17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-5',7'-dibromo-6,7-2',3'-(1'-ethyl)-indolomorphinan | 188258-73-3

• 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-5',7'-dibromo-6,7-2',3'-(1'-ethyl)-indolomorphinan
• 英文别名: (1S,2S,13R,21R)-7,9-dibromo-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(10),6,8,15,17,19(25)-heptaene-2,16-diol
• CAS: 188258-73-3
• 化学式: C₂₈H₂₈Br₂N₂O₃
• 分子量: 600.35
• InChiKey: NHRJLLKBHSLUHM-OZBXUNDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 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

• 作为反应物：
  描述：

  17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-5',7'-dibromo-6,7-2',3'-(1'-ethyl)-indolomorphinan 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以95%的产率得到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
• 作为产物：
  描述：

  盐酸纳曲酮 、 N-ethyl-2,4-dibromophenylhydrazine hydrochloride 在 盐酸 、 溶剂黄146 作用下， 反应 1.0h， 以13%的产率得到17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-5',7'-dibromo-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

• 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%).