| 60332-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• CAS: 60332-36-7
• 化学式: C₁₉H₂₉NO
• 分子量: 287.445
• InChiKey: WIGCGAOCJNNKPT-MJXNMMHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 生成 3-(cyclopropylmethyl)-1,2,3,4,5,6,7,8,9,10-decahydro-cis-6,11-dimethyl-2,6-methano-3-benzazocin-8-one
  参考文献：
  名称：

  8-氨基-3-（环丙基甲基）-1,2,3,4,5,6-六氢-顺-6,11-二甲基-2,6-甲氨基-3-苯并佐辛的合成及药理作用。

  摘要：

  已制备了少量化合物1a，发现该化合物是一种具有麻醉-拮抗剂特性的强口服活性激动剂。1a是通过两种独立的途径制备的：（1）硝唑啉的硝化反应和随后的还原反应;（b）涉及将金属溶解的环唑嘌呤甲醚还原的顺序，然后进行氧化和Semmler-Wolff重排。制备并测试了几种类似物。

  DOI：

  10.1021/jm00175a013
• 作为产物：
  描述：

  Cyclazocine methyl ether 在 氨 、 sodium 、 异丙醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  8-氨基-3-（环丙基甲基）-1,2,3,4,5,6-六氢-顺-6,11-二甲基-2,6-甲氨基-3-苯并佐辛的合成及药理作用。

  摘要：

  已制备了少量化合物1a，发现该化合物是一种具有麻醉-拮抗剂特性的强口服活性激动剂。1a是通过两种独立的途径制备的：（1）硝唑啉的硝化反应和随后的还原反应;（b）涉及将金属溶解的环唑嘌呤甲醚还原的顺序，然后进行氧化和Semmler-Wolff重排。制备并测试了几种类似物。

  DOI：

  10.1021/jm00175a013

文献信息

• Syntheses and Opioid Receptor Binding Affinities of 8-Amino-2,6-methano-3-benzazocines
  作者：Mark P. Wentland、Yingchun Ye、Christopher L. Cioffi、Rongliang Lou、Qun Zhou、Guoyou Xu、Wenhu Duan、Christoph M. Dehnhardt、Xufeng Sun、Dana J. Cohen、Jean M. Bidlack

  DOI：10.1021/jm020429w

  日期：2003.2.1

  8-Amino-2,6-methano-3-benzazocine derivatives have been made using Pd-catalyzed amination procedures, and their affinities for opioid receptors were assessed. The 8-amino group was hypothesized to be a replacement for the prototypic 8-OH substituent for 2,6-methano-3-benzazocines and related opiates. This OH group is generally required for binding yet is implicated in unfavorable pharmacokinetic characteristics such as low oral bioavailability and rapid clearance via O-glucuronidation. The core structures in which the 8-OH group was replaced were cyclazocine and its enantiomers, ethylketocyclazocine and its enantiomers, ketocyclazocine, and Mr2034. Many new analogues had high affinity for opioid receptors with several in the subnanomolar range. Highest affinity was seen in analogues with secondary 8-(hetero)arylamino appendages. Binding to opioid receptors was enantioselective with the (2R,6R,11R)-configuration preferred and high selectivity for mu and kappa over delta opioid receptors was observed within the series. Several derivatives were shown to have intrinsic opioid-receptor-mediated activity in [S-35]GTPgammaS assays.
• 8-Aminocyclazocine analogues: synthesis and structure–activity relationships
  作者：Mark P Wentland、Guoyou Xu、Christopher L Cioffi、Yingchun Ye、Wenhu Duan、Dana J Cohen、Ann M Colasurdo、Jean M Bidlack

  DOI：10.1016/s0960-894x(99)00670-8

  日期：2000.1

  Opioid binding affinities were assessed for a series of cyclazocine analogues where the prototypic S-OH substituent of cyclazocine was replaced by amino and substituted-amino groups. For mu and kappa opioid receptors, secondary amine derivatives having the (2R,6R,11R)-configuration had the highest affinity. Most targets were efficiently synthesized from the triflate of cyclazocine or its enantiomers using Pd-catalyzed amination procedures. (C) 2000 Elsevier Science Ltd. All rights reserved.