N6-丙酰虫草素 | 77378-04-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N6-丙酰虫草素
• 英文名称: N-propionyl-cordycepin
• 英文别名: N6-Propionyl Cordycepin；N-[9-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]propanamide
• CAS: 77378-04-2
• 化学式: C₁₃H₁₇N₅O₄
• 分子量: 307.309
• InChiKey: SPRCIUDOEWOPKD-HHURGBBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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 、 丙酰氯 在 吡啶 作用下， 以75.5%的产率得到N6-丙酰虫草素
  参考文献：
  名称：

  Synthesis and pharmacokinetic evaluation of novel N-acyl-cordycepin derivatives with a normal alkyl chain

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2008.05.013

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.