4,5-Bis-(4-methoxy-phenyl)-2-thiophen-3-yl-1H-imidazole | 134789-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-Bis-(4-methoxy-phenyl)-2-thiophen-3-yl-1H-imidazole
• 英文别名: 4,5-bis(4-methoxyphenyl)-2-thiophen-3-yl-1H-imidazole
• CAS: 134789-85-8
• 化学式: C₂₁H₁₈N₂O₂S
• 分子量: 362.452
• InChiKey: RFHNRZVYSZWTTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  75.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-噻吩甲醛 、 4,4'-二甲氧基苯酚酯 在 ammonium acetate 、 溶剂黄146 作用下， 以64%的产率得到4,5-Bis-(4-methoxy-phenyl)-2-thiophen-3-yl-1H-imidazole
  参考文献：
  名称：

  Synthesis and platelet aggregation inhibitory activity of diphenylazole derivatives. I. Thiazole and imidazole derivatives.

  摘要：

  合成了二苯基咪唑和二苯基噻唑衍生物，并在兔子的体外实验中将其作为血小板聚集抑制剂进行了测试。在抑制花生四烯酸诱导的兔子富血小板血浆血小板聚集方面，二苯基噻唑衍生物（10）比二苯基咪唑衍生物（4）更有效。用豚鼠评估了两种二苯基咪唑和八种二苯基噻唑衍生物对花生四烯酸和胶原蛋白诱导的血小板聚集的体内外抑制活性。在这些化合物中，4, 5-双（4-甲氧基苯基）-2-（1, 5-二甲基-2-吡咯基）噻唑（10n）在体外和体内均表现出很强的活性。10n 的体内外活性比阿司匹林强 200 倍。10n 的活性机制是抑制环氧化酶。

  DOI：

  10.1248/cpb.39.651

文献信息

• Synthesis and platelet aggregation inhibitory activity of diphenylazole derivatives. I. Thiazole and imidazole derivatives.
  作者：Norihiko SEKO、Kohichiro YOSHINO、Koichi YOKOTA、Goro TSUKAMOTO

  DOI：10.1248/cpb.39.651

  日期：——

  Diphenylimidazole and diphenylthiazole derivatives were synthesized and tested as inhibitors of platelet aggregation in in vitro experiments with the rabbit. Diphenylthiazole derivatives (10) were more potent than diphenylimidazole derivatives (4) in inhibiting arachidonic acid-induced platelet aggregation of rabbit platelet-rich plasma. Two diphenylimidazole and eight diphenylthiazole derivatives were evaluated for ex vivo arachidonic acid and collagen-induced platelet aggregation inhibitory activity using guinea pigs. In these compounds, 4, 5-bis(4-methoxyphenyl)-2-(1, 5-dimethyl-2-pyrrolyl)thiazole (10n) showed strong activity in vitro and ex vivo. The ex vivo activity of 10n was 200 times stronger than that of aspirin. The mechanism of the activity of 10n was the inhibition of cyclo-oxygenase.

  合成了二苯基咪唑和二苯基噻唑衍生物，并在兔子的体外实验中将其作为血小板聚集抑制剂进行了测试。在抑制花生四烯酸诱导的兔子富血小板血浆血小板聚集方面，二苯基噻唑衍生物（10）比二苯基咪唑衍生物（4）更有效。用豚鼠评估了两种二苯基咪唑和八种二苯基噻唑衍生物对花生四烯酸和胶原蛋白诱导的血小板聚集的体内外抑制活性。在这些化合物中，4, 5-双（4-甲氧基苯基）-2-（1, 5-二甲基-2-吡咯基）噻唑（10n）在体外和体内均表现出很强的活性。10n 的体内外活性比阿司匹林强 200 倍。10n 的活性机制是抑制环氧化酶。
• Metal chloride hydrates as Lewis acid catalysts in multicomponent synthesis of 2,4,5-triarylimidazoles or 2,4,5-triaryloxazoles
  作者：Marcelo V. Marques、Marcelo M. Ruthner、Luiz A. M. Fontoura、Dennis Russowsky

  DOI：10.1590/s0103-50532012000100024

  日期：——

  A series of nine metal chloride hydrates (ZnCl2 center dot 2H(2)O, SnCl2 center dot 2H(2)O, CdCl2 center dot 2H(2)O, MnCl2 center dot 4H(2)O, CoCl2 center dot 6H(2)O, SrCl2 center dot 6H(2)O, NiCl2 center dot 6H(2)O, CrCl3 center dot 6H(2)O and CeCl3 center dot 7H(2)O) was investigated as mild and inexpensive Lewis acid catalysts to promote the multicomponent synthesis of triarylimidazoles. Reactions starting from benzil showed the best results when SnCl2 center dot 2H(2)O was used, while for benzoin as the starting material, CeCl3 center dot 7H(2)O was more efficient. All reactions were performed in EtOH as solvent. These catalysts were also successfully employed in the synthesis of triaryloxazoles.