(R)-5-Methoxy-1,2,3,4-tetrahydronapthalene-1-carboxylic acid (R)-dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone ester | 152148-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-5-Methoxy-1,2,3,4-tetrahydronapthalene-1-carboxylic acid (R)-dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone ester
• 英文别名: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1R)-5-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate
• CAS: 152148-47-5
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: JUXGSWJGRMPSNX-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-5-Methoxy-1,2,3,4-tetrahydronapthalene-1-carboxylic acid (R)-dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone ester 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 1-[(1R)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-N-methylmethanamine
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m
• 作为产物：
  描述：

  5-甲氧基-3,4-二氢-2H-1-萘酮 在 氢氧化钾 、 sodium tetrahydroborate 、 草酰氯 、 二甲基十二/十四烷基叔胺 、 锂丁酯 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙二醇 、 苯 为溶剂， 反应 29.75h， 生成 (R)-5-Methoxy-1,2,3,4-tetrahydronapthalene-1-carboxylic acid (R)-dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone ester
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m

文献信息

• Tertiary and secondary amines as alpha-2 antagonists and serotonin
  申请人：Abbott Laboratories

  公开号：US05288749A1

  公开（公告）日：1994-02-22

  The present invention provides tertiary and secondary amine compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof which are antagonists for alpha-2 adrenoreceptors and which inhibit serotonin (5-hydroxytryptamine, 5-HT) uptake.

  本发明提供了公式##STR1##的三级和二级胺化合物及其药用盐，这些化合物是α-2肾上腺素受体拮抗剂，可以抑制血清素（5-羟色胺，5-HT）的摄取。