2-Nitrosoadenosine | 383364-90-7

• 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: 2-Nitrosoadenosine
• 英文别名: (2R,3R,4S,5R)-2-(6-amino-2-nitrosopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 383364-90-7
• 化学式: C₁₀H₁₂N₆O₅
• 分子量: 296.242
• InChiKey: RIAJKIRSFJZWEJ-UUOKFMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-Nitrosoadenosine 、 phenyl hydrazinecarboxylate 在 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 以32%的产率得到2-(3-phenyloxycarbonyltriazene-1-yl)adenosine
  参考文献：
  名称：

  N⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor

  摘要：

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.

  DOI：

  10.1021/jm021074j
• 作为产物：
  描述：

  2′,3′,5′-tri-O-acetyl-2-nitrosoadenosine 在 potassium cyanide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.75h， 生成 2-Nitrosoadenosine
  参考文献：
  名称：

  Synthesis and properties of 2-nitrosoadenosine

  摘要：

  一系列新的2取代腺苷衍生物是通过与2-亚硝基腺苷三乙酸酯4进行加成和缩合反应合成的。腺苷亚硝基功能团的优异反应性通过与烯烃（4 + 2环加成反应）、环己烯（“烯”反应）、呋喃（加成/重排反应）和苯胺（米尔斯偶联）等反应得到了证明。2-亚硝基腺苷三乙酸酯是通过对6-氯嘌呤核苷三乙酸酯进行2位的硝化反应，然后再对硝基进行还原/氧化反应合成的。4的脆弱亚硝基功能团需要通过与环戊二烯进行4 + 2环加成反应进行保护，以使RNA环的去酰化成为可能。在95°C下，去酰化产物的反向Diels-Alder反应生成了标题化合物2-亚硝基腺苷7。通过改变温度、浓度和溶剂，研究了三乙酸酯4的亚硝基功能团的二聚化过程。特别是，温度的变化对这种二聚化反应起到了控制作用：在65°C时为100%单体，在-20°C时则完全二聚化。

  DOI：

  10.1039/b102897a

文献信息

• 2-Substituted-1-deaza purine derivatives with adenosine receptor modulating activity
  申请人：Koch Melle

  公开号：US20060052412A1

  公开（公告）日：2006-03-09

  The present invention relates to 2-substituted-1-deaza purine derivatives as adenosine receptor modulating agents, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said purine derivatives. The compounds have the general formula (1) wherein the symbols have the meanings given in the specification.

  本发明涉及2-取代-1-去氮嘌呤衍生物作为腺苷受体调节剂，以及制备这些化合物的方法和用于合成所述嘌呤衍生物的新型中间体。这些化合物具有通式（1），其中符号具有规范中所给出的含义。
• Organic Compounds
  申请人：Fairhurst Robin Alec

  公开号：US20090240045A1

  公开（公告）日：2009-09-24

  A compound of formula (I) or stereoisomers or pharmaceutically acceptable salts thereof, and their preparation and use as pharmaceuticals wherein R 1 , R 2 , R 3 , R 4 and W are as defined herein.

  式(I)的化合物，或其立体异构体或药学上可接受的盐，以及它们的制备和用作药物，其中R1、R2、R3、R4和W的定义如本文所述。
• 2-SUBSTITUTED-1-DEAZA PURINE DERIVATIVES WITH ADENOSINE RECEPTOR MODULATING ACTIVITY
  申请人：Solvay Pharmaceuticals B.V.

  公开号：EP1791841A1

  公开（公告）日：2007-06-06
• ADENOSINE DERIVATIVES HAVING A2A RECEPTOR ACTIVITY
  申请人：Novartis AG

  公开号：EP1861412A1

  公开（公告）日：2007-12-05
• USE OF 2-(PURIN-9-YL)-TETRAHYDOFURAN-3,4-DIOL DERIVATIVES AS ADENOSINE A2A RECEPTOR AGONISTS
  申请人：NOVARTIS AG

  公开号：EP2018381A2

  公开（公告）日：2009-01-28