated and diarylated thiazole derivatives and the evaluation of their in vitro toxicity on mammalian cells as well as their anti-T. cruzi activity. The compounds were prepared in straightforward synthetic routes, using Hantzsch thiazole synthesis and cross-coupling reactions as key steps. A pyridylphenyl-thiazole (PPT) derivative (4c) presented 76% of T. cruzi growth inhibition in preliminary tests using a fixed concentration of 20 µM. This compound was used as a scaffold for the synthesis of two novel PPT analogs (4g and 4h). Dose-response assays on intracellular forms of T. cruzi demonstrated that these three compounds presented high antiparasitic potency (half maximal effective concentration (EC50) values ranging from 1.15 to 2.38 μM) and low toxic profile against L929 cell lines. Hence, these findings highlight the pyridyl-phenyl-thiazole backbone as a novel privileged scaffold in the search for active molecules against T. cruzi.

  恰加斯病是一种相关的公共卫生威胁，影响着全球 600 多万人，造成了破坏性的社会和经济后果。此外，治疗方案也很有限，这凸显了寻找新型活性抗盘虫分子的紧迫性。据介绍，含有噻唑或双芳基单元的化合物具有抗克鲁病锥虫的活性。因此，我们在本文中介绍了九种芳基化和二芳基化噻唑衍生物的合成及其对哺乳动物细胞体外毒性和抗克鲁斯绦虫活性的评估。这些化合物的制备采用简单直接的合成路线，关键步骤是汉茨奇噻唑合成和交叉偶联反应。一种吡啶基苯基噻唑（PPT）衍生物（4c）在固定浓度为 20 µM 的初步测试中对 T. cruzi 的生长抑制率为 76%。该化合物被用作合成两种新型 PPT 类似物（4g 和 4h）的支架。对细胞内形式的 T. cruzi 进行的剂量反应试验表明，这三种化合物对 L929 细胞株具有很高的抗寄生效力（半数最大有效浓度 (EC50) 值为 1.15 至 2.38 μM）和低毒性。因此，这些发现凸显了吡啶基-苯基-噻唑骨架在寻找抗击克柔子绦虫的活性分子方面是一种新的特优支架。
• Sytsch, Ukrainskij Khimicheskij Zhurnal, 1958, vol. 24, p. 79,87
  作者：Sytsch

  DOI：——

  日期：——