9-(morpholin-4'-yl)methyl-S⁶-acetyloxymethyl-6-mercaptopurine | 132228-74-1

• 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: 9-(morpholin-4'-yl)methyl-S⁶-acetyloxymethyl-6-mercaptopurine
• 英文别名: NSC647471；((9-(4-Morpholinylmethyl)-9H-purin-6-yl)thio)methyl acetate；[9-(morpholin-4-ylmethyl)purin-6-yl]sulfanylmethyl acetate
• CAS: 132228-74-1
• 化学式: C₁₃H₁₇N₅O₃S
• 分子量: 323.376
• InChiKey: JFRCSXJCJMYMNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  吗啉 、 聚合甲醛 、 S6-乙酰氧基甲基-6-巯基嘌呤 在 三乙胺 作用下， 生成 9-(morpholin-4'-yl)methyl-S⁶-acetyloxymethyl-6-mercaptopurine
  参考文献：
  名称：

  氨基甲基（N-曼尼希碱）衍生化对S6-乙酰氧基甲基-6-巯基嘌呤前药通过无毛小鼠皮肤递送6-巯基嘌呤的能力的影响。

  摘要：

  合成并表征了一系列9-氨基甲基-S6-乙酰氧基甲基-6-巯嘌呤（9-AM-6-AOM-6-MP）前药，它们通过无毛递送总6-巯基嘌呤（6-MP）的能力小鼠皮肤已被测量。9-AM-6-AOM-6-MP前药在肉豆蔻酸异丙酯（IPM）中的溶解度比S6-乙酰氧基甲基-6-MP（6-AOM-6-MP）本身或相应的7-氨基甲基-6- MP（7-AM-6-MP）前药。9-AM-6-AOM-6-MP前药在递送总6-MP方面比6-AOM-6-MP都更有效（1.8-4倍），但哌啶基甲基衍生物的药效相当。交货。9-AM-6-AOM-6-MP前药在递送6-MP方面也比相应的7-AM-6-MP前药更有效（7-27倍），除了二乙氨基甲基衍生物仅能提供可比的交货率。与9-氨基甲基-S6-新戊酰氧基甲基-6-MP（9-AM-6-POM-6-MP）衍生物形成对比的是，后者通常会递送或多或少完整的S6-新戊酰氧基甲基-6-MP（6-POM-6

  DOI：

  10.1002/jps.2600791212

文献信息

• SAAB, AKRAM N.;SLOAN, KENNETH B.;BEALL, HOWARD D.;VILLANUEVA, RENE, J. PHARM. SCI., 79,(1991) N2, C. 1099-1104
  作者：SAAB, AKRAM N.、SLOAN, KENNETH B.、BEALL, HOWARD D.、VILLANUEVA, RENE

  DOI：——

  日期：——
• 6-ETHER/THIOETHER-PURINES AS TOPOISOMERASE II CATALYTIC INHIBITORS AND THEIR USE IN THERAPY
  申请人：Jensen Lars Hollund

  公开号：US20090209535A1

  公开（公告）日：2009-08-20

  The present invention relates to certain purines of the following formulae, which act as topoisomerase II catalytic inhibitors: wherein: J is independently: —H or —NR N1 R N2 ; X is independently: —O—, or —S—; Q is independently: a covalent bond, C 1-7 alkylene, C 2-7 alkenylene, C 2-7 alkynylene, C 3-7 cycloalkylene, C 3-7 cycloalkenylene, or C 3-7 cycloalkynylene; T is independently: a group A 1 or a group A 2 ; A 1 is independently: C 6-14 carboaryl, C 5-14 heteroaryl, C 3-12 carbocyclic, or C 3-12 heterocyclic; and is independently unsubstituted or substituted; A 2 is independently: —H, —CN, —OH, or —O(C═O)—C 1-7 alkyl; R N is independently —H or a nitrogen ring substituent; R 8 is independently —H or a ring substituent; either: each of R N1 and R N2 is independently —H or a nitrogen substituent; or: R N1 and R N2 taken together with the nitrogen atom to which they are attached form a ring having from 3 to 7 ring atoms; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, N-oxides, chemically protected forms, and prodrugs thereof. These compounds are useful in combination with topoisomerase II poisons, such as anthracyclines and epipodophyllotoxins, in the treatment of proliferative conditions (e.g., cancer). These compounds are also useful in the treatment of tissue damage associated with extravasation of a topoisomerase II poison, such as an anthracycline or an epipodophyllotoxin.
• Effect of Aminomethyl (N-Mannich Base) Derivatization on the Ability of S6Acetyloxymethyl-S-Mercaptopurine Prodrug to Deliver 6-Mercaptopurine through Hairless Mouse Skin
  作者：Akram N. Saab、Kenneth B. Sloan、Howard D. Beall、René Villanueva

  DOI：10.1002/jps.2600791212

  日期：1990.12

  (9-AM-6-AOM-6-MP) prodrugs have been synthesized and characterized, and their ability to deliver total 6-mercaptopurine (6-MP) through hairless mouse skin has been measured. The 9-AM-6-AOM-6-MP prodrugs are much more soluble in isopropyl myristate (IPM) than S6-acetyloxymethyl-6-MP (6-AOM-6-MP) itself or the corresponding 7-aminomethyl-6-MP (7-AM-6-MP) prodrugs. The 9-AM-6-AOM-6-MP prodrugs were all more

  合成并表征了一系列9-氨基甲基-S6-乙酰氧基甲基-6-巯嘌呤（9-AM-6-AOM-6-MP）前药，它们通过无毛递送总6-巯基嘌呤（6-MP）的能力小鼠皮肤已被测量。9-AM-6-AOM-6-MP前药在肉豆蔻酸异丙酯（IPM）中的溶解度比S6-乙酰氧基甲基-6-MP（6-AOM-6-MP）本身或相应的7-氨基甲基-6- MP（7-AM-6-MP）前药。9-AM-6-AOM-6-MP前药在递送总6-MP方面比6-AOM-6-MP都更有效（1.8-4倍），但哌啶基甲基衍生物的药效相当。交货。9-AM-6-AOM-6-MP前药在递送6-MP方面也比相应的7-AM-6-MP前药更有效（7-27倍），除了二乙氨基甲基衍生物仅能提供可比的交货率。与9-氨基甲基-S6-新戊酰氧基甲基-6-MP（9-AM-6-POM-6-MP）衍生物形成对比的是，后者通常会递送或多或少完整的S6-新戊酰氧基甲基-6-MP（6-POM-6