5-氨基腺苷酸 | 14365-44-7

• 物质功能分类: 生物化工 - 核苷类药物 - 脱氧核苷酸及其类似物
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 中文名称: 5-氨基腺苷酸
• 英文名称: 5'-amino-5'-deoxyadenosine
• 英文别名: 5'-Deoxy-5'-aminoadenosine；5'-aminoadenosine；(2R,3S,4R,5R)-2-(aminomethyl)-5-(6-aminopurin-9-yl)oxolane-3,4-diol
• CAS: 14365-44-7
• 化学式: C₁₀H₁₄N₆O₃
• 分子量: 266.26
• InChiKey: GVSGUDGNTHCZHI-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 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：
  145
• 氢给体数：
  4
• 氢受体数：
  8

制备方法与用途

5'-氨基-5'-脱氧腺苷（NH2dAdo；Nsc 238990）是一种嘌呤核苷类似物，具有广泛的抗肿瘤活性，主要针对惰性淋巴系统恶性肿瘤。其抗癌机制依赖于抑制DNA合成和诱导细胞凋亡等过程。

反应信息

• 作为反应物：
  描述：

  5-氨基腺苷酸 在 盐酸 、 adenosine-desaminase 作用下， 以 水 为溶剂， 以93%的产率得到5'-Amino-5'-desoxyinosin
  参考文献：
  名称：

  Morr, Michael; Heeg, Erich, Liebigs Annalen der Chemie, 1983, # 4, p. 575 - 584

  摘要：

  DOI：
• 作为产物：
  描述：

  N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-methylsulfonyladenosine 在 Lindlar's catalyst sodium azide 、 氢气 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.25h， 生成 5-氨基腺苷酸
  参考文献：
  名称：

  Design, synthesis, and molecular modeling studies of 5′-deoxy-5′-ureidoadenosine: 5′-ureido group as multiple hydrogen bonding donor in the active site of S-adenosylhomocysteine hydrolase

  摘要：

  5'-Deoxy-5'-ureidoadenosine was designed and synthesized as a potent inhibitor of S-adenosylhomocysteine hydrolase (SAH), in which 5'-ureido group acted as multiple hydrogen bonding donor in binding with active site residues of SAH in the molecular modeling study. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.06.013

文献信息

• Bridged isocytosine-adenosine compounds: Synthesis and antibacterial evaluation
  作者：O. William Lever、B. Randall Vestal

  DOI：10.1002/jhet.5570230348

  日期：1986.5

  In an approach to novel antibacterial agents, we synthesized a series of 5-nitrosoisocytosines in which a 6-alkylamino substituent is bridged, through an amide linkage at the terminus of the alkyl chain, to the 5′-position of a 5′-deoxyadenosine moiety. A corresponding series of 5-nitro analogues were also prepared. None of the bridged compounds showed significant antibacterial activity.

  在一种新型抗菌剂的方法中，我们合成了一系列5-亚硝基异胞嘧啶，其中6-烷基氨基取代基通过烷基链末端的酰胺键桥接至5'-脱氧腺苷的5'-位部分。还制备了相应的5-硝基类似物系列。没有一种桥接化合物显示出明显的抗菌活性。
• The aqueous N-phosphorylation and N-thiophosphorylation of aminonucleosides
  作者：Louis P. Conway、Richard J. Delley、Jonathan Neville、Gemma R. Freeman、Hannah J. Maple、Vincent Chan、Alexander J. Hall、David R. W. Hodgson

  DOI：10.1039/c4ra08317b

  日期：——

  We demonstrate N-phosphorylation and N-thiophosphorylation of unprotected aminonucleosides in aqueous media. N-Phosphorylations using phosphoric chloride and N-thiophosphorylations using thiophosphoryl chloride were explored as functions of pH using 5′-amino-5′-deoxyguanosine as substrate. These reagents were compared to phosphodichloridate and thiophosphodichloridate ions, and the methodology was applied to other aminonucleosides. S-Alkylations of the nucleoside N-thiophosphoramidates were investigated as functions of pH and alkylating agent.

