5'-amino-5'-deoxy-5'-noraristeromycin

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5'-amino-5'-deoxy-5'-noraristeromycin
• 英文别名: (1S,2R,3S,5R)-3-amino-5-(6-amino-9H-purin-9-yl)cyclopentane-1,2-diol；(1S,2R,3S,5R)-3-amino-5-(6-aminopurin-9-yl)cyclopentane-1,2-diol
• 化学式: C₁₀H₁₄N₆O₂
• 分子量: 250.26
• InChiKey: WOKQQQHPTQJHRF-LAHCRNKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1R,4S)-4-azido-1-(6-amino-9H-purin-9-yl)cyclopent-2-ene 在 palladium on activated charcoal 、 四氧化锇 氢气 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 53.0h， 生成 5'-amino-5'-deoxy-5'-noraristeromycin
  参考文献：
  名称：

  5'-氨基-5'-脱氧-5'-诺拉霉素。

  摘要：

  DOI：

  10.1021/jo972078c

文献信息

• Synthesis of 4′-modified noraristeromycins to clarify the effect of the 4′-hydroxyl groups for inhibitory activity against S-adenosyl-l-homocysteine hydrolase
  作者：Takayuki Ando、Kenji Kojima、Praveen Chahota、Atsushi Kozaki、Nikalje D. Milind、Yukio Kitade

  DOI：10.1016/j.bmcl.2008.03.029

  日期：2008.4

  4'-Modified noraristeromycin (NAM) analogs, 4'-sulfo-, 4'-sulfamoy, 4'-azido and 4'-amino-NAM, were systematically synthesized. The inhibitory activities of these analogs and related compounds against Plasmodium falciparum and human S-adenosyl-L-homocysteine hydrolase were investigated. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Novel Carbocyclic Adenosine Analogues as Inhibitors of Adenosine Kinase
  作者：Marlon Cowart、Michael J. Bennett、James F. Kerwin

  DOI：10.1021/jo981658m

  日期：1999.4.1

  Several new 4'-amino substituted carbocyclic adenosine analogues (6, 7, 31) were prepared as potential inhibitors of the enzyme adenosine kinase. Three different heterocyclic base moieties (adenine, 8-azaadenine, and pyrazolo[3,4-d]pyrimidine) were incorporated into carbocyclic nucleoside analogues through the use of two different synthetic strategies. In both strategies, bicyclic isoxazolidine 9 (prepared through a hetero Diels-Alder reaction with cyclopentadiene) was used as the starting material. In one route, the N-O bond was reductively cleaved, and the hydroxyl group (after inversion and ring functionalization) was used as a leaving group to incorporate the heterocyclic base moiety as the key bond-forming step. A second, more efficient and higher yielding synthetic route was developed as a general solution to the synthesis of the target 4'-amino substituted carbocyclic adenosine analogues. In this methodology, the allylic C-O bond in the bicyclic isoxazolidine 9 was cleaved with double stereoinversion under palladium(0) catalysis as the key bond-forming step to stereospecifically incorporate the heterocyclic base moiety into the cyclopentane ring. The regioselectivity of key bond-forming steps was established principally by NMR methods, especially through (13)C NMR shifts and by NOE effects seen in the analogues, as well as by HMBC/HMQC experiments.
• BETA-CELL REPLICATION PROMOTING COMPOUNDS AND METHODS OF THEIR USE
  申请人：Annes Justin P.

  公开号：US20130023491A1

  公开（公告）日：2013-01-24

  In the invention provides for a method of stimulating or increasing β-cell replication or growth, by contacting a β-cell with an inhibitor of adenosine kinase (ADK), an inhibitor of S-Adenosylhomocysteine hydrolase (SAHH) or an activator of AMP activated protein kinase (AMPK).
• 5‘-Amino-5‘-deoxy-5‘-noraristeromycin
  作者：Vishnumurthy R. Hegde、Katherine L. Seley、Stewart W. Schneller、Thomas J. J. Elder

  DOI：10.1021/jo972078c

  日期：1998.10.1