17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-bis-tert-butoxycarbonyl-(N'-4-nitrobenzyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan | 641611-46-3

• 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-didehydro-4,5α-epoxy-5'-bis-tert-butoxycarbonyl-(N'-4-nitrobenzyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan
• 英文别名: tert-butyl N-[N'-[(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]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-[(4-nitrophenyl)methyl]carbamate
• CAS: 641611-46-3
• 化学式: C₄₄H₅₀N₆O₉
• 分子量: 806.916
• InChiKey: LACNTGSJDJRWQM-NJUVABRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  59
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-bis-tert-butoxycarbonyl-(N'-4-nitrobenzyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan 在 镍 三乙胺 、 环己烯 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以63%的产率得到17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-bis-tert-butoxycarbonyl-(N'-4-aminobenzyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan
  参考文献：
  名称：

  Guanidino N-Substituted and N,N-Disubstituted Derivatives of the κ-Opioid Antagonist GNTI

  摘要：

  Derivatives of the highly selective kappa-opioid receptor antagonist GNTI (2a) have been prepared. Binding and functional studies conducted on cloned human opioid receptors expressed in Chinese hamster ovarian (CHO) cells suggested that adding a benzyl or a substituted benzyl group to the guanidino moiety led, in general, to a retention of high kappa-affinity and antagonist potency. Disubstitution of the guanidino moiety led to reduced kappa-selectivity.

  DOI：

  10.1021/jm0309203
• 作为产物：
  描述：

  N,N'-bis-Boc-S-methyl-isothiourea 在 sodium hydride 、 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-bis-tert-butoxycarbonyl-(N'-4-nitrobenzyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan
  参考文献：
  名称：

  Guanidino N-Substituted and N,N-Disubstituted Derivatives of the κ-Opioid Antagonist GNTI

  摘要：

  Derivatives of the highly selective kappa-opioid receptor antagonist GNTI (2a) have been prepared. Binding and functional studies conducted on cloned human opioid receptors expressed in Chinese hamster ovarian (CHO) cells suggested that adding a benzyl or a substituted benzyl group to the guanidino moiety led, in general, to a retention of high kappa-affinity and antagonist potency. Disubstitution of the guanidino moiety led to reduced kappa-selectivity.

  DOI：

  10.1021/jm0309203

文献信息

• Guanidino N-Substituted and N,N-Disubstituted Derivatives of the κ-Opioid Antagonist GNTI
  作者：Shannon L. Black、Cedric Chauvignac、Peter Grundt、Carl N. Miller、Susan Wood、John R. Traynor、John W. Lewis、Stephen M. Husbands

  DOI：10.1021/jm0309203

  日期：2003.12.1

  Derivatives of the highly selective kappa-opioid receptor antagonist GNTI (2a) have been prepared. Binding and functional studies conducted on cloned human opioid receptors expressed in Chinese hamster ovarian (CHO) cells suggested that adding a benzyl or a substituted benzyl group to the guanidino moiety led, in general, to a retention of high kappa-affinity and antagonist potency. Disubstitution of the guanidino moiety led to reduced kappa-selectivity.