trans-2-pyrrolidinyl-3-(N-methyl-3',4'-dichlorobenzamido)-1,2,3,4-tetrahydronaphthalene | 115904-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-2-pyrrolidinyl-3-(N-methyl-3',4'-dichlorobenzamido)-1,2,3,4-tetrahydronaphthalene
• 英文别名: 3,4-dichloro-N-methyl-N-[(2S,3S)-3-pyrrolidin-1-yl-1,2,3,4-tetrahydronaphthalen-2-yl]benzamide
• CAS: 115904-97-7；133970-02-2；136908-72-0
• 化学式: C₂₂H₂₄Cl₂N₂O
• 分子量: 403.351
• InChiKey: GMXYALWRCZHEEM-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  trans-2-hydroxy-3-pyrrolidinyl-1,2,3,4-tetrahydronaphthalene 在 甲基磺酰氯 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 37.5h， 生成 trans-2-pyrrolidinyl-3-(N-methyl-3',4'-dichlorobenzamido)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Naphtho and benzo analogs of the .kappa. opioid agonist trans-(.+-.)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide

  摘要：

  Further elaboration on the structure-activity relationships in our U-50,488 series has revealed that benzologation of this cyclohexane-1,2-diamine derivative provides compounds which either maintain the interaction with the kappa-receptor (e.g. compounds 3a and 5a in the phenylacetamido series) or eliminate the mu-receptor mediated analgesia (e.g. compounds 3-6 in the benzamido series). Naphthologation also caused the elimination of mu-receptor mediated analgesia (e.g. compounds 17a and 17b).

  DOI：

  10.1021/jm00110a021

文献信息

• Benzo-fused cycloalkane and oxa- and thia-, cycloalkane trans-1,2-diamine derivatives
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0260555A1

  公开（公告）日：1988-03-23

  Benzo-fused cycloalkane and oxa-and thiacycloalkane trans-1,2-diamine compounds of the formula: or wherein A, B, C, D, n, X, Y, R, R1, R2 and R3 are as defined in the specification, e.g., trans-3,4-dichloro-N-methyl-N-[2-(pyrrolidin-1-yl)-5-methoxy-1,2,3,4-tetrahydronaphth-1-yl]benzeneacetamide, and the pharmaceutically acceptable salts or N-oxides thereof, are useful as analgesics and/or diuretics.

  式中 A、B、C、D、n、X、Y、R、R1、R2 和 R3 如说明书中所定义的苯并熔环烷烃和氧杂和硫杂环烷烃反式-1,2-二胺化合物，例如反式-3,4-二氯-N-甲基-N-[2-(吡咯烷-1-基)-5-甲氧基-1,2,3,4-四氢萘-1-基]苯乙酰胺及其药学上可接受的盐或 N-氧化物，可用作镇痛剂和/或利尿剂。
• US4876269A
  申请人：——

  公开号：US4876269A

  公开（公告）日：1989-10-24
• US5010085A
  申请人：——

  公开号：US5010085A

  公开（公告）日：1991-04-23
• US5043350A
  申请人：——

  公开号：US5043350A

  公开（公告）日：1991-08-27
• Naphtho and benzo analogs of the .kappa. opioid agonist trans-(.+-.)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide
  作者：Jeremiah P. Freeman、Eric T. Michalson、Stan V. D'Andrea、Lubomir Baczynskyj、Philip F. VonVoigtlander、R. A. Lahti、Martin W. Smith、Charles F. Lawson、Terrence A. Scahill

  DOI：10.1021/jm00110a021

  日期：1991.6

  Further elaboration on the structure-activity relationships in our U-50,488 series has revealed that benzologation of this cyclohexane-1,2-diamine derivative provides compounds which either maintain the interaction with the kappa-receptor (e.g. compounds 3a and 5a in the phenylacetamido series) or eliminate the mu-receptor mediated analgesia (e.g. compounds 3-6 in the benzamido series). Naphthologation also caused the elimination of mu-receptor mediated analgesia (e.g. compounds 17a and 17b).