5-amino-1-(β-D-ribofuranosyl)imidazole-4-(N-benzyl)carboxamide | 20735-74-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 5-amino-1-(β-D-ribofuranosyl)imidazole-4-(N-benzyl)carboxamide
• 英文别名: 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxylic acid benzylamide；5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carbonsaeure-benzylamid；5-amino-1-β-D-riboruranosylimidazole-4-N-(benzyl)carboxamide；5-amino-N-benzyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
• CAS: 20735-74-4
• 化学式: C₁₆H₂₀N₄O₅
• 分子量: 348.359
• InChiKey: QEOKLNZVPLJMJR-XNIJJKJLSA-N

物化性质

• 熔点：
  170-173 °C
• 沸点：
  791.7±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  143
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-amino-1-(β-D-ribofuranosyl)imidazole-4-(N-benzyl)carboxamide 在 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：

  N¹-benzylinosine 在 sodium hydroxide 作用下， 以68%的产率得到5-amino-1-(β-D-ribofuranosyl)imidazole-4-(N-benzyl)carboxamide
  参考文献：
  名称：

  从肌苷轻松合成 AICAR

  摘要：

  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。

  DOI：

  10.1055/s-2003-42455

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。
• Conformational restraint is a critical determinant of unnatural nucleotide recognition by protein kinases
  作者：Scott M Ulrich、Nathan A Sallee、Kevan M Shokat

  DOI：10.1016/s0960-894x(02)00616-9

  日期：2002.11

  This report describes the synthesis of N-4-(benzyl) AICAR triphosphate, a conformationally restrained analogue of N-4-(benzyl) ribavirin triphosphate. Both of these nucleotides were evaluated as phosphodonors for wild-type p38 MAP kinase and T106G p38MAP kinase, a designed mutant with expanded nucleotide specificity. The conformationally restrained nucleotide, N-4-(benzyl) AICAR triphosphate, is orthogonal to (not accepted as a substrate by) wild-type p38MAP kinase, in contrast to N-4-(benzyl) ribavirin triphosphate. Furthermore, N-4-(benzyl) AICAR triphosphate, is accepted as a substrate by T106G p38 MAP kinase, in contrast to N-4-(benzyl) ribavirin triphosphate. We hypothesize that the presence of an internal hydrogen bond in N-4-(benzyl) AICAR and its absence in N-4-(benzyl) ribavirin triphosphate is the main determinant for their differing structure-activity relationships. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support
  作者：Giorgia Oliviero、Jussara Amato、Nicola Borbone、Stefano D'Errico、Gennaro Piccialli、Enrico Bucci、Vincenzo Piccialli、Luciano Mayol

  DOI：10.1016/j.tet.2008.04.071

  日期：2008.6

  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.
• WO2006/105167
  申请人：——

  公开号：——

  公开（公告）日：——
• 5-Amino-4-imidazolecarboxamide Riboside from Inosine. Ring-opening Reactions of Purine Nucleosides
  作者：Elliott Shaw

  DOI：10.1021/ja01548a025

  日期：1958.8