(9CI)-吡啶并[1,2-a]苯并咪唑-8-醇 | 123444-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9CI)-吡啶并[1,2-a]苯并咪唑-8-醇
• 英文名称: 8-hydroxypyrido[1,2-a]benzimidazole
• 英文别名: pyridino[1,2-a]benzimidazole-8-ol；8-hydroxo-pyrido{1,2-a}benzimidazole；benz[4,5]imidazo[1,2-a]pyridin-8-ol；Pyrido[1,2-a]benzimidazol-8-ol
• CAS: 123444-29-1
• 化学式: C₁₁H₈N₂O
• mdl: MFCD00819573
• 分子量: 184.197
• InChiKey: ALVJTLMBJPKXLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9CI)-吡啶并[1,2-a]苯并咪唑-8-醇 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 生成 9-Bromo-benzo[4,5]imidazo[1,2-a]pyridin-8-ol
  参考文献：
  名称：

  Structure-activity relationship of bromoeudistomin D, a powerful Ca2+ releaser in skeletal muscle sarcoplasmic reticulum

  摘要：

  Bromoeudistomin D and 9-methyl-7-bromoeudistomin D which have a beta-carboline skeleton are powerful Ca2+ releasers from skeletal muscle sarcoplasmic reticulum exhibiting caffeine-like properties. We examined the effects of bromoeudistomin D analogues on Ca(2+)-induced Ca2+ release from skeletal muscle sarcoplasmic reticulum. Among bromoeudistomin D analogues, the Ca(2+)-releasing activities of carboline derivatives were higher than those of carbazole derivatives, suggesting that a carboline skeleton is significantly important for the manifestation of Ca(2+)-releasing activity and Ca2+ sensitivity of Ca(2+)-induced Ca2+ release. On the contrary, the analogues which have a carbazole skeleton and bromine at C-6 inhibit both Ca(2+)- and caffeine-induced Ca2+ release. 9-Methyl-substitution of the analogue elevated its Ca(2+)-releasing activity. Moreover, there is a close correlation between the enhancement of [3H]ryanodine binding to sarcoplasmic reticulum by the analogues and the activation of Ca2+ release by them. Bromoudistomin D analogues may provide valuable information about the structure-function relationship of the ryanodine receptor/Ca2+ release channels in skeletal muscle sarcoplasmic reticulum.

  DOI：

  10.1016/0922-4106(95)90040-3
• 作为产物：
  描述：

  N-(4-甲氧基苯基)吡啶-2-胺 在 碘苯 、 六氟异丙醇 、 三溴化硼 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (9CI)-吡啶并[1,2-a]苯并咪唑-8-醇
  参考文献：
  名称：

  抑制SSAO/VAP-1的胺类化合物及其在医药上的应用

  摘要：

  本发明涉及一种作为氨基脲敏感性胺氧化酶(SSAO)和/或血管黏附蛋白‑1(VAP‑1)抑制剂的胺类化合物及其在医药上的应用，进一步涉及包含所述化合物的药物组合物。本发明所述的化合物或药物组合物可用于治疗炎症和/或炎症相关疾病、糖尿病和/或糖尿病相关疾病、精神病症、缺血性疾病、血管疾病、纤维化或组织移植排斥。

  公开号：

  CN109988106B

文献信息

• Reaktion von 2-Aminopyridin mit Chinonen
  作者：L. Schmid、H. Czerny

  DOI：10.1007/bf00897797

  日期：1952.1
• Molodkin; Vasilenko; Zaitsev, Russian Journal of Coordination Chemistry, 1997, vol. 23, # 8, p. 543 - 549
  作者：Molodkin、Vasilenko、Zaitsev、Kuznetsov

  DOI：——

  日期：——
• Vasilenko, T. G.; Ermolina, G. E.; Molodkin, A. K., Russian Journal of Inorganic Chemistry, 1989, vol. 34, p. 830 - 833
  作者：Vasilenko, T. G.、Ermolina, G. E.、Molodkin, A. K.、Kuznetsov, S. L.、Prostakov, N. S.、et al.

  DOI：——

  日期：——
• 抑制SSAO/VAP-1的胺类化合物及其在医药上的应用
  申请人：广东东阳光药业有限公司

  公开号：CN109988106B

  公开（公告）日：2023-03-31

  本发明涉及一种作为氨基脲敏感性胺氧化酶(SSAO)和/或血管黏附蛋白‑1(VAP‑1)抑制剂的胺类化合物及其在医药上的应用，进一步涉及包含所述化合物的药物组合物。本发明所述的化合物或药物组合物可用于治疗炎症和/或炎症相关疾病、糖尿病和/或糖尿病相关疾病、精神病症、缺血性疾病、血管疾病、纤维化或组织移植排斥。
• Structure-activity relationship of bromoeudistomin D, a powerful Ca2+ releaser in skeletal muscle sarcoplasmic reticulum
  作者：Yukiko Takahashi、Ken-Ichi Furukawa、Masami Ishibashi、Daisuke Kozutsumi、Haruaki Ishiyama、Jun'ichi Kobayashi、Yasushi Ohizumi

  DOI：10.1016/0922-4106(95)90040-3

  日期：1995.2

  Bromoeudistomin D and 9-methyl-7-bromoeudistomin D which have a beta-carboline skeleton are powerful Ca2+ releasers from skeletal muscle sarcoplasmic reticulum exhibiting caffeine-like properties. We examined the effects of bromoeudistomin D analogues on Ca(2+)-induced Ca2+ release from skeletal muscle sarcoplasmic reticulum. Among bromoeudistomin D analogues, the Ca(2+)-releasing activities of carboline derivatives were higher than those of carbazole derivatives, suggesting that a carboline skeleton is significantly important for the manifestation of Ca(2+)-releasing activity and Ca2+ sensitivity of Ca(2+)-induced Ca2+ release. On the contrary, the analogues which have a carbazole skeleton and bromine at C-6 inhibit both Ca(2+)- and caffeine-induced Ca2+ release. 9-Methyl-substitution of the analogue elevated its Ca(2+)-releasing activity. Moreover, there is a close correlation between the enhancement of [3H]ryanodine binding to sarcoplasmic reticulum by the analogues and the activation of Ca2+ release by them. Bromoudistomin D analogues may provide valuable information about the structure-function relationship of the ryanodine receptor/Ca2+ release channels in skeletal muscle sarcoplasmic reticulum.