1-(4-Fluoro-phenyl)-7-naphthalen-1-ylmethyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde | 144147-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-Fluoro-phenyl)-7-naphthalen-1-ylmethyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde
• 英文别名: 1-(4-fluorophenyl)-7-(naphthalen-1-ylmethyl)-4,5,6,7-tetrahydroindazole-3-carbaldehyde
• CAS: 144147-90-0
• 化学式: C₂₅H₂₁FN₂O
• 分子量: 384.453
• InChiKey: AODALVDMGJGCNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-Fluoro-phenyl)-7-naphthalen-1-ylmethyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成 1-(4-Fluoro-phenyl)-7-naphthalen-1-ylmethyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde oxime
  参考文献：
  名称：

  Synthesis and progesterone receptor binding affinity of substituted 1-phenyl-7-benzyl-4,5,6,7-tetrahydro-1-indazoles

  摘要：

  Research directed toward the discovery of non-steroidal ligands for steroid receptors led to the preparation of a series of substituted 1-phenyl-7-benzyltetrahydroindazole-3-carboxaldehydes. Appropriately substituted 3-formyl analogs (4) were found to bind with high affinity to progesterone receptors and showed agonist activity in human T47D cells but were inactive in several in vivo models for progestational activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10016-6
• 作为产物：
  描述：

  2-(1-naphthylmethyl)cyclohexanone 在 盐酸 、 正丁基锂 、 sodium acetate 、 二异丙胺 作用下， 反应 4.75h， 生成 1-(4-Fluoro-phenyl)-7-naphthalen-1-ylmethyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde
  参考文献：
  名称：

  HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts

  摘要：

  Compounds comprising a series of 7-[2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-3,5-dihydroxy-6-heptenoic acid sodium salts (18) were synthesized and tested for their ability to inhibit HMG-CoA reductase in a partially purified enzyme preparation and cholesterol biosynthesis from acetate in cultured HEP-G2 cells. Changing the size of the saturated ring of the tetrahydroindazole nucleus did not improve potency, but incorporation of substituents at the 7-position resulted in up to 1700-fold improvement in inhibitory potency. Structure-activity studies revealed that the most potent compounds possess a substituted benzyl group at the 7-position, with a preference for steric bulk at the para position of the benzene ring. The most potent enzyme inhibitor (18t, IC50 = 3.0 nM) is approximately 3-fold more potent than lovastatin sodium salt (2). The most potent cholesterol biosynthesis inhibitor in HEP-G2 cells (18q, IC50 = 0.078 muM) is slightly less potent than 2 (sodium salt). Molecular modeling studies suggested that, when compared to the parent compound (18b) lacking the appropriate 7-substituent, 18t overlaps better with 2 and literature inhibitors 5 and 6 in a hydrophobic binding region adjacent to the enzyme active site.

  DOI：

  10.1021/jm00075a024

文献信息

• US5387693A
  申请人：——

  公开号：US5387693A

  公开（公告）日：1995-02-07