5'-carboxy-17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-3,14-dihydroxy-indolo[2',3':6,7]morphinan | 496848-18-1

• 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: 5'-carboxy-17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-3,14-dihydroxy-indolo[2',3':6,7]morphinan
• 英文别名: (1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-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-7-carboxylic acid
• CAS: 496848-18-1
• 化学式: C₂₇H₂₆N₂O₅
• 分子量: 458.514
• InChiKey: GHPXKKQGBLVNIO-GYHUNEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-carboxy-17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-3,14-dihydroxy-indolo[2',3':6,7]morphinan 在 4-(4-formyl-3-methoxyphenoxy)butyrylaminomethylpolystyrene 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成
  参考文献：
  名称：

  Affinity identification of δ-opioid receptors using latex nanoparticles

  摘要：

  Three types of latex nanoparticles carrying naltrindole (NTI) derivatives were synthesized as probes for the affinity isolation of their binding proteins including the delta-opioid receptor. The effect of the attachment of NTI to different positions on the linker was investigated. Only latex nanoparticles in which the NTI derivative was linked through the phenol group were useful for isolating the recombinant delta-opioid receptor solubilized from CHO cell membrane. These latex nanoparticles could be a useful tool for investigations of the pharmacological activity of NTI. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.028
• 作为产物：
  描述：

  纳曲酮 、 4-肼基苯甲酸 在 溶剂黄146 作用下， 反应 5.0h， 以12%的产率得到5'-carboxy-17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-3,14-dihydroxy-indolo[2',3':6,7]morphinan
  参考文献：
  名称：

  Affinity identification of δ-opioid receptors using latex nanoparticles

  摘要：

  Three types of latex nanoparticles carrying naltrindole (NTI) derivatives were synthesized as probes for the affinity isolation of their binding proteins including the delta-opioid receptor. The effect of the attachment of NTI to different positions on the linker was investigated. Only latex nanoparticles in which the NTI derivative was linked through the phenol group were useful for isolating the recombinant delta-opioid receptor solubilized from CHO cell membrane. These latex nanoparticles could be a useful tool for investigations of the pharmacological activity of NTI. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.028

文献信息

• The Role of the Side Chain in Determining Relative δ- and κ-Affinity in C5‘-Substituted Analogues of Naltrindole
  作者：Shannon L. Black、Andrew R. Jales、Wolfgang Brandt、John W. Lewis、Stephen M. Husbands

  DOI：10.1021/jm020997b

  日期：2003.1.1

  The role of the side chain in 5'-substituted analogues of naltrindole has been further explored with the synthesis of series of amides, amidines, and ureas. Amidines (8, 13) had greatest selectivity for the kappa receptor, as predicted from consideration of the message-address concept. It was also found that an appropriately located carbonyl group, in ureas (10) and amides (7), led to retention of affinity and antagonist potency at the 6 receptor.