4,5-bis(4-methoxyphenyl)-2-(4-pyridyl)thiazole | 130735-43-2

• 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-methoxyphenyl)-2-(4-pyridyl)thiazole
• 英文别名: 4,5-bis(4-methoxyphenyl)-2-pyridin-4-yl-1,3-thiazole
• CAS: 130735-43-2
• 化学式: C₂₂H₁₈N₂O₂S
• 分子量: 374.463
• InChiKey: MCOJYVGZYMGSAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-bis(4-methoxyphenyl)-2-(4-pyridyl)thiazole 、 碘甲烷 在 4,5-Bis(4-methoxyphenyl)-2-(1-methylpyridin-1-ium-4-yl)-1,3-thiazole;iodide 、 甲醇 、 硼氢化钠 、 水 、 氯仿 、 Brine 、 magnesium sulfate 作用下， 以 氯仿 、 甲醇 为溶剂， 反应 49.0h， 以to give 4,5-bis(4-methoxyphenyl)-2-(1-methyl-1,2,5,6-tetrahydro-4-pyridyl)thiazole (0.16 g)的产率得到4,5-bis(4-methoxyphenyl)-2-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)thiazole
  参考文献：
  名称：

  Thiazole compounds and pharmaceutical composition comprising the same

  摘要：

  本发明揭示了式##STR1##中所定义的取代基的噻唑化合物具有抗血栓、扩张血管、抗过敏、抗炎和5-脂氧合酶抑制活性。

  公开号：

  US05217971A1
• 作为产物：
  描述：

  茴香偶姻 在 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4,5-bis(4-methoxyphenyl)-2-(4-pyridyl)thiazole
  参考文献：
  名称：

  Antiplatelet Agents Based on Cyclooxygenase Inhibition without Ulcerogenesis. Evaluation and Synthesis of 4,5-Bis(4-methoxyphenyl)-2-substituted-thiazoles

  摘要：

  The syntheses, biological evaluations, and structure-activity relationships of a series of 4,5-bis-( 4-methoxyphenyl)-2-substituted-thiazoles as potent antiplatelet agents with vasodilatory activity are described. 2-Guanidino-4,5-bis(4-methoxyphenyl) thiazole (3), designed from two parent compounds (itazigrel and timegadine), showed inhibitory activity of malondialdehyde (MDA, IC50 = 31 mu M) production which is formed from the cyclooxygenase (CO)-catalyzed oxygenation of arachidonic acid in the synthesis of prostanoids in platelets, with vasodilatory activity (ED(50) 2.0 mu M). Further structure-activity relationship studies on 3 culminated in the preparation of 4,5-bis(4-methoxyphenyl)-2-[(1-methylpiperazin-4-yl)carbonyl] thiazole (10a, FR122047) which exhibited potent inhibitory activity on MDA synthesis in vitro (IC50 = 0.088 mu M) and platelet aggregation in guinea pigs ex vivo (100% inhibition even 6 h after 1.0 mg/kg administration) with vasodilatory activity in vitro (ED(50) = 6.2 mu M). Moreover, 10a demonstrated no ulcerogenesis effect in rats even at 100 mg/kg dosage (safety margin in rats is more than 70 while that of aspirin is only 1.2) in spite of its potent CO inhibition (IC50 = 0.43 mu M(14)), while the use of aspirin, a CO inhibitor and the most popular thromboembolic drug, is restricted by the side effect.(8) Pharmacokinetic studies on 10a have revealed that 10a is detectable in platelet-rich plasma but not in platelet-poor plasma 1 day after oral administration, which indicates that 10a tends to be localized in platelets. This property could be responsible for its low toxicity and reduction of side effects in clinical studies.

  DOI：

  10.1021/jm00034a017

文献信息

• Thiazole compounds and pharmaceutical composition comprising the same
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05217971A1

  公开（公告）日：1993-06-08

  Thiazole compounds of the formula ##STR1## wherein the substituents are defined herein are disclosed as having antithrombotic, vasodilating, antiallergic, antiinflammatory and 5-lipoxygenase inhibitory activity.

  本发明揭示了式##STR1##中所定义的取代基的噻唑化合物具有抗血栓、扩张血管、抗过敏、抗炎和5-脂氧合酶抑制活性。
• Thiazole compounds, processes for the preparation thereof, and pharmaceutical composition comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0377457A1

  公开（公告）日：1990-07-11

  The present invention relates to new thiazole compounds and pharmaceutically acceptable salts thereof which have pharmacological activities, processes for preparation thereof, a pharmaceutical composition comprising the same same and a use of the same.

  本发明涉及具有药理活性的新噻唑化合物及其药学上可接受的盐、其制备工艺、包含相同物质的药物组合物以及相同物质的用途。
• Substituted thiazoles for the treatment of inflammation
  申请人：G.D. SEARLE & CO.

  公开号：EP1125932A2

  公开（公告）日：2001-08-22

  A class of substituted thiazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II wherein R4 is selected from methyl and amino; wherein R5 is selected from optionally substituted aryl, cycloalkyl, cycloalkenyl and heterocyclic; and wherein R6 is selected from hydrogen or specified substituents; or a pharmaceutically-acceptable salt thereof.

  描述了一类用于治疗炎症和炎症相关疾病的取代噻唑化合物。特别感兴趣的化合物由式 II 定义 其中 R4 选自甲基和氨基；其中 R5 选自任选取代的芳基、环烷基、环烯基和杂环基；其中 R6 选自氢或特定取代基；或其药学上可接受的盐。
• US5217971A
  申请人：——

  公开号：US5217971A

  公开（公告）日：1993-06-08
• US5668161A
  申请人：——

  公开号：US5668161A

  公开（公告）日：1997-09-16