17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-[(N-pentylamidino)ethyl]-3,14-dihydroxyindolo[2',3':6,7]morphinan

• 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-didehydro-4,5α-epoxy-5'-[(N-pentylamidino)ethyl]-3,14-dihydroxyindolo[2',3':6,7]morphinan
• 英文别名: N'-[2-[(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)-heptaen-7-yl]ethyl]pentanimidamide
• 化学式: C₃₃H₄₀N₄O₃
• 分子量: 540.706
• InChiKey: UAIUAJRUOCAUGH-RVLOQZQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  纳曲酮 在 镍 氨 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 49.5h， 生成 17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-[(N-pentylamidino)ethyl]-3,14-dihydroxyindolo[2',3':6,7]morphinan
  参考文献：
  名称：

  Selective κ-opioid antagonists related to naltrindole. effect of side-chain spacer in the 5′-amidinoalkyl series

  摘要：

  The study of kappa -opioid receptor function in vivo has been hampered by the limited choice of selective kappa -antagonists. Recently discovered cc-antagonists have not yet been utilised in vivo. We here report the synthesis and in vitro evaluation of a new amidine derivative of naltrindole. It showed substantially greater kappa -selectivity in binding assays than known analogues with shorter spacer in the amidine side chain. This indicates that in nor-BNI and related selective kappa -antagonists, the second basic centre may not be ideally located. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00433-9

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.
• Selective κ-opioid antagonists related to naltrindole. effect of side-chain spacer in the 5′-amidinoalkyl series
  作者：Andrew R Jales、Stephen M Husbands、John W Lewis

  DOI：10.1016/s0960-894x(00)00433-9

  日期：2000.10

  The study of kappa -opioid receptor function in vivo has been hampered by the limited choice of selective kappa -antagonists. Recently discovered cc-antagonists have not yet been utilised in vivo. We here report the synthesis and in vitro evaluation of a new amidine derivative of naltrindole. It showed substantially greater kappa -selectivity in binding assays than known analogues with shorter spacer in the amidine side chain. This indicates that in nor-BNI and related selective kappa -antagonists, the second basic centre may not be ideally located. (C) 2000 Elsevier Science Ltd. All rights reserved.