(+/-)-1,2,3,4-tetrahydro-8-methoxy-2-oxo-1-naphthalenecarboxylic acid methyl ester | 60683-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-1,2,3,4-tetrahydro-8-methoxy-2-oxo-1-naphthalenecarboxylic acid methyl ester
• 英文别名: Methyl-8-methoxy-2-oxotetralin-1-carboxylat；1,2,3,4-Tetrahydro-8-methoxy-2-oxo-1-naphthalene carboxylic acid methyl ester；methyl 8-methoxy-2-oxo-3,4-dihydro-1H-naphthalene-1-carboxylate
• CAS: 60683-74-1
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: HEABAIWNVBBYPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-1,2,3,4-tetrahydro-8-methoxy-2-oxo-1-naphthalenecarboxylic acid methyl ester 在 lithium chloride 、 lithium diisopropyl amide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 (+/-)-1,2,3,4-tetrahydro-8-methoxy-3-(2-propenyl)-2-oxonaphthalene
  参考文献：
  名称：

  Centrally acting serotonergic agents. Synthesis and structure-activity relationships of C-1- or C-3-substituted derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin

  摘要：

  The synthesis and structure-activity relationships (SAR) of C-1- or C-3-substituted derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) are described. These analogs were synthesized via alkylation of the tetralone derivatives followed by reductive amination. All of the analogs were inactive at the dopamine D2 receptor. Among the 8-OMe or 8-OH C-1,N-disubstituted analogs synthesized, the cis analogs were more potent in the 5-HT1A binding assay than the corresponding trans analogs. However, in the case of 1-(cyclopropylmethyl)-N-n-propyl analogs, the trans isomer has a slightly higher 5-HT1A affinity than its cis counterpart. The order of binding potency for C-1 substitution was found to be allyl > hydroxymethyl> n-propyl > cyclopropylmethyl much greater than carbomethoxy. Interestingly, the 5-OMe analogs were found to be inactive in both the 5-HT1A and dopamine D2 binding assays. In the C-3 allyl-substituted analogs, 5-HT1A agonist activity was found to be considerably lower. In these examples, the trans analogs showed weak 5-HT1A binding activity whereas the cis analogs were inactive. Analogs with C-1,N,N-trisubstitution also showed a marked decrease in 5-HT1A binding affinity. Overall, the SAR study showed that cis C-1 substitution maintains the 5-HT1A agonist activity of 8-OH-DPAT whereas trans C-1 substitution displays somewhat diminished activity. On the other hand, the trans C-3 substitution shows modest agonist activity whereas cis C-3 substitution removes the activity completely.

  DOI：

  10.1021/jm00058a003
• 作为产物：
  描述：

  8-甲氧基-3,4-二氢-1H-2-萘酮 、 碳酸二甲酯 在 盐酸 、 二异丙胺 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 以0.5 g (2%)的产率得到(+/-)-1,2,3,4-tetrahydro-8-methoxy-2-oxo-1-naphthalenecarboxylic acid methyl ester
  参考文献：
  名称：

  Therapeutically useful 2-aminotetralin derivatives

  摘要：

  这项发明是治疗有用的2-氨基四氢萘及其药用可接受的酸盐，其化学式为。这些化合物可用于治疗中枢神经系统疾病、高血压、糖尿病、性功能障碍以及控制食欲。

  公开号：

  US06331636B1

文献信息

• THERAPEUTICALLY USEFUL 2-AMINOTETRALIN DERIVATIVES
  申请人：THE UPJOHN COMPANY

  公开号：EP0476016A1

  公开（公告）日：1992-03-25
• (1,2N) AND (3,2N)-CARBOCYCLIC-2-AMINO TETRALIN DERIVATIVES
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0482084B1

  公开（公告）日：1997-05-07
• US5491236A
  申请人：——

  公开号：US5491236A

  公开（公告）日：1996-02-13
• US5545755A
  申请人：——

  公开号：US5545755A

  公开（公告）日：1996-08-13
• US6331636B1
  申请人：——

  公开号：US6331636B1

  公开（公告）日：2001-12-18