17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-tert-butoxycarbonyl-(N',N''-dibutyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan | 641611-24-7

• 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'-tert-butoxycarbonyl-(N',N''-dibutyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan
• 英文别名: tert-butyl N-butyl-N-[N'-butyl-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]carbamimidoyl]carbamate
• CAS: 641611-24-7
• 化学式: C₄₀H₅₃N₅O₅
• 分子量: 683.891
• InChiKey: TXAPIOWNQKRAEV-DFQLMZRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-tert-butoxycarbonyl-(N',N''-dibutyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan 以 二氯甲烷 为溶剂， 反应 12.0h， 以86%的产率得到17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-(N',N''-dibutyl)guanidinyl-3,14-dihydroxyindolo[2',3':6,7]morphinan bis-trifluoroacetate
  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'-二正丁基硫脲 在 sodium hydride 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.17h， 生成 17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-5'-tert-butoxycarbonyl-(N',N''-dibutyl)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.