(S)-(+)-8-fluoro-5-methoxychroman-3-amine | 1073593-00-6

• 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: (S)-(+)-8-fluoro-5-methoxychroman-3-amine
• 英文别名: (S)-(8-fluoro-5-methoxy-3,4-dihydro-2H-chromen-3-yl)amine；(3S)-8-fluoro-5-methoxy-3,4-dihydro-2H-chromen-3-amine
• CAS: 1073593-00-6
• 化学式: C₁₀H₁₂FNO₂
• 分子量: 197.209
• InChiKey: WZOULZLGSKBYTD-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-8-fluoro-5-methoxychroman-3-amine 、 3-(5-fluoro-1H-indol-3-yl)propanal 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (S)-8-fluoro-N-[3-(5-fluoro-1H-indol-3-yl)propyl]-5-methoxychroman-3-amine
  参考文献：
  名称：

  Advances toward New Antidepressants with Dual Serotonin Transporter and 5-HT_1A Receptor Affinity within a Class of 3-Aminochroman Derivatives. Part 2

  摘要：

  Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through,a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affinity at both the 5-HT reuptake site and the 5-HT1A receptor. Compounds of most interest were found to have a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran linked to a 3-alkylindole (straight chain), more specifically substituted with a 5-fluoro ((R)-(-)-35c), 5-cyano ((-)-52a), or 5,7-difluoro ((-)-52g). Several factors contributed to 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonism in vitro. Although most of our analogues showed good to excellent affinities at both targets, specific features such as cyclobutyl substitution on the basic nitrogen and stereochemistry at the 3-position of the chroman moiety seemed necessary for antagonism at the 5-HT1A receptor. Branched linkers seemed to impart antagonism even as racemates, however, potency of these analogues in the functional assay was not desirable enough to further pursue these compounds.

  DOI：

  10.1021/jm8007097
• 作为产物：
  描述：

  8-fluoro-5-methoxychroman-3-amine 生成 (R)-3-amino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran 、 (S)-(+)-8-fluoro-5-methoxychroman-3-amine
  参考文献：
  名称：

  [EN] 3-AMINO CHOMAN AND 2-AMINO TETRALIN DERIVATIVES
  [FR] DERIVES 3-AMINO CHOMANE ET 2-AMINO TETRALINE

  摘要：

  揭示了3-氨基色苷和2-氨基四氢萘衍生物以及含有这些化合物的组合物。还揭示了在治疗血清素失调症，如抑郁症和焦虑症中使用3-氨基色苷和2-氨基四氢萘化合物以及含有这些化合物的组合物的方法。

  公开号：

  WO2005012291A1