17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-(1'-ethyl)-indolomorphinan

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-(1'-ethyl)-indolomorphinan
• 英文别名: (1S,2S,13R,21R)-22-(cyclopropylmethyl)-11-ethyl-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaene-2,16-diol
• 化学式: C₂₈H₃₀N₂O₃
• 分子量: 442.558
• InChiKey: CMWRRNPRWLSKFN-CSZVXOJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  盐酸纳曲酮 在 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、34.48 kPa 条件下， 反应 3.0h， 生成 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-(1'-ethyl)-indolomorphinan
  参考文献：
  名称：

  Synthesis of tritiated N1′-alkyl derivatives of the delta opioid receptor ligand naltrindole

  摘要：

  Tritiated N1'-methyI and N1'-ethyl analogues of naltrindole (NTI) have been synthesized for evaluation as radioligands for studies of delta opioid receptors. The two N1'-alkyl-5',7'-dibromoNTI precursors for radiolabeling were prepared by base-promoted alkylation of 2,4-dibromophenylhydrazine with either iodomethane or iodoethane followed by condensation with naltrexone using the Fischer indole synthesis. Catalytic debromotritiation followed by HPLC purification afforded [H-3]MeNTI (17.3 Ci/mmol) and [H-3]EtNTI (22.5 Ci/mmol)with high chemical and radiochemical purities (greater than or equal to 99.8%).

  DOI：

  10.1002/(sici)1099-1344(199702)39:2<115::aid-jlcr947>3.0.co;2-3

文献信息

• Selective δ-opioid receptor ligands: potential PET ligands based on naltrindole
  作者：Joanne Clayson、Andrew Jales、Robin J Tyacke、Alan L Hudson、David J Nutt、John W Lewis、Stephen M Husbands

  DOI：10.1016/s0960-894x(01)00112-3

  日期：2001.4

  Two series of delta -selective ligands related to the prototypic delta -antagonist naltrindole have been prepared and evaluated in opioid binding assays with the aim of developing new PET ligands for the delta -opioid receptor. One compound (5d) had significantly here selectivity than naltrindole, but with substantially reduced binding affinity. For those compounds retaining similar affinity to naltrindole. those having ethyl and fluoroethyl substituents afforded the highest levels of selectivity. However, none of the compounds combined the high level of affinity and selectivity ideally suited to the development of an imaging agent. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of tritiated N1′-alkyl derivatives of the delta opioid receptor ligand naltrindole
  作者：John R. Lever、Suzanne M. Johnson

  DOI：10.1002/(sici)1099-1344(199702)39:2<115::aid-jlcr947>3.0.co;2-3

  日期：1997.2

  Tritiated N1'-methyI and N1'-ethyl analogues of naltrindole (NTI) have been synthesized for evaluation as radioligands for studies of delta opioid receptors. The two N1'-alkyl-5',7'-dibromoNTI precursors for radiolabeling were prepared by base-promoted alkylation of 2,4-dibromophenylhydrazine with either iodomethane or iodoethane followed by condensation with naltrexone using the Fischer indole synthesis. Catalytic debromotritiation followed by HPLC purification afforded [H-3]MeNTI (17.3 Ci/mmol) and [H-3]EtNTI (22.5 Ci/mmol)with high chemical and radiochemical purities (greater than or equal to 99.8%).