6-fluoro-4-hydroxy-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)chroman-2-carboxylic acid | 1206912-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-fluoro-4-hydroxy-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)chroman-2-carboxylic acid
• 英文别名: 6-fluoro-4-hydroxy-8-(1,3,5-trimethylpyrazol-4-yl)-3,4-dihydro-2H-chromene-2-carboxylic acid
• CAS: 1206912-71-1
• 化学式: C₁₆H₁₇FN₂O₄
• 分子量: 320.32
• InChiKey: PKZDUQZRMKEVSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-fluoro-4-hydroxy-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)chroman-2-carboxylic acid 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 3.0h， 以55%的产率得到6-fluoro-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)chroman-2-carboxylic acid
  参考文献：
  名称：

  De Novo Design of a Picomolar Nonbasic 5-HT_1B Receptor Antagonist

  摘要：

  We describe herein the discovery of novel, de novo designed, 5-HT1B receptor antagonists that lack a basic moiety and that provide improved hERG and in vitro phospholipidosis profiles. We used a known 5-HT1B antagonist template as our starting point and focused on replacing the piperazine moiety. Pyrazole-based ideas were designed and synthesized among a small library of piperazine replacements. To our knowledge, these are the first potent, nonbasic, functionally active antagonists of the 5-HT1B receptor.

  DOI：

  10.1021/jm901200t
• 作为产物：
  描述：

  potassium 6-fluoro-4-oxo-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-chromene-2-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 异丙醇 为溶剂， 70.0 ℃ 、9.0 MPa 条件下， 以750 mg的产率得到6-fluoro-4-hydroxy-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)chroman-2-carboxylic acid
  参考文献：
  名称：

  De Novo Design of a Picomolar Nonbasic 5-HT_1B Receptor Antagonist

  摘要：

  We describe herein the discovery of novel, de novo designed, 5-HT1B receptor antagonists that lack a basic moiety and that provide improved hERG and in vitro phospholipidosis profiles. We used a known 5-HT1B antagonist template as our starting point and focused on replacing the piperazine moiety. Pyrazole-based ideas were designed and synthesized among a small library of piperazine replacements. To our knowledge, these are the first potent, nonbasic, functionally active antagonists of the 5-HT1B receptor.

  DOI：

  10.1021/jm901200t