2-(1H-咪唑-1-基)-6-甲氧基-1,2,3,4-四氢萘-1-醇 | 886040-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2-(1H-咪唑-1-基)-6-甲氧基-1,2,3,4-四氢萘-1-醇
• 英文名称: 2-(1H-imidazol-1-yl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
• 英文别名: 2-Imidazol-1-yl-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS: 886040-24-0
• 化学式: C₁₄H₁₆N₂O₂
• mdl: MFCD16235884
• 分子量: 244.293
• InChiKey: VPMJJOUHFSYBHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-咪唑-1-基)-6-甲氧基-1,2,3,4-四氢萘-1-醇 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以78%的产率得到1-(6-甲氧基-3,4-二氢萘-2-基)咪唑
  参考文献：
  名称：

  N-imidazolyl derivatives of the napththalene and chroman rings as thromboxane A2 synthase inhibitors

  摘要：

  A series of N-imidazol-1-yl derivatives of 1,2-dihydronaphthalene, 1,2,3,4-tetrahydronaphthalene, 2H-1-benzopyran and some related compounds were synthesized and tested as inhibitors of thromboxane A2 synthase in ex vivo experiments with orally treated rats. Some compounds showed good activity which was confirmed in experiments in vitro in rabbit whole blood. Some structural requirements for significant TxA2 synthase inhibitory activity are discussed. The selected 5,6-Dihydro-7-(H-1-imidazol-1-yl)-2-naphthalene-carboxylic acid (compound 7) was conformationally analysed using the Sybyl molecular model system in comparison with dazoxiben. Compound 7 was further pharmacologically investigated and on the basis of its interesting activities in vitro, ex vivo and in vivo and its low toxicity was selected for clinical investigation.

  DOI：

  10.1016/0223-5234(91)90103-t
• 作为产物：
  描述：

  6-甲氧基-1-萘满酮 在 sodium tetrahydroborate 、 tetra-N-butylammonium tribromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-(1H-咪唑-1-基)-6-甲氧基-1,2,3,4-四氢萘-1-醇
  参考文献：
  名称：

  Synthesis and Evaluation of Heteroaryl-Substituted Dihydronaphthalenes and Indenes:  Potent and Selective Inhibitors of Aldosterone Synthase (CYP11B2) for the Treatment of Congestive Heart Failure and Myocardial Fibrosis

  摘要：

  In this study, the synthesis and biological evaluation of heteroaryl-substituted dihydronaphthalenes and indenes (1-16) is described. The compounds were tested for activity by use of human CYP11B2 expressed in fission yeast and V79 MZh cells and for selectivity by use of human CYP11B1, CYP17, and CYP19. The most active inhibitor was the 6-methoxydihydronaphthalene 4 (IC50 = 2 nM), showing a K-i value of 1.3 nM and a competitive type of inhibition. The 5-methoxyindene 3 was found to be the most selective CYP11B2 inhibitor (IC50 = 4 nM; CYP11B1 IC50 = 5684 nM), which also showed only marginal inhibition of human CYP3A4 and CYP2D6. Docking and molecular dynamics studies using our homology-modeled CYP11B2 structure were performed to understand some structure-activity relationships. Caco-2 cell experiments revealed highly cell-permeable compounds, and metabolic studies with 4 using rat liver microsomes showed sufficient stability.

  DOI：

  10.1021/jm060055x