(+/-)-1-(acetoxymethoxy)-2,3-diacetoxypropane | 86357-10-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (+/-)-1-(acetoxymethoxy)-2,3-diacetoxypropane
• 英文别名: acetoxymethyl 2,3-diacetoxy-1-propyl ether；1,2-Propanediol, 3-[(acetyloxy)methoxy]-, 1,2-diacetate；[2-acetyloxy-3-(acetyloxymethoxy)propyl] acetate
• CAS: 86357-10-0
• 化学式: C₁₀H₁₆O₇
• 分子量: 248.233
• InChiKey: ZHAOLTOQGBUEET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,9-二乙酰鸟嘌呤 、 (+/-)-1-(acetoxymethoxy)-2,3-diacetoxypropane 生成 更昔洛韦杂质11
  参考文献：
  名称：

  ASHTON, WALLACE T.;FIELD, ARTHUR K.;KARKAS, JOHN D.;TOLMAN, RICHARD L.

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸酐 、 alkaline earth salt of/the/ methylsulfuric acid 在 溶剂黄146 、 zinc(II) chloride 作用下， 反应 4.5h， 以34%的产率得到(+/-)-1-(acetoxymethoxy)-2,3-diacetoxypropane
  参考文献：
  名称：

  （S）-，（R）-和（+/-）-9-[（2,3-二羟基-1-丙氧基）甲基]鸟嘌呤，2'-nor-2'的线性异构体的合成和抗疱疹活性-脱氧鸟苷。

  摘要：

  外消旋9-[（（2,3-二羟基-1-丙氧基）甲基]鸟嘌呤[（+/-）-iNDG]，无环鸟苷（ACV）的新类似物和2'-nor-2'-脱氧鸟苷的结构类似物（2'NDG），合成并发现抑制1型单纯疱疹病毒（HSV-1）和2型（HSV-2）的复制。随后，由手性中间体制备其旋光异构体（R）-和（S）-iNDG。制备1,2-二-O-苄基-D-和-L-甘油的氯甲基醚，使其与三（三甲基甲硅烷基）鸟嘌呤反应，得到9-烷基化的鸟嘌呤，将其通过催化氢解脱保护。针对细胞培养中的HSV-1和HSV-2，（S）-iNDG的活性比R对映异构体高约10至25倍，并且具有与ACV和2'NDG相当的ED50。（R）-iNDG的活性较差，其磷酸化产物对病毒DNA聚合酶的抑制作用较弱。在小鼠腹膜内或口腔内感染HSV-1或阴道内感染HSV-2的小鼠中，（S）-9-[（2,3-二羟基-1-丙氧基）甲基]鸟嘌呤[（S）-iNDG]的药效低于2

  DOI：

  10.1021/jm00145a014

文献信息

• Anti-viral guanine compounds
  申请人：Merck & Co., Inc.

  公开号：US04816447A1

  公开（公告）日：1989-03-28

  9-(1,3-Dihydroxy-2-propoxymethyl)guanine and 9-(2,3-dihydroxy-1-propoxymethyl)guanine have been found to have potent anti-viral activity against herpes viruses. These compounds, their acyl derivatives, their phosphate derivatives and their pharmaceutically acceptable salts, pharmaceutical formulations containing these compounds, the treatment of DNA viral or herpes viral infections with these compounds, method of preparing these compounds, and novel intermediates useful in their preparation are all disclosed. The compounds may be prepared by reaction of the appropriate acetoxymethyl ether with diacetylguanine, followed by deprotection. The acetoxymethyl ethers may be obtained by reaction of glycerol formal with acetic anhydride in the presence of a catalyst.

  9-(1,3-二羟基-2-丙氧甲基)鸟嘌呤和9-(2,3-二羟基-1-丙氧甲基)鸟嘌呤已被发现对疱疹病毒具有强效的抗病毒活性。本文披露了这些化合物、它们的酰基衍生物、磷酸酯衍生物和药学上可接受的盐、含有这些化合物的制剂、使用这些化合物治疗DNA病毒或疱疹病毒感染的方法、制备这些化合物的方法以及在制备中有用的新中间体。这些化合物可以通过将适当的乙酰氧甲基醚与双乙酰鸟嘌呤反应，然后去保护基来制备。乙酰氧甲基醚可以通过在催化剂存在下将甘油缩醛与乙酸酐反应来获得。
• Process for the preparation of ganciclovir intermediate n2-acetyl-9-(1,3-diacetoxy-2-propoxymethyl) guanine
  申请人：Babu Suresh Jayachandra

  公开号：US20050176956A1

  公开（公告）日：2005-08-11

  The present invention relates to an improved process for the preparation of N 2 -acetyl-9-(1,3-diacetoxy-2-propoxymethyl)guanine, referred to here as the N-9 alkylated isomer, useful as intermediate for the preparation of antiviral compound, ganciclovir, including addition of a monoacetyl guanine, and optionally, addition of N 2 -acetyl-9-(1,3-diacetoxy-2-propoxymethyl)guanine, referred to herein as the N-7 alkylated isomer.

