9-<(1,3-dipivaloyloxy-2-propoxy)methyl>guanine

• 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: 9-<(1,3-dipivaloyloxy-2-propoxy)methyl>guanine
• 英文别名: 9-(1,3-Di-(2,2-dimethylpropanoyloxy)-2-propoxymethyl)guanine；[2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]-3-(2,2-dimethylpropanoyloxy)propyl] 2,2-dimethylpropanoate
• 化学式: C₁₉H₂₉N₅O₆
• 分子量: 423.469
• InChiKey: PJWVIYVXUNFHQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  更昔洛韦 生成 9-<(1,3-dipivaloyloxy-2-propoxy)methyl>guanine
  参考文献：
  名称：

  VERHEYDEN, JULIEN P. H.;MARTIN, JOHN C.

  摘要：

  DOI：

文献信息

• Synthesis and Antiviral Activity of Various Esters of 9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine
  作者：John C. Martin、Michael A. Tippie、Danny P.C. McGee、Julien P.H. Verheyden

  DOI：10.1002/jps.2600760221

  日期：1987.2

  The synthesis and in vivo biological activity of a series of mono-O-, di-O-, and N2-acyl derivatives of 9-[(1,3-dihydro-2-propoxy)-methyl]guanine (DHPG) are described.

  描述了9-[（1,3-二氢-2-丙氧基）-甲基]鸟嘌呤（DHPG）的一系列单-O-，二-O-和N2-酰基衍生物的合成和体内生物学活性。
• Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl)
  申请人：Syntex Inc.

  公开号：US05250535A1

  公开（公告）日：1993-10-05

  Compounds useful as antiviral agents are defined by the following formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof wherein R.sup.1 is hydrogen or --C(O)R.sup.7 wherein R.sup.7 is hydrogen, alkyl of one to nineteen carbon atoms, hydroxyalkyl of one to eight carbon atoms, alkoxyalkyl of two to nine carbon atoms, alkenyl of two to nineteen carbon atoms, phenyl, 1-adamantyl or 2-carboxyethyl and the pharmaceutically acceptable alkali metal salts thereof; R.sup.2 is --C(O)R.sup.7 wherein R.sup.7 is as defined above; R.sup.3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR.sup.9 R.sup.10 wherein R.sup.9 and R.sup.10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R.sup.8 wherein R.sup.8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R.sup.6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR.sup.9 R.sup.10 wherein R.sup.9 and R.sup.10 are as defined above or --NHC(O)R.sup.8 wherein R.sup.8 is as defined above and R.sup.4 together with R.sup.5 is a bond; or (b) R.sup.5 together with R.sup.6 is a keto group and R.sup.4 is hydrogen.

  具有抗病毒作用的化合物的定义如下式所示：##STR1##和其药学上可接受的酸盐，其中R.sup.1是氢或--C(O)R.sup.7，其中R.sup.7是氢，一至十九个碳原子的烷基，一至八个碳原子的羟基烷基，二至九个碳原子的烷氧基烷基，二至十九个碳原子的烯基，苯基，1-金刚烷基或2-羧乙基及其药学上可接受的碱金属盐；R.sup.2是--C(O)R.sup.7，其中R.sup.7如上所定义；R.sup.3是氢，卤素，硫，一至六个碳原子的低烷基硫，叠氮，NR.sup.9 R.sup.10，其中R.sup.9和R.sup.10独立地是氢或一至六个碳原子的低烷基或--NHC(O)R.sup.8，其中R.sup.8是氢，一至十九个碳原子的烷基或1-金刚烷基；以及(a) R.sup.6是氢，卤素，一至六个碳原子的低烷氧基，叠氮，硫，一至六个碳原子的低烷基硫，--NR.sup.9 R.sup.10，其中R.sup.9和R.sup.10如上所定义，或--NHC(O)R.sup.8，其中R.sup.8如上所定义，而R.sup.4与R.sup.5一起是一个键；或(b) R.sup.5与R.sup.6一起是一个酮基，而R.sup.4是氢。
• Process for preparing guanine derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04803271A1

  公开（公告）日：1989-02-07

  Compounds useful as antiviral agents are defined by the following formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof wherein R.sup.1 is hydrogen or --C(O)R.sup.7 wherein R.sup.7 is hydrogen, alkyl of one to nineteen carbon atoms, hydroxyalkyl of one to eight carbon atoms, alkoxyalkyl of two to nine carbon atoms, alkenyl of two to nineteen carbon atoms, phenyl, 1-adamantyl or 2-carboxyethyl and the pharmaceutically acceptable alkali metal salts thereof; R.sup.2 is --C(O)R.sup.7 is as defined above; R.sup.3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR.sup.9 R.sup.10 wherein R.sup.9 and R.sup.10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R.sup.8 wherein R.sup.8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R.sup.6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR.sup.9 R.sup.10 and R.sup.9 and R.sup.10 are as defined above or --NHC(O)R.sup.8 is as defined above and R.sup.4 together with R.sup.5 is a bond; or (b) R.sup.5 together with R.sup.6 is a keto group and R.sup.4 is hydrogen.

