2-<(1H-imidazol-1-yl)methyl>pyrrole | 76660-67-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-<(1H-imidazol-1-yl)methyl>pyrrole
• 英文别名: 2-(imidazol-1-ylmethyl) pyrrole；2-(imidazol-1-ylmethyl)-pyrrole；2-[(1H-imidazol-1-yl)methyl]pyrrole；2-(Imidazol-1-ylmethyl)pyrrole；1-(1H-pyrrol-2-ylmethyl)imidazole
• CAS: 76660-67-8
• 化学式: C₈H₉N₃
• mdl: MFCD19220272
• 分子量: 147.18
• InChiKey: NPGFWDXVPSMVHG-UHFFFAOYSA-N

物化性质

• 沸点：
  356.9±17.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-<(1H-imidazol-1-yl)methyl>pyrrole 在 sodium hydride 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 19.33h， 生成 (E)-3-(5-Imidazol-1-ylmethyl-1-methyl-1H-pyrrol-2-yl)-2-methyl-acrylic acid ethyl ester
  参考文献：
  名称：

  [(1H-Imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors

  摘要：

  Several [(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl] pyrroles were prepared and evaluated in vitro as thromboxane synthetase inhibitors in human platelet aggregation studies. A number of structures, e.g. 10b,f,g,i (respective IC50 values: 1 microM, 50 nM, 42 nM, 44 nM) showed superior in vitro inhibition of TXA2 synthetase when compared to the standard dazoxiben (1). However, it was found that in vitro potency did not translate into nor correlate with in vivo activity when these compounds were evaluated in mice in a collagen-epinephrine-induced pulmonary thromboembolism model. (E)-1-Methyl-2-[(1H-imidazol-1-yl)methyl]-5-(2-carboxyprop-1-enyl) pyrrole (10b) was found to offer protection against collagen-epinephrine-induced mortality in mice, thereby demonstrating that oral administration is an effective route for absorption of this drug. Additional evidence for the oral effectiveness of 10b in lowering serum TXB2 levels was obtained by performing ex vivo radioimmunoassay experiments with rats. A 13-week study of 10b in rats with reduced renal mass was conducted in order to evaluate the role of TXA2 production in hypertension and renal dysfunction. Although serum and urinary TXB2 levels in rats were found to be lowered during this study by 10b, the levels of urinary protein excretion remained comparable to that of the control group.

  DOI：

  10.1021/jm00124a027
• 作为产物：
  描述：

  咪唑 、 N,N-二甲基-1-(1H-吡咯-2-基)甲胺 在 乙醚 作用下， 以 邻二甲苯 为溶剂， 反应 3.0h， 以to give 2-(imidazol-1-ylmethyl) pyrrole (15.3 g), m.p. 89°-90°的产率得到2-<(1H-imidazol-1-yl)methyl>pyrrole
  参考文献：
  名称：

  2-(Imidazol-1-ylmethyl)pyrroles

  摘要：

  本发明揭示了2-(咪唑-1-基甲基)吡咯类化合物及其药学上可接受的酸加盐。这些新型化合物可用于选择性地抑制血栓素合成酶酶的作用。

  公开号：

  US04259345A1

文献信息

• 2-(Imidazol-1-ylmethyl)pyrroles
  申请人：Pfizer Inc.

  公开号：US04259345A1

  公开（公告）日：1981-03-31

  Novel 2-(Imidazol-1-ylmethyl)pyrroles and pharmaceutically acceptable acid addition salts thereof are disclosed. The novel compounds are useful in selectively inhibiting the action of the thromboxane synthetase enzyme.

  揭示了新型2-(咪唑-1-基甲基)吡咯烷和其药用可接受的酸盐。这些新化合物在选择性地抑制血栓素合成酶酶的作用方面具有用途。
• Imidazole thromboxane synthetase inhibitors, processes for preparing them, and pharmaceutical compositions containing them
  申请人：Pfizer Limited

  公开号：EP0015155B1

  公开（公告）日：1983-02-23
• US4259345A
  申请人：——

  公开号：US4259345A

  公开（公告）日：1981-03-31
• [(1H-Imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors
  作者：Gregory R. Martinez、Donald R. Hirschfeld、Patrick J. Maloney、Diana S. Yang、Roberto P. Rosenkranz、K. A. M. Walker

  DOI：10.1021/jm00124a027

  日期：1989.4

  Several [(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl] pyrroles were prepared and evaluated in vitro as thromboxane synthetase inhibitors in human platelet aggregation studies. A number of structures, e.g. 10b,f,g,i (respective IC50 values: 1 microM, 50 nM, 42 nM, 44 nM) showed superior in vitro inhibition of TXA2 synthetase when compared to the standard dazoxiben (1). However, it was found that in vitro potency did not translate into nor correlate with in vivo activity when these compounds were evaluated in mice in a collagen-epinephrine-induced pulmonary thromboembolism model. (E)-1-Methyl-2-[(1H-imidazol-1-yl)methyl]-5-(2-carboxyprop-1-enyl) pyrrole (10b) was found to offer protection against collagen-epinephrine-induced mortality in mice, thereby demonstrating that oral administration is an effective route for absorption of this drug. Additional evidence for the oral effectiveness of 10b in lowering serum TXB2 levels was obtained by performing ex vivo radioimmunoassay experiments with rats. A 13-week study of 10b in rats with reduced renal mass was conducted in order to evaluate the role of TXA2 production in hypertension and renal dysfunction. Although serum and urinary TXB2 levels in rats were found to be lowered during this study by 10b, the levels of urinary protein excretion remained comparable to that of the control group.