  本发明涉及一种改进的制备N2-乙酰基-9-(1,3-二乙酰氧基-2-丙氧甲基)鸟嘌呤，简称为N-9烷基化异构体的方法，该方法可用作制备抗病毒化合物甘昔洛韦的中间体，包括加入单乙酰基鸟嘌呤，以及可选地加入N2-乙酰基-9-(1,3-二乙酰氧基-2-丙氧甲基)鸟嘌呤，简称为N-7烷基化异构体。
• Anti-viral guanine derivatives
  申请人：Merck & Co., Inc.

  公开号：EP0074306A2

  公开（公告）日：1983-03-16

  9-(1,3-dihydroxy-2-propoxymethyl)guanine and 9-(2,3-dihydroxy-1-propoxymethyl)guanine have been found to have potent anti-viral activity against herpes viruses. These compounds, their acyl derivatives, their phosphate derivatives and their pharmaceutically acceptable salts, pharmaceutical formulations containing these compounds, the treatment of viral infections with these compounds, methods of preparing these compounds, and novel intermediates useful in their preparation are all disclosed. The compounds may be prepared by reaction of the appropriate acetoxymethyl ether with diacetylguanine, followed by deprotection. The acetoxymethyl ethers may be obtained by reaction of glycerol formal with acetic anhydride in the presence of a catalyst.

  已发现 9-(1,3-二羟基-2-丙氧基甲基)鸟嘌呤和 9-(2,3-二羟基-1-丙氧基甲基)鸟嘌呤对疱疹病毒具有很强的抗病毒活性。 现已公开这些化合物、其酰基衍生物、其磷酸盐衍生物及其药学上可接受的盐、含有这些化合物的药物制剂、用这些化合物治疗病毒感染、制备这些化合物的方法以及用于制备这些化合物的新型中间体。 这些化合物可通过适当的乙酰氧甲基醚与二乙酰鸟嘌呤反应，然后进行脱保护来制备。 乙酰氧甲基醚可通过甘油甲醛与乙酸酐在催化剂存在下反应来获得。
• Anti-viral compounds, their preparation and anti-viral compositions
  申请人：Merck & Co., Inc.

  公开号：EP0165164A1

  公开（公告）日：1985-12-18

  9-(1, 3-Dihydroxy-2-propoxymethyl) quanine and 9-(2, 3-dihydroxy-1-propoxymethyl) guanine have been found to have potent anti-viral activity against herpes viruses. These compounds, their acyl derivatieves, their phosphate derivatives and their pharmaceutically acceptable salts, phar-- maceutical formulations containing these compounds, the treatment of DNA viral or herpes viral infections with these compounds, methods of preparing these compounds, and novel intermediates useful in their preparation are all disclosed. The compounds may be prepared by reaction of the appropriate acetoxymethyl ether with diacetyl-quanine, followed by deprotection. The acetoxymethyl ethers may be obtained by reaction of glycerol formal with acetic anhydride in the presence of a catalyst.

  9-(1,3-二羟基-2-丙氧基甲基)鸟嘌呤和9-(2,3-二羟基-1-丙氧基甲基)鸟嘌呤已被发现对疱疹病毒具有很强的抗病毒活性。 本文公开了这些化合物、它们的酰基衍生物、它们的磷酸衍生物和它们的药学上可接受的盐、含有这些化合物的药物制剂、用这些化合物治疗DNA病毒或疱疹病毒感染、制备这些化合物的方法以及用于制备这些化合物的新型中间体。 这些化合物可以通过适当的乙酰氧甲基醚与二乙酰基鸟嘌呤反应，然后进行脱保护来制备。 乙酰氧甲基醚可以通过甘油醛与乙酸酐在催化剂存在下反应来获得。
• Antiviral compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0201289A2

  公开（公告）日：1986-11-12

  Compounds of formula (I) (wherein A represents a or C-NH2 grouping; R1 represents a hydrogen or halogen (e.g. chlorine or bromine) atom or a hydroxy or amino group, R2 represents a hydrogen atom or a C1-4 alkyl (e.g. methyl) group, X represents an oxygen or sulphur group and m and n are 0 or 1 provided that m + n = 1) and physiologically acceptable salts and esters thereof, have been found to have potent antiviral activity particularly against herpes infections.

  式（I）化合物 (其中，A 代表 a 或 C-NH2 基团；R1 代表氢原子或卤素（如氯或溴）原子或羟基或氨基；R2 代表氢原子或 C1-4 烷基（如甲基）；X 代表氧或硫基；m 和 n 为 0 或 1，条件是 m + n = 1）及其生理上可接受的盐和酯，已被发现具有强效抗病毒活性，尤其是针对疱疹病毒感染。