  具有抗病毒活性的化合物的定义式为：##STR1##及其药学上可接受的酸盐，其中R.sup.1为氢或--C（O）R.sup.7，其中R.sup.7为氢、1至19个碳原子的烷基、1至8个碳原子的羟基烷基、2至9个碳原子的烷氧基烷基、2至19个碳原子的烯基、苯基、1-金刚烷基或2-羧乙基及其药学上可接受的碱金属盐；R.sup.2为--C（O）R.sup.7，如上所定义；R.sup.3为氢、卤素、硫、1至6个碳原子的低烷基硫、偶氮基、NR.sup.9 R.sup.10，其中R.sup.9和R.sup.10独立地为氢或1至6个碳原子的低烷基，或--NHC（O）R.sup.8，其中R.sup.8为氢、1至19个碳原子的烷基或1-金刚烷基；以及（a）R.sup.6为氢、卤素、1至6个碳原子的低烷氧基、偶氮基、硫、1至6个碳原子的低烷基硫、--NR.sup.9 R.sup.10，其中R.sup.9和R.sup.10如上所定义，或--NHC（O）R.sup.8如上所定义，且R.sup.4与R.sup.5一起为键；或（b）R.sup.5与R.sup.6一起为酮基，R.sup.4为氢。
• Process for preparing
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04621140A1

  公开（公告）日：1986-11-04

  Process and novel intermediates for preparing 9-(1,3-dihydroxy-2-propoxymethyl)guanine and 2,6-diamino-9-(1,3-dihydroxy-2-propoxymethyl)purine and certain esters thereof. The present process and intermediates reduce the number of reaction steps to prepare these compounds as compared to prior processes. The products are useful as antiviral agents.

  制备9-(1,3-二羟基-2-丙氧甲基)鸟嘌呤、2,6-二氨基-9-(1,3-二羟基-2-丙氧甲基)嘌呤及其某些酯类的新型中间体和工艺。与之前的工艺相比，本工艺和中间体减少了制备这些化合物的反应步骤。这些产品可用作抗病毒剂。
• Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl)purines as antiviral agent
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0085424A2

  公开（公告）日：1983-08-10

  Compounds useful as antiviral agents are defined by the following formula: and the acid addition salts, preferably the pharmaceutically acceptable acid addition salt thereof, wherein R1 is hydrogen or -C(O)R7 wherein R7 is hydrogen, alkyl of one to nineteen carbon atoms, hydroxyalkyl of one to eight carbon atoms, alkoxyalkyl of two to nine carbon atoms, alkenyl of two to nineteen carbon atoms, phenyl, 1- adamantyl, 2-carboxyethyl or carboxymethyl and the pharmaceutically acceptable alkali metal salts thereof; R2 is -C(O)R7 wherein R7 is as defined above; R3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR9R10 wherein R9 and R10 are independently hydrogen or lower alkyl of one to six carbon atoms or -NHC(O)R8 wherein R8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkythio of one to six carbon atoms, -NR9R10 wherein R9 and R10 are as defined above or -NHC(O)R8 wherein R8 is as defined above and R4 together with R5 is a single bond; or (b) R5 together with R6 is a keto group and R4 is hydrogen.

  可用作抗病毒剂的化合物由下式定义： 及其酸加成盐，最好是药学上可接受的酸加成盐，其中 R1 是氢或-C(O)R7，其中 R7 是氢、1 至 19 个碳原子的烷基、1 至 8 个碳原子的羟烷基、2 至 9 个碳原子的烷氧基烷基、2 至 19 个碳原子的烯基、苯基、1-金刚烷基、2-羧乙基或羧甲基及其药学上可接受的碱金属盐； R2 是-C(O)R7，其中 R7 如上定义； R3 是氢、卤代、硫代、一至六个碳原子的低级烷硫基、叠氮、NR9R10（其中 R9 和 R10 独立地是氢或一至六个碳原子的低级烷基）或-NHC(O)R8（其中 R8 是氢、一至十九个碳原子的烷基或 1-金刚烷基）；以及 (a) R6 为氢、卤素、一至六个碳原子的低级烷氧基、叠氮、硫代、一至六个碳原子的低级烷硫基、-NR9R10（其中 R9 和 R10 如上所定义）或-NHC(O)R8（其中 R8 如上所定义），且 R4 与 R5 一起为单键；或 (b) R5 与 R6 同为酮基，R4 为氢。