1'-(p-aminobenzyl)-17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,14-dihydroxyindolo<2',3':6,7>morphinan | 155512-43-9

• 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: 1'-(p-aminobenzyl)-17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,14-dihydroxyindolo<2',3':6,7>morphinan
• 英文别名: (1S,2S,13R,21R)-11-[(4-aminophenyl)methyl]-22-(cyclopropylmethyl)-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
• CAS: 155512-43-9
• 化学式: C₃₃H₃₃N₃O₃
• 分子量: 519.643
• InChiKey: HNYRFIBNOUYLCL-OUDZLNJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  83.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1'-(p-aminobenzyl)-17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,14-dihydroxyindolo<2',3':6,7>morphinan 、 (benzotriazol-1-yloxy)acetic acid 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(benzotriazol-1-yloxy)-N-[4-[[(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),5,7,9,15,17,19(25)-heptaen-11-yl]methyl]phenyl]acetamide
  参考文献：
  名称：

  Korlipara; Takemori; Portoghese, Journal of Medicinal Chemistry, 1995, vol. 38, # 8, p. 1337 - 1343

  摘要：

  DOI：
• 作为产物：
  描述：

  17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,14-dihydroxy-1'-(p-nitrobenzyl)indolo<2',3':6,7>morphinan 在 盐酸 、 tin 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以59%的产率得到1'-(p-aminobenzyl)-17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,14-dihydroxyindolo<2',3':6,7>morphinan
  参考文献：
  名称：

  N-Benzylnaltrindoles as Long-Acting .delta.-Opioid Receptor Antagonists

  摘要：

  The indolic nitrogen of the delta-opioid receptor antagonist, naltrindole (1), was derivatized with benzyl or substituted benzyl to afford a series (2-9) that retained delta-opioid receptor antagonist activity and selectivity in vitro. The two most potent members (2 and 8) of the series were evaluated in mice and were found to produce delta-selective antagonism of [D-Ser(2),Leu(5)] enkephalin-Thr(6) which lasted 5 days. N-Benzylnaltrindole (2) should be useful as a delta(2)-selective antagonist for in vivo studies where prolonged action is desired.

  DOI：

  10.1021/jm00038a018

文献信息

• N-Benzylnaltrindoles as Long-Acting .delta.-Opioid Receptor Antagonists
  作者：V. L. Korlipara、A. E. Takemori、P. S. Portoghese

  DOI：10.1021/jm00038a018

  日期：1994.6

  The indolic nitrogen of the delta-opioid receptor antagonist, naltrindole (1), was derivatized with benzyl or substituted benzyl to afford a series (2-9) that retained delta-opioid receptor antagonist activity and selectivity in vitro. The two most potent members (2 and 8) of the series were evaluated in mice and were found to produce delta-selective antagonism of [D-Ser(2),Leu(5)] enkephalin-Thr(6) which lasted 5 days. N-Benzylnaltrindole (2) should be useful as a delta(2)-selective antagonist for in vivo studies where prolonged action is desired.
• Korlipara; Takemori; Portoghese, Journal of Medicinal Chemistry, 1995, vol. 38, # 8, p. 1337 - 1343
  作者：Korlipara、Takemori、Portoghese

  DOI：——

  日期：——