N¹-benzylinosine | 31504-19-5

• 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: N¹-benzylinosine
• 英文别名: 1-benzylinosine；1-Benzyl-inosin；N¹-Benzyl-inosin；1-benzyl-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-one
• CAS: 31504-19-5
• 化学式: C₁₇H₁₈N₄O₅
• 分子量: 358.354
• InChiKey: CBMWEMPSBJWKJM-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N¹-benzylinosine 在 sodium hydroxide 、 乙醇 、 氨 、 sodium amide 作用下， 生成 阿卡地新
  参考文献：
  名称：

  5-Amino-4-imidazolecarboxamide Riboside from Inosine. Ring-opening Reactions of Purine Nucleosides

  摘要：

  DOI：

  10.1021/ja01548a025
• 作为产物：
  描述：

  1-(2,4-dinitrophenyl)inosine 、 苄胺 生成 N¹-benzylinosine
  参考文献：
  名称：

  Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support

  摘要：

  Herein, we report the solid-phase synthesis of several 5-aminoimidazole-4-(N-alkyl)carboxamide-1-ribosides (4-N-alkyl AICARs) and the corresponding 2',3'-secoriboside derivatives. The method uses the N-1-dinitrophenyl-inosine 5'-bonded to a solid support. This inosine derivative has the C-2 of the purine base strongly activated towards the attack of N-nucleophiles thus allowing the preparation of several N-1 alkylated inosine supports from which a small library of 4-N-alkyl AICAR derivatives has been synthesized. A set of new 4-N-alkyl AICA-2',3'-secoriboside derivatives have also been obtained in high yields by solid-phase cleavage of the 2',3'-ribose bond. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.071

文献信息

• METHODS, COMPOSITIONS, AND FORMULATIONS FOR PREVENTING OR REDUCING ADVERSE EFFECTS IN A PATIENT
  申请人：Stover Richard R.

  公开号：US20080175891A1

  公开（公告）日：2008-07-24

  The present invention provides transdermal administration of AICA riboside, or a prodrugs, analogs, or salts thereof, and/or a blood clotting inhibitor for preventing or reducing adverse side effects in a patient. The type of patient that may benefit includes a patient with decreased left ventricular function, a patient with a prior myocardial infarction, a patient undergoing non-vascular surgery, or a fetus during labor and delivery.

  本发明提供了通过经皮途径给予AICA核糖苷，或其前药、类似物或盐，和/或血液凝块抑制剂以预防或减少患者的不良副作用。可能受益的患者类型包括左心室功能减退的患者、先前发生心肌梗死的患者、接受非血管手术的患者，或分娩期间的胎儿。
• A Facile Synthesis of AICAR from Inosine
  作者：Yukio Yamamoto、Naoki Kohyama

  DOI：10.1055/s-2003-42455

  日期：——

  5-Amino- 1-β-D-ribofuranosylimidazole-4-carboxamide (AICAR; 1) (Figure I) was efficiently prepared from inosine through its 1-alkoxymethylderivatives. The stability of these derivatives enabled their purification by column chromatography (silica gel). The operation ensured the high quality of 1, which was obtained in good yield through alkaline hydrolysis of the derivatives.

  5-Amino-1-β-D-ribofuranosylimidazole-4-carboxamide (AICAR; 1)（图 I）是由肌苷通过其 1-烷氧基甲基衍生物有效制备的。这些衍生物的稳定性使其能够通过柱色谱法（硅胶）进行纯化。该操作确保了1的高质量，通过衍生物的碱解以良好的收率获得了1。
• Microwave-Assisted Selective 5′-<i>O</i>-Trityl Protection of Inosine Derivatives
  作者：C. Kappe、Elena Casanova、María-Jesús Pérez-Pérez

  DOI：10.1055/s-2007-982532

  日期：2007.7

  The efficient microwave-assisted synthesis of 5′- O-trityl inosine derivatives is described. The reported protocol allows the protection of inosine derivatives in significantly higher yields and shorter reaction times than the standard thermal conditions. This procedure is particularly suitable for modified inosines where the 5′-OH is sterically hindered (i.e. 8-bromoinosine).

  描述了 5'-O-三苯甲基肌苷衍生物的高效微波辅助合成。报告的协议允许以比标准热条件显着更高的产率和更短的反应时间保护肌苷衍生物。该程序特别适用于 5'-OH 位阻的修饰肌苷（即 8-溴肌苷）。
• Synthesis and biological activity of nucleoside analogs involving modifications in the carbohydrate ring
  作者：Walter A. Szarek、B. Mario Pinto、Masaharu Iwakawa

  DOI：10.1139/v85-354

  日期：1985.8.1

  acyclic moiety bearing α,β-unsaturated esters is also illustrated for the case of uridine. The results of biological screening of these analogs and others previously synthesized in our program against leukemia L-1210 cells in vitro are presented; some of these compounds showed marginal antitumor activity. The screening results of selected compounds against the human HeLa cell line in vitro are al...

  描述了涉及碳水化合物环修饰的各种核苷类似物的合成。特别是，已经合成了 1-oxa-4-thiacyclohex 和 1,4-dioxacyclohex 的 6-取代的purin-9-yl 衍生物。许多取代的 1-氧杂-4-硫代环己烷的 6-氯嘌呤-9-基衍生物也已通过普默勒重排从母体化合物中衍生出来。以肌苷为例，说明了从天然核苷获得 1-oxa-4-硫代环己烷核苷类似物的途径。对于尿苷的情况，还说明了获得核苷类似物的途径，其中碳水化合物部分被带有 α,β-不饱和酯的无环部分取代。介绍了这些类似物和其他类似物的生物筛选结果，这些类似物以前在我们的体外抗白血病 L-1210 细胞项目中合成；其中一些化合物显示出微弱的抗肿瘤活性。所选化合物在体外针对人 HeLa 细胞系的筛选结果...
• Synthesis of 2'-"up" fluorinated 2'-deoxy-arabinofuranosyl purines
  申请人：Sloan-Kettering Institute for Cancer Research

  公开号：US05525720A1

  公开（公告）日：1996-06-11

  The present invention provides a compound having the structure: ##STR1## wherein R.sup.1 is hydrogen, benzyl or a substituted benzyl group; X is hydrogen, a flouro, an amino or a substituted amino group; Y is hydrogen, a methoxy, a methylthio, a benzylthio, a methylethyl, a chloro, an amino or a substituted amino group; and Y' is an oxo or a thio group; and Z is hydrogen, a hydroxy, a methoxy, a halogen, an amino or a substituted amino group. The present invention also provides a method of synthesizing a compound having the above-identified structure as well as the intermediate compounds produced according to that method.

  本发明提供了一种具有以下结构的化合物：##STR1##其中R.sup.1是氢，苄基或取代苄基基团；X是氢，氟，氨基或取代氨基基团；Y是氢，甲氧基，甲硫基，苄硫基，甲基乙基，氯，氨基或取代氨基基团；Y'是氧或硫基团；Z是氢，羟基，甲氧基，卤素，氨基或取代氨基基团。本发明还提供了一种合成具有上述结构的化合物的方法，以及根据该方法产生的中间化合物。