[5-(6-氨基嘌呤-9-基)呋喃-2-基]甲醇 | 61130-78-7

• 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
• 中文名称: [5-(6-氨基嘌呤-9-基)呋喃-2-基]甲醇
• 英文名称: [5-(6-amino-9H-purin-9-yl)-2-furyl]methanol
• 英文别名: [5-(6-amino-purin-9-yl)-furan-2-yl]-methanol；9-(5-Hydroxymethylfuran-2-yl)adenin；[5-(6-Amino-9H-purin-9-yl)furan-2-yl]methanol；[5-(6-aminopurin-9-yl)furan-2-yl]methanol
• CAS: 61130-78-7
• 化学式: C₁₀H₉N₅O₂
• 分子量: 231.214
• InChiKey: PCVSGOKFMHYKSA-UHFFFAOYSA-N

物化性质

• 沸点：
  557.1±60.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)腺苷 在 吡啶 、 咪唑 、 1,5-二氮杂双环[4.3.0]壬-5-烯 、 碘 、 溶剂黄146 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 甲苯 为溶剂， 反应 28.0h， 生成 [5-(6-氨基嘌呤-9-基)呋喃-2-基]甲醇
  参考文献：
  名称：

  Synthesis of {[5-(adenin-9-yl)-2-furyl]methoxy}methyl phosphonic acid and evaluations against human adenylate kinases

  摘要：

  AMP mimics constitute an important class of therapeutic derivatives to treat diseases where the pool of ATP is involved. A new phosphonate derivative of 9-(5-hydroxymethylfuran-2-yl)adenine was synthesized in a multi-step sequence from commercially available adenosine. Its ability to behave as a substrate of human adenylate kinases 1 and 2 was assessed. The phosphonate was shown to be a moderate but selective substrate of the mitochondrial human AK2, better than well-known antiviral acyclic phosphonates 9-(2-phosphonomethoxyethyl)adenine (PMEA, Adefovir) and (R)-9-(2-phosphonomethoxypropyl)adenine (PMPA, Tenofovir). Putative binding mode within adenylate kinase NMP site revealed by molecular docking in comparison to AMP native substrate allowed to illustrate this selective behavior.

  DOI：

  10.1016/j.bmcl.2014.07.036

文献信息

• Direct strand cleavage via furanyladenine formation in anaerobic photoirradiation of 5-bromouracil-containing oligonucleotides
  作者：Kenzo Fujimoto、Yutaka Ikeda、Isao Saito

  DOI：10.1016/s0040-4039(00)01026-1

  日期：2000.8

  The mechanism of direct strand cleavage induced by anaerobic irradiation of 5-bromouracil (U-Br)- containing DNA was investigated. The formation of an oligonucleotide fragment containing 3'-furanyladenine end like 5 was observed as a major photoproduct for the direct strand breaks. (C) 2000 Elsevier Science Ltd. All rights reserved.