N-octanoyl cordycepin | 77378-05-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N-octanoyl cordycepin
• 英文别名: 3'-Deoxy-N6-octanoyladenosine；N-[9-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]octanamide
• CAS: 77378-05-3
• 化学式: C₁₈H₂₇N₅O₄
• 分子量: 377.443
• InChiKey: QCOORYDEEUDEJJ-VEVIJQCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  虫草素 在 咪唑 、 四丁基氟化铵 、 1-羟基苯并三唑 、 1,2-二氯乙烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 N-octanoyl cordycepin
  参考文献：
  名称：

  WO2018133854A5

  摘要：

  公开号：

  WO2018133854A5

文献信息

• Synthesis and pharmacokinetic evaluation of novel N-acyl-cordycepin derivatives with a normal alkyl chain
  作者：H.-P. Wei、X.-L. Ye、Z. Chen、Y.-J. Zhong、P.-M. Li、S.-C. Pu、X.-G. Li

  DOI：10.1016/j.ejmech.2008.05.013

  日期：2009.2

  For slowing down the too fast metabolic velocity and increasing the bioavailability of cordycepin, four N-acyl-(propionyl-, octanoyl-, lauroyl- and stearoyl-) cordycepin derivatives were synthesized chemically and their pharmacokinetic profiles were investigated in this study. The results show that time of maximum concentration (T-max) and half-life (t(1/2)) would be elongated with the increase of the alkyl chain length, but maximum concentration (C-max) and area under concentration-time curve (AUC) increased initially, then decreased when the number of alkyl carbon exceeded eight. The T-max C-max and AUC of N-octanoyl-cordycepin were nearly 4, 30 and 68 times, respectively, higher than that of cordycepin. All derivatives could be transformed into cordycepin in vivo and the concentration of transformed cordycepin was proportional to that of derivatives. It indicated that N-octanoyl modification could decrease the metabolic velocity and increase the bioavailability of cordycepin to the maximum, thus it might be a promising prodrug of cordycepin. (C) 2008 Elsevier Masson SAS. All rights reserved.
• ADENOSINE ANALOG AND ITS USE IN REGULATING THE CIRCADIAN CLOCK
  申请人：NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING

  公开号：US20210338706A1

  公开（公告）日：2021-11-04

  The present invention provides a kind of nucleoside analogue compounds, and a composition comprising the compound and pentostatin, their use for modulating circadian rhythm, preferably, for shifting circadian phase, and methods for modulating circadian rhythm, preferably, for shifting circadian phase via the compound or the composition.
• [EN] ADENOSINE ANALOG AND ITS USE IN REGULATING THE CIRCADIAN CLOCK<br/>[FR] ANALOGUE D'ADÉNOSINE ET SON UTILISATION DANS LA RÉGULATION DE L'HORLOGE CIRCADIENNE
  申请人：NAT INSTITUTE OF BIOLOGICAL SCIENCES BEIJING

  公开号：WO2018133854A1

  公开（公告）日：2018-07-26

  Provided are a kind of nucleoside analogue compounds, and compositions comprising these compounds and pentostatin, their use for modulating circadian rhythm, preferably, for shifting circadian phase, and methods for modulating circadian rhythm, preferably, for shifting circadian phase via these compounds or the compositions.