6-hydroxynaphthalene-2-carboxylic acid {(1S)-1-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-trans-dimethyl-1-piperidinylmethyl]-2-methylpropyl}amide | 1234672-78-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-hydroxynaphthalene-2-carboxylic acid {(1S)-1-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-trans-dimethyl-1-piperidinylmethyl]-2-methylpropyl}amide
• 英文别名: 6-hydroxy-N-[(2S)-1-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]-3-methylbutan-2-yl]naphthalene-2-carboxamide
• CAS: 1234672-78-6
• 化学式: C₂₉H₃₆N₂O₃
• 分子量: 460.616
• InChiKey: YPKQMHKJOIWRQX-FCIAUAKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxynaphthalene-2-carboxylic acid {(1S)-1-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-trans-dimethyl-1-piperidinylmethyl]-2-methylpropyl}amide 在 盐酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成 6-hydroxynaphthalene-2-carboxylic acid {(1S)-1-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-trans-dimethyl-1-piperidinylmethyl]-2-methylpropyl}amide hydrochloride
  参考文献：
  名称：

  Analogues of (3R)-7-Hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in Vitro and in Vivo Opioid Receptor Antagonist Activity

  摘要：

  The synthesis of compounds 6, 7a,b, 8a,b, 9a,b, and 10a,b where the amino -NH- group of JDTic (3) was replaced with an aromatic =CH-, CH2, O, S, or SO group was accomplished and used to further characterize the SAR of the compound 3 class of kappa opioid receptor antagonists. All of the compounds showed subnanomolar to low nanomolar K-e values at the kappa opioid receptor. The most potent compound was 7a, where the amino -NH- group of 3 was replaced by a methylene (-CH2-) group. This compound had a K-e = 0.18 nM and was 37- and 248-fold selective for the kappa relative to the mu and delta opioid receptors, respectively. Similar to compound 3, compound 7a antagonized selective kappa agonist U50,488-induced diuresis after sc administration in rats. In contrast to 3, where kappa antagonist activity lasted for three weeks, compound 7a did not show any kappa antagonist activity after one week.

  DOI：

  10.1021/jm1004978
• 作为产物：
  描述：

  2-羟基-6-萘甲酸 、 3-[1-(2S-amino-3-methylbutyl)-3R,4R-dimethyl-4-piperidinyl]phenol 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 以0.095 g的产率得到6-hydroxynaphthalene-2-carboxylic acid {(1S)-1-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-trans-dimethyl-1-piperidinylmethyl]-2-methylpropyl}amide
  参考文献：
  名称：

  Analogues of (3R)-7-Hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in Vitro and in Vivo Opioid Receptor Antagonist Activity

  摘要：

  The synthesis of compounds 6, 7a,b, 8a,b, 9a,b, and 10a,b where the amino -NH- group of JDTic (3) was replaced with an aromatic =CH-, CH2, O, S, or SO group was accomplished and used to further characterize the SAR of the compound 3 class of kappa opioid receptor antagonists. All of the compounds showed subnanomolar to low nanomolar K-e values at the kappa opioid receptor. The most potent compound was 7a, where the amino -NH- group of 3 was replaced by a methylene (-CH2-) group. This compound had a K-e = 0.18 nM and was 37- and 248-fold selective for the kappa relative to the mu and delta opioid receptors, respectively. Similar to compound 3, compound 7a antagonized selective kappa agonist U50,488-induced diuresis after sc administration in rats. In contrast to 3, where kappa antagonist activity lasted for three weeks, compound 7a did not show any kappa antagonist activity after one week.

  DOI：

  10.1021/jm1004978