acyclovir propionate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: acyclovir propionate
• 英文别名: 9-(2-propionoxyethoxy)methylguanine；9-(2-propionyloxyethoxymethyl)guanine；9-(2-Propionyloxyethoxymethyl)guanine；2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl propanoate
• 化学式: C₁₁H₁₅N₅O₄
• 分子量: 281.271
• InChiKey: JGSACAANCVVBKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  阿昔洛韦 在 吡啶 作用下， 以 N-甲基乙酰胺 、 丙酸酐 为溶剂， 生成 acyclovir propionate
  参考文献：
  名称：

  2-Amido-9-(2-acyloxyethoxymethyl)hypoxanthines

  摘要：

  制备9-(2-羟乙氧甲基)鸟嘌呤的方法包括制备化合物##STR1##其中R和R.sup.1为氢、低碳烷基和苯基，然后水解。9-(2-羟乙氧甲基)鸟嘌呤可用作抗病毒药物。

  公开号：

  US04146715A1

文献信息

• Preparation of N-9 substituted guanine compounds
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05565565A1

  公开（公告）日：1996-10-15

  The invention relates to efficient and selective processes for the synthesis of the antiviral N-9 substituted guanine compounds acyclovir and ganciclovir.

  这项发明涉及一种高效且选择性的合成抗病毒N-9取代鸟苷化合物阿昔洛韦和甘氨酸胞苷的过程。
• Purine derivatives
  申请人：Burroughs Wellcome Co.

  公开号：US04287188A1

  公开（公告）日：1981-09-01

  9-(2-Hydroxyethoxymethyl) (and related) derivatives of certain 6-, and 2,6-substituted purines have been discovered to have potent anti-viral activities. Novel compounds and their pharamceutically acceptable salts, pharmaceutical formulations containing the compounds of this invention, and the treatment of viral infections with these formulations are all disclosed. 9-(2-Hydroxyethoxymethyl)guanine and 2-amino-9-(2-hydroxyethoxymethyl) adenine are examples of especially active compounds of this invention. Also preferred because of its high oral absorption is the phosphate and especially the monophosphate of 9-(2-hydroxyethoxymethyl)guanine as well as pharmaceutically acceptable salts thereof.

  已发现某些6-和2,6-取代嘌呤的9-(2-羟乙氧甲基)(及相关)衍生物具有强效的抗病毒活性。本发明揭示了新的化合物及其药学上可接受的盐、含有本发明化合物的制剂以及使用这些制剂治疗病毒感染。9-(2-羟乙氧甲基)鸟嘌呤和2-氨基-9-(2-羟乙氧甲基)腺嘌呤是本发明中特别活性的化合物的例子。另外，由于其高口服吸收性，9-(2-羟乙氧甲基)鸟嘌呤的磷酸盐，特别是单磷酸盐及其药学上可接受的盐也是首选。
• Adenine derivatives
  申请人：Burroughs Wellcome Co.

  公开号：US04323573A1

  公开（公告）日：1982-04-06

  Novel 2-amino substituted adenine compounds and their use as antiviral compounds are disclosed. In particular the compound 2-amino-9-(2-hydroxyethoxymethyl) adenine is particularly advantageous as an antiviral in that it has high oral absorption and that upon metabolism in mammals, it has the property of being converted to 9-(2-hydroxyethoxymethyl) guanine which is also a highly active antiviral.

  本发明揭示了新型2-氨基取代腺嘌呤化合物及其作为抗病毒化合物的用途。特别是化合物2-氨基-9-(2-羟乙氧甲基)腺嘌呤具有高口服吸收性能，在哺乳动物体内代谢后，具有被转化为9-(2-羟乙氧甲基)鸟嘌呤的性质，后者同样是一种高度活跃的抗病毒化合物，因此该化合物在抗病毒方面具有特别的优势。
• COMPOSITIONS AND METHODS FOR ENHANCING DRUG DELIVERY ACROSS AND INTO EPITHELIAL TISSUES
  申请人：Rothbard Jonathan B.

  公开号：US20110206610A1

  公开（公告）日：2011-08-25

  This invention provides compositions and methods for enhancing delivery of drugs and other agents across epithelial tissues, including the skin, gastrointestinal tract, pulmonary epithelium, ocular tissues and the like. The compositions and methods are also useful for delivery across endothelial tissues, including the blood brain barrier. The compositions and methods employ a delivery enhancing transporter that has sufficient guanidino or amidino sidechain moieties to enhance delivery of a compound conjugated to the reagent across one or more layers of the tissue, compared to the non-conjugated compound. The delivery-enhancing polymers include, for example, poly-arginine molecules that are preferably between about 6 and 25 residues in length.

  本发明提供了用于增强药物和其他药剂通过上皮组织的传递的组合物和方法，包括皮肤、胃肠道、肺上皮、眼组织等。这些组合物和方法也适用于通过内皮组织的传递，包括血脑屏障。这些组合物和方法采用了一种传递增强转运体，该转运体具有足够的鸟氨酸或酰胺基侧链基团，以增强与试剂结合的化合物通过一层或多层组织的传递，相对于未结合的化合物。传递增强聚合物包括例如，长度在6到25个残基之间的多鸟氨酸分子。
• ——
  作者：Hiroto Bando、Toshihide Takagi、Fumiyoshi Yamashita、Yoshinobu Takakura、Mitsuru Hashida

  DOI：10.1023/a:1016000827719

  日期：——

  Purpose. A theoretical design of percutaneous penetration enhancement in which prodrug derivation and enhancer application are combined is proposed based on the skin diffusion model and it is experimentally verified.Methods. Employing acyclovir as a model drug, the hypothesis was tested by synthesis of its prodrugs and evaluation of their in vitro permeation in the rat skin, with or without a penetration enhancer, 1-geranylazacycloheptan-2-one(GACH).Results. Among five acyclovir prodrugs, those with higher lipophilicities (propionate, butyrate, valerate, and hexanoate prodrugs) showed greater skin penetration than those of hydrophilic prodrugs (acetate), when administered in combination with GACH. Furthermore, the observed enhancement ratios were in good agreement with those predicted by theoretical consideration.Conclusions. Thus, skin permeation of prodrugs applied with an enhancer can be predicted and optimized by model analysis.