  我们在水介质中证明了无保护氨基核苷的N-磷酸化和N-硫磷酸化。以5'-氨基-5'-脱氧鸟苷为底物，探索了使用磷酰氯进行N-磷酸化和使用硫磷酰氯进行N-硫磷酸化作为pH值的函数。将这些试剂与磷二氯酸酯和硫磷二氯酸酯离子进行了比较，并将该方法应用于其他氨基核苷。以pH值和烷基化剂为函数，研究了核苷N-硫磷酰胺的S-烷基化。
• Bisubstrate inhibitors for the enzyme catechol-O-methyltransferase (COMT): influence of inhibitor preorganisation and linker length between the two substrate moieties on binding affinity
  作者：Christian Lerner、Birgit Masjost、Armin Ruf、Volker Gramlich、Roland Jakob-Roetne、Gerhard Zürcher、Edilio Borroni、François Diederich

  DOI：10.1039/b208690p

  日期：——

  Inhibition of the enzyme catechol-O-methyltransferase (COMT) is an important approach in the treatment of Parkinson's disease. A series of new potent bisubstrate inhibitors for COMT, resulting from X-ray structure-based design and featuring adenosine and catechol moieties have been synthesised. Biological results show a large dependence of binding affinity on inhibitor preorganisation and the length of the linker between nucleoside and catechol moieties. The most potent bisubstrate inhibitor for COMT has an IC50 value of 9 nM. It exhibits competitive kinetics for the SAM and mixed inhibition kinetics for the catechol binding site. Its bisubstrate binding mode was confirmed by X-ray structure analysis of the ternary complex formed by the inhibitor, COMT and a Mg2+ ion.

  抑制儿茶酚-O-甲基转移酶(COMT)是治疗帕金森病的重要方法。根据基于X射线结构设计的原理，一系列新型强效双底物COMT抑制剂已被合成，这些抑制剂具有腺苷和儿茶酚结构单元。生物学结果显示，结合亲和力对抑制剂的预组织结构及核苷与儿茶酚单元间连接链的长度有较大依赖性。对COMT最有效的双底物抑制剂的IC50值为9 nM。它对SAM结合位点表现出竞争性动力学特性，而对儿茶酚结合位点则呈现出混合抑制动力学特征。其双底物结合模式通过分析抑制剂、COMT及Mg2+离子形成的三元复合物的X射线结构得到确认。
• Aminoacyl sulfamides for the treatment of hyperproliferative disorders
  申请人：Cubist Pharmaceuticals, Inc.

  公开号：US05824657A1

  公开（公告）日：1998-10-20

  Novel aminoacyl sulfamides are described. These compounds are effective in the treatment of hyperproliferative disorders, specifically psoriasis. Exemplary compounds of this invention are 5'-deoxy-adenosine 5'-N(N-L-phenylalanyl)sulfamide and 5'-deoxy-adenosine 5'-N-(N-L-tryptophanyl)sulfamide.

  小说氨酰磺胺已被描述。这些化合物在治疗过度增殖性疾病，特别是牛皮癣方面非常有效。本发明的示范化合物包括5'-去氧腺苷5'-N(N-L-苯丙氨酰)磺胺和5'-去氧腺苷5'-N-(N-L-色氨酰)磺胺。
• [EN] NOVEL ANTIBACTERIAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIBACTÉRIENS
  申请人：PASTEUR INSTITUT

  公开号：WO2012090136A1

  公开（公告）日：2012-07-05

  The present invention relates to compounds of formula (I): wherein Rj, R2, R3, R4, Xi, X2, X3 and Z are as defined in claim 1. The compounds are useful in the prevention and/or treatment of bacterial infections.

  本发明涉及以下化合物的公式(I)：其中R1、R2、R3、R4、X1、X2、X3和Z的定义如权利要求1所述。这些化合物在预防和/或治疗细菌感染方面具有用途。