9-[2-((4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenoyloxy)ethoxymethyl]-2-amino-1,9-dihydro-6H-purin-6-one | 1201904-87-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9-[2-((4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenoyloxy)ethoxymethyl]-2-amino-1,9-dihydro-6H-purin-6-one
• 英文别名: (4E,8E,12E,16E)-2-((2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy)ethyl 4,8,13,17,21-pentamethyldocosa-4,8,12,16,20-pentaenoate；4'-trisnorsqualenoylacyclovir
• CAS: 1201904-87-1
• 化学式: C₃₅H₅₃N₅O₄
• 分子量: 607.837
• InChiKey: DPVPLNJFMQZQGB-CJJLVGFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  44.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  125.12
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 9-[2-((4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenoyloxy)ethoxymethyl]-2-amino-1,9-dihydro-6H-purin-6-one 在 水 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Solid-phase synthesis of an apoptosis-inducing tetrapeptide mimicking the Smac protein

  摘要：

  An approach for the solid-phase synthesis of apoptosis-inducing Smac peptidomimetics is presented. Using a Rink linker strategy, tetrapeptides mimicking the N-4-terminal residue of the Smac protein [(N-Me)AVPF sequence] were synthesized on PEGA resin in excellent purities and yields. Following two synthetic routes, a known tetrapeptide, incorporating a substituted proline, previously shown to exhibit excellent biological activity in vitro as well as low toxicity, was synthesized effectively on a solid support. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.028
• 作为产物：
  描述：

  阿昔洛韦 、 4,8,13,17,21-五甲基-4,8,12,16,20-二十二碳五烯酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以42%的产率得到9-[2-((4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenoyloxy)ethoxymethyl]-2-amino-1,9-dihydro-6H-purin-6-one
  参考文献：
  名称：

  Interaction of acyclovir and its squalenoyl–acyclovir prodrug with DMPC in monolayers at the air/water interface

  摘要：

  Acyclovir has been conjugated to the acyclic isoprenoid chain of squalene to form the squalenoyl-acyclovir prodrug. Its interaction with biomembrane models constituted by dimyristoyl phosphatidylcholine (DMPC) monolayers has been studied by employing the Langmuir-Blodgett technique. The aim of the work was to gain information on the interaction of these compounds with phospholipid membranes.DMPC/acyclovir or squalenoyl-acyclovir prodrug mixed monolayers have been prepared at increasing molar fractions of the compound and the isotherm mean molecular area/surface pressure has been registered at 10 and 37 degrees C. Results reveal that the squalenoyl moiety enhances the affinity of acyclovir for the biomembrane model. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2010.05.035

文献信息

• Nonpolymeric nanoassemblies for ocular administration of acyclovir: Pharmacokinetic evaluation in rabbits
  作者：Barbara Stella、Silvia Arpicco、Flavio Rocco、Susi Burgalassi、Nadia Nicosia、Silvia Tampucci、Patrizia Chetoni、Luigi Cattel

  DOI：10.1016/j.ejpb.2011.10.001

  日期：2012.1

  The aim of this study was to increase bioavailability of the antiviral drug acyclovir (ACV) when administered by the ocular route. For this purpose, a new lipophilic derivative of acyclovir was synthesized, both possessing greater lipophilicity and providing the formation of a homogeneous water dispersion with higher amount of ACV than the aqueous solution of the parent drug. This was done by chemically linking acyclovir to the isoprenoid chain of squalene, obtaining 4'-trisnorsqualenoylacyclovir (SQACV), in which squalene is covalently coupled to the 4'-hydroxy group of acyclovir. This new prodrug was then formulated as nonpolymeric nanoassemblies through nanoprecipitation; the resulting particles were characterized in terms of mean diameter, zeta potential, and stability. The pharmacokinetic profile of the prodrug in the tear fluid and in the aqueous humor of rabbits was evaluated and compared to that of the parent drug.Data showed that SQACV nanoassemblies increased the amount of ACV in the aqueous humor of rabbits compared to free ACV solution. This new amphiphilic prodrug of acyclovir is a very promising tool to increase the ocular bioavailability of the parent drug. (C) 2011 Elsevier B.V. All rights reserved.