(2R)-2-[(1R)-1-(6-氨基嘌呤-9-基)-2-氧代乙氧基]-3-羟基丙醛 | 39798-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: (2R)-2-[(1R)-1-(6-氨基嘌呤-9-基)-2-氧代乙氧基]-3-羟基丙醛
• 英文名称: Adenosine dialdehyde
• 英文别名: adenosine-2',3'-dialdehyde；AdOx；2-[1-(6-amino-purin-9-yl)-2-oxo-ethoxy]-3-hydroxy-propionaldehyde；(2R,4R)-2-(6-amino-purin-9-yl)-4-hydroxymethyl-3-oxa-glutaraldehyde；(2R,4R)-2-(6-Amino-purin-9-yl)-4-hydroxymethyl-3-oxa-glutaraldehyd；Adenox；(2R)-2-[(1R)-1-(6-aminopurin-9-yl)-2-oxoethoxy]-3-hydroxypropanal
• CAS: 39798-19-1
• 化学式: C₁₀H₁₁N₅O₄
• 分子量: 265.228
• InChiKey: ILMNSCQOSGKTNZ-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(1R)-1-(6-氨基嘌呤-9-基)-2-氧代乙氧基]-3-羟基丙醛 在 吡啶 、 potassium fluoride 、 sodium hydroxide 、 氨 、 乙酸酐 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (2R,3S,4R,5R,6R)-6-(6-aminopurin-9-yl)-2-(hydroxymethyl)-5-morpholin-4-yl-4-nitrooxan-3-ol
  参考文献：
  名称：

  Tsuboike, Kazunari; Mizuno, Gen; Minamoto, Katsumaro, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S45 - S48

  摘要：

  DOI：
• 作为产物：
  描述：

  腺苷 在 sodium periodate 作用下， 生成 (2R)-2-[(1R)-1-(6-氨基嘌呤-9-基)-2-氧代乙氧基]-3-羟基丙醛
  参考文献：
  名称：

  Davoll et al., Journal of the Chemical Society, 1946, p. 833,835

  摘要：

  DOI：

文献信息

• Heat-induced formation of .alpha.,.beta.-unsaturated nucleoside dialdehydes and their activity with adenosine deaminase
  作者：Alan J. Grant、Leon M. Lerner

  DOI：10.1021/jm00181a017

  日期：1980.7

  corresponding alpha,beta-unsaturated aldehydes. The reaction was first discovered during studies with adenosine deaminase and was initially investigated enzymatically until the nature of the chemical transformation was determined. A UV peak at 230-250 n, characteristic of the alpha,beta-unsaturated aldehyde group, was obtained by difference spectroscopy and affords a more practical means to study the reaction

  对核苷二醛（高碘酸盐氧化的核苷）的水溶液加热可得到相应的α，β-不饱和醛。该反应是在研究期间首次用腺苷脱氨酶发现的，并首先进行了酶学研究，直到确定了化学转化的性质。通过差示光谱法获得了在230-250n处具有α，β-不饱和醛基特征的UV峰，并提供了更实用的方法来研究该反应。通过腺苷的高碘酸盐氧化得到的腺苷二醛在加热时得到的产物与通过9-（5-脱氧-β-D-赤型-ent-4-烯呋喃糖基）腺嘌呤的高碘酸盐氧化得到的产物相同。通过用硼氢化钠还原这些化合物并比较彼此获得的二醇和与已知的不饱和二醇的比较，获得了进一步的身份证明。不建议在任何时候加热核苷二醛。在先前和当前的生物学研究中使用的核苷二醛的确切组成值得商question。
• Daunorubicin Derivatives Obtained from Daunorubicin and Nucleoside Dialdehydes
  作者：Eugenia N. Olsufyeva、Nikolai A. Brusentsov、Nedyalka Todorova、Jan Balzarini、Erik De Clercq、Maria N. Preobrazhenskaya

  DOI：10.1080/07328319708002524

  日期：1997.1

  Nucleoside dialdehydes were obtained by periodate oxidation of adenosine, cytidine, guanosine, uridine or 6-azauridine in the presence of Dowex (1x8; CH3COO-). Reductive alkylation of daunorubicin with these dialdehydes in the presence of NaBH3CN produced a series of 3'-deamino-3'-(4-morpholino)daunorubicin or 13-(R,S)-dihydrodaunorubicin derivatives, the latter being mixtures of two diastereomers at 13-C atom. The morpholino-daunorubicin derivatives containing nucleic base moieties are less cytotoxic than cyanomorpholino-daunorubicin, morpholino-daunorubicin and even than the parent antibiotic.
• Stereoselective Synthesis of Some 3-Nitroglucopyranosyladenine Analogues via a Nitroolefin: Intermediate as Potential Therapeutic Agents
  作者：Kazunari TSUBOIKE、Katsumaro MINAMOTO、Gen MIZUNO、Kazufumi YANAGIHARA

  DOI：10.1080/07328319808004672

  日期：1998.4

  Three isomers of 9-(4,6-O-benzylidene-3-deoxy-beta-D-hexopyranosyl) adenines (2-4) were isolated. The manno isomer 2 could be isomerized to the gluco isomer 3. The manno (2) and galacto isomer (4) were deprotected to 5 and 7, respectively. Michael addition of some organic amines and thiolates to the nitroolefin intermediate (8) gave the corresponding 2-(substituted)-3-nitro-glucopyranosides (9a-h). Compounds 9a,c,h were deprotected to l0a,c,h. Sodium azide with 8 gave the triazolo nucleoside 11, which was deprotected to 12. 2-Deoxy-3-nitro analogue 14 was also obtained.
• Adenosine dialdehyde analogs I: Regioselective synthesis of adenosine monoaldehydes
  作者：John P. Neenan、Sumittada M. Opitz、Charles L. Cooke、Michael A. Ussery、Terence C. Morrill、Linda M. Eckel

  DOI：10.1016/0960-894x(96)00234-x

  日期：1996.6

  Selective borohydride reduction of adenosine dialdehyde (1) gave the known adenosine 2'-monoaldehyde (2). Reaction of 1 with N,N'-diphenylethylenediamine, followed by reduction and deblocking gave adenosine 3'-monoaldehyde (5), a new compound. Unlike 2, compound 5 inhibited S-AdoHcy hydrolase and showed antiviral activity in vitro. Copyright (C) 1996 Elsevier Science Ltd