(Z)-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one oxime | 7269-58-1

• 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: (Z)-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one oxime
• 英文别名: 2-amino-N⁶-hydroxyadenosine
• CAS: 7269-58-1
• 化学式: C₁₀H₁₄N₆O₅
• 分子量: 298.26
• InChiKey: TUQQCMYCSWRQCO-UUOKFMHZSA-N

物化性质

• 熔点：
  232 °C
• 沸点：
  833.4±75.0 °C(Predicted)
• 密度：
  2.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  6-氯鸟嘌呤核苷 在 羟胺 作用下， 以 乙醇 、 水 为溶剂， 以69%的产率得到(Z)-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one oxime
  参考文献：
  名称：

  Anti-malarial activity of N6-modified purine analogues

  摘要：

  Plasmodium falciparum causes one of the deadliest forms of malaria and resistance to the currently available drugs makes it imperative to develop new, safe and potent drugs. Parasites such as P. falciparum are unable to synthesise purines de novo and to this end often have multiple purine uptake and salvage systems. With this in mind, we have designed and synthesised libraries of purine analogues as potential anti-malarial agents. Herein, we report three compounds with promising activity against the highly chloroquine-resistant VS1 P. falciparum namely: N-6-hydroxyadenine (1c), 2-amino-N-6-aminoadenosine (2b) and 2-amino-N-6-amino-N-6-methyladenosine (4b). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.038

文献信息

• Evidence for the Existence of a Specific G Protein-Coupled Receptor Activated by Guanosine
  作者：Rosaria Volpini、Gabriella Marucci、Michela Buccioni、Diego Dal Ben、Catia Lambertucci、Carmen Lammi、Ram C. Mishra、Ajiroghene Thomas、Gloria Cristalli

  DOI：10.1002/cmdc.201100100

  日期：2011.6.6

  Guanosine, released extracellularly from neurons and glial cells, plays important roles in the central nervous system, including neuroprotection. The innovative DELFIA Eu‐GTP binding assay was optimized for characterization of the putative guanosine receptor binding site at rat brain membranes by using a series of novel and known guanosine derivatives. These nucleosides were prepared by modifying the

  从神经元和神经胶质细胞向细胞外释放的鸟苷在中枢神经系统中起着重要作用，包括神经保护作用。创新的DELFIA Eu-GTP结合测定法通过使用一系列新颖和已知的鸟苷衍生物来优化在大鼠脑膜上假定的鸟苷受体结合位点的表征。这些核苷分别通过修饰鸟苷的6和5'位置的嘌呤和糖部分来制备。这些实验的结果证明，鸟苷，6-硫代鸟苷及其衍生物激活了一个G蛋白偶联受体，该受体不同于特征明确的腺苷受体。
• Inhibition of viruses
  申请人：Loakes David

  公开号：US20050043268A1

  公开（公告）日：2005-02-24

  Disclosed is a pharmaceutical composition comprising a ribonucleoside analogue in accordance with general formula (I) or (II) as herein defined in admixture with a physiologically acceptable excipient diluent or carrier.

  本发明公开了一种药物组合物，该组合物包含符合本文定义的通式（I）或（II）的核糖核苷类似物，并与生理学上可接受的赋形剂稀释剂或载体混合。
• NOVEL ADENOSINE DERIVATIVES
  申请人：NOVO NORDISK A/S

  公开号：EP0607367A1

  公开（公告）日：1994-07-27
• US5430027A
  申请人：——

  公开号：US5430027A

  公开（公告）日：1995-07-04
• US5589467A
  申请人：——

  公开号：US5589467A

  公开（公告）日：1996-12-31