8-{[[2-hydroxy-3-[(4-ethoxycarbonyl-2,6-dimethoxy)phenoxy]]propyl]thio}adenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-{[[2-hydroxy-3-[(4-ethoxycarbonyl-2,6-dimethoxy)phenoxy]]propyl]thio}adenosine
• 英文别名: ethyl 4-[3-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-8-yl]sulfanyl-2-hydroxypropoxy]-3,5-dimethoxybenzoate
• 化学式: C₂₄H₃₁N₅O₁₀S
• 分子量: 581.604
• InChiKey: ADTRRQQRVOLPMX-JBBIPTIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  239
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  丁香酸乙酯 在 2,6-二甲基吡啶 、 potassium carbonate 作用下， 以 乙醇 、 丁酮 为溶剂， 生成 8-{[[2-hydroxy-3-[(4-ethoxycarbonyl-2,6-dimethoxy)phenoxy]]propyl]thio}adenosine
  参考文献：
  名称：

  8-Substituted purine derivatives: a new class of lipid-lowering agents

  摘要：

  A series of purine derivatives have been prepared and their in vivo abilities to lower plasma total cholesterol and triglyceride levels, and to elevate high density lipoprotein (HDL) cholesterol levels in hyperlipemic rats have been tested. Some compounds, among which 8-{2-(R)-hydroxy-3-[(p-isobutoxycarbonyl)phenoxy]propylthio}adenosine 31, 8-{3-[(p-isobutoxy carbonyl)phenoxy]-2-oxopropylthio} adenosine 33 and 8-{3-[(p-isobutoxycarbonyl)phenoxy]-2-hydrazonecarboxamidepropylthio} adenosine 36 appear to be the most interesting, have been found to have both the desired profile of activity and no hepatotoxicity, when administered po at 50, 100 or 300 mg/kg. Compounds 31, 33 and 36, orally tested at the same doses in the 15-d test, lower triglyceride and VLDL/LDL (very low density lipoprotein/low density lipoprotein) cholesterol levels by 10-33% and 13-46%, respectively, and increase HDL-associated cholesterol levels by 10-32%. These molecules have been chosen for further pharmacological and toxicological evaluations.

  DOI：

  10.1016/0223-5234(94)90098-1

文献信息

• New 8-substituted nucleoside and purine derivatives, the process for the
  申请人：Pierrel Spa

  公开号：US04774325A1

  公开（公告）日：1988-09-27

  New 8-substituted nucleoside and purine derivatives of the general formula: ##STR1## wherein R represents an amino group or an hydroxy group possibly in the corresponding keto tautomeric form, R.sub.1 is hydrogen or an amino group, R.sub.2 is hydrogen or a .beta.-D-ribofuranosyl radical wherein the primary hydroxy group and/or the two secondary hydroxy groups may be derivatized, R.sub.3 is an optionally substituted aryl or monocyclic heteroaryl radical and, X is --O-- or --S--. The new compounds have antihyperlipaemic activity.

  新的8-取代核苷和嘌呤衍生物的一般公式为：##STR1##其中R代表氨基团或羟基团，可能以相应的酮式互变形式存在，R.sub.1是氢或氨基团，R.sub.2是氢或一个β-D-核糖呋喃基团，其中主要羟基和/或两个次要羟基可以被衍生，R.sub.3是一个可选择取代的芳基或单环杂芳基团，X是--O--或--S--。这些新化合物具有抗高脂血症活性。
• New 8-substituted nucleoside and purine derivatives, the process for the preparation thereof and the pharmaceutical compositions containing them
  申请人：Pierrel S.p.A.

  公开号：EP0175325B1

  公开（公告）日：1989-03-15
• US4774325A
  申请人：——

  公开号：US4774325A

  公开（公告）日：1988-09-27
• 8-Substituted purine derivatives: a new class of lipid-lowering agents
  作者：E Vanotti、M Bani、D Favara、M Gobetti、M Lombroso、S Magnetti、V Olgiati、M Palladino、GC Tonon

  DOI：10.1016/0223-5234(94)90098-1

  日期：1994.1

  A series of purine derivatives have been prepared and their in vivo abilities to lower plasma total cholesterol and triglyceride levels, and to elevate high density lipoprotein (HDL) cholesterol levels in hyperlipemic rats have been tested. Some compounds, among which 8-2-(R)-hydroxy-3-[(p-isobutoxycarbonyl)phenoxy]propylthio}adenosine 31, 8-3-[(p-isobutoxy carbonyl)phenoxy]-2-oxopropylthio} adenosine 33 and 8-3-[(p-isobutoxycarbonyl)phenoxy]-2-hydrazonecarboxamidepropylthio} adenosine 36 appear to be the most interesting, have been found to have both the desired profile of activity and no hepatotoxicity, when administered po at 50, 100 or 300 mg/kg. Compounds 31, 33 and 36, orally tested at the same doses in the 15-d test, lower triglyceride and VLDL/LDL (very low density lipoprotein/low density lipoprotein) cholesterol levels by 10-33% and 13-46%, respectively, and increase HDL-associated cholesterol levels by 10-32%. These molecules have been chosen for further pharmacological and toxicological evaluations.