5-(1-phenyl-1H-indazol-3-yl)-furan-2-carboxylic acid methyl ester | 58972-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(1-phenyl-1H-indazol-3-yl)-furan-2-carboxylic acid methyl ester
• 英文别名: 3-(5-Methoxycarbonyl-2-furyl)-1-phenylindazole；Methyl 5-(1-phenylindazol-3-yl)furan-2-carboxylate
• CAS: 58972-30-8
• 化学式: C₁₉H₁₄N₂O₃
• 分子量: 318.332
• InChiKey: INEPBFYAULNXSI-UHFFFAOYSA-N

物化性质

• 沸点：
  456.5±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(1-phenyl-1H-indazol-3-yl)-furan-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 生成 5-(1-phenyl-1H-indazol-3-yl)-furan-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole Analogues as Novel Antiplatelet Agents

  摘要：

  1-Benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (28, YC-1) was selected as the lead compound for systemic structural modification. After screening for antiplatelet activity, SARs of YC-1 analogues were established. Among these potent active derivatives, compounds 29, 30, 31, 44, and 45 functioned as potent activators of sGC and inhibitors of PDE5 with potency comparable to that of YC-1. In addition, compound 58 was found to be a selective and potent inhibitor of protease-activated receptor type 4 (PAR4)-dependent platelet activation.

  DOI：

  10.1021/jm010001h
• 作为产物：
  描述：

  5-苯甲酰基呋喃-2-甲酸甲酯 在 三氟化硼乙醚 、 溶剂黄146 作用下， 生成 5-(1-phenyl-1H-indazol-3-yl)-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole Analogues as Novel Antiplatelet Agents

  摘要：

  1-Benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (28, YC-1) was selected as the lead compound for systemic structural modification. After screening for antiplatelet activity, SARs of YC-1 analogues were established. Among these potent active derivatives, compounds 29, 30, 31, 44, and 45 functioned as potent activators of sGC and inhibitors of PDE5 with potency comparable to that of YC-1. In addition, compound 58 was found to be a selective and potent inhibitor of protease-activated receptor type 4 (PAR4)-dependent platelet activation.

  DOI：

  10.1021/jm010001h

文献信息

• YOSHINA SHIGETAKA; TANAKA AKIRA; KUO SHENG-CHU, YAKUGAKU DZASSI, YAKU
  作者：YOSHINA SHIGETAKA、 TANAKA AKIRA、 KUO SHENG-CHU

  DOI：——

  日期：——
• JPH07224057A
  申请人：——

  公开号：JPH07224057A

  公开（公告）日：1995-08-22
• 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole (YC-1) Derivatives as Novel Inhibitors Against Sodium Nitroprusside-Induced Apoptosis
  作者：Jin-Cherng Lien、Fang-Yu Lee、Li-Jiau Huang、Shiow-Lin Pan、Jih-Hwa Guh、Che-Ming Teng、Sheng-Chu Kuo

  DOI：10.1021/jm020070b

  日期：2002.11.1

  Antiapoptotic agents based on 1-benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (22, YC-1) derivatives were explored for effective treatment of sepsis and septic shock. We found that compound 22, 1-benzyl-3-(5'-methoxymethyl-2'-furyl)indazole (27), and 1-phenyl-3-(5'-hydroxymethyl-2'-furyl)-indazole (23) were the most effective inhibitors of sodium nitroprusside-induced vascular smooth muscle cell apoptosis. These three compounds are proposed as potential therapeutic agents for the treatment of sepsis.
• Synthesis of 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole Analogues as Novel Antiplatelet Agents
  作者：Fang-Yu Lee、Jin-Cherng Lien、Li-Jiau Huang、Tsang-Miao Huang、Sheng-Chung Tsai、Che-Ming Teng、Chin-Chung Wu、Fong-Chi Cheng、Sheng-Chu Kuo

  DOI：10.1021/jm010001h

  日期：2001.10.1

  1-Benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (28, YC-1) was selected as the lead compound for systemic structural modification. After screening for antiplatelet activity, SARs of YC-1 analogues were established. Among these potent active derivatives, compounds 29, 30, 31, 44, and 45 functioned as potent activators of sGC and inhibitors of PDE5 with potency comparable to that of YC-1. In addition, compound 58 was found to be a selective and potent inhibitor of protease-activated receptor type 4 (PAR4)-dependent platelet activation.