(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (S)-1-(nicotinoyl-L-prolyl-L-prolyl-L-glutaminyl-L-leucyl)piperidine-2-carboxylate | 289046-15-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (S)-1-(nicotinoyl-L-prolyl-L-prolyl-L-glutaminyl-L-leucyl)piperidine-2-carboxylate
• CAS: 289046-15-7
• 化学式: C₆₀H₉₁N₇O₈
• 分子量: 1038.42
• InChiKey: CTGKRQBHMRKZIB-DATUUXHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  75.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  201.41
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (S)-1-(nicotinoyl-L-prolyl-L-prolyl-L-glutaminyl-L-leucyl)piperidine-2-carboxylate 、 碘甲烷 以 氯仿 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Brain-targeted chemical delivery of [Leu 2 , Pip 3 ]-TRH

  摘要：

  A chemical targeting system for [Leu(2), Pip(3)]-TRH (Gln,Leu,Pip) was synthesized in order to allow its specific delivery to the central nervous system (CNS). Sequential metabolism of the obtained 'packaged' chemical delivery system, (CDS), DHT-Pro-Pro-Gln-Leu-Pip-OCh, should yield a 'locked-in' precursor following the oxidative conversion of the dihydrotrigonellyl (DHT) to the trigonellyl (T+) moiety, followed by removal of the cholesteryl function and cleavage of the T+-Pro-Pro by prolyl endopeptidase. The antagonism of barbiturate-induced sleeping time was used to assess the activity of the CDS. The sleeping time after administration of vehicle and [Leu(2)]-TRH was 100.5 +/- 6.3 min, and 78.2 +/- 4.7 min, respectively. The [Leu(2), Pip(3)]-TRH-CDS showed a significant decrease in sleeping time (58.2 +/- 3.4 min) compared to the vehicle or [Leu(2)]-TRH. These results indicate successful brain delivery of the precursor construct, and an effective release of the active GlnLeuPip in the brain. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00043-2
• 作为产物：
  描述：

  (S)-Piperidine-1,2-dicarboxylic acid 2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] ester 1-(9H-fluoren-9-ylmethyl) ester 在 哌啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (S)-1-(nicotinoyl-L-prolyl-L-prolyl-L-glutaminyl-L-leucyl)piperidine-2-carboxylate
  参考文献：
  名称：

  Brain-targeted chemical delivery of [Leu 2 , Pip 3 ]-TRH

  摘要：

  A chemical targeting system for [Leu(2), Pip(3)]-TRH (Gln,Leu,Pip) was synthesized in order to allow its specific delivery to the central nervous system (CNS). Sequential metabolism of the obtained 'packaged' chemical delivery system, (CDS), DHT-Pro-Pro-Gln-Leu-Pip-OCh, should yield a 'locked-in' precursor following the oxidative conversion of the dihydrotrigonellyl (DHT) to the trigonellyl (T+) moiety, followed by removal of the cholesteryl function and cleavage of the T+-Pro-Pro by prolyl endopeptidase. The antagonism of barbiturate-induced sleeping time was used to assess the activity of the CDS. The sleeping time after administration of vehicle and [Leu(2)]-TRH was 100.5 +/- 6.3 min, and 78.2 +/- 4.7 min, respectively. The [Leu(2), Pip(3)]-TRH-CDS showed a significant decrease in sleeping time (58.2 +/- 3.4 min) compared to the vehicle or [Leu(2)]-TRH. These results indicate successful brain delivery of the precursor construct, and an effective release of the active GlnLeuPip in the brain. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00043-2

文献信息

• Bodor, Pharmazie, 2000, vol. 55, # 3, p. 163 - 166
  作者：Bodor

  DOI：——

  日期：——