9-(α-D-arabinofuranosyl)adenine | 3228-71-5

• 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: 9-(α-D-arabinofuranosyl)adenine
• 英文别名: 9-α-D-arabinofuranosyl-adenine；9-α-D-arabinofuranosyladenine；α-D-arabinoadenosine；1-(6-amino-purin-9-yl)-α-D-1-deoxy-arabinofuranose；(1S)-1-(6-Amino-purin-9-yl)-1,4-anhydro-D-arabit；9-a-arabinofuranosyl adenine；(2S,3S,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2S,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 3228-71-5
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: OIRDTQYFTABQOQ-KMPDEGCQSA-N

物化性质

• 物理描述：
  Vidarabine is a white to off-white crystalline powder. (NTP, 1992)
• 颜色/状态：
  Crystals from water
• 熔点：
  257.0-257.5 °C (0.4 H2O)
• 溶解度：
  In water, 8.23X10+3 mg/L at 25 °C (est)
• 蒸汽压力：
  6.0X10-15 mm Hg at 25 °C (est)
• 稳定性/保质期：
  Vidarabine ophthalmic ointment should be stored at a temperature less than 40 °C, preferably between 15-30 °C; freezing should be avoided.
• 旋光度：
  Specific optical rotation: -5 deg at 27 °C/D (concentration by volume= 0.25 g in 100 ml water).
• 分解：
  When heated to decomposition it emits very toxic fumes of /nitrogen oxides/.

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 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：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(α-D-arabinofuranosyl)adenine 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 88.0h， 生成 N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-3-O-succinoyl-α-D-arabinofuranosyl}adenine
  参考文献：
  名称：

  Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides

  摘要：

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.

  DOI：

  10.1080/15257770500267113
• 作为产物：
  描述：

  N⁶-benzoyl-9-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)adenine 在 氨 作用下， 以 甲醇 为溶剂， 反应 28.0h， 以67%的产率得到9-(α-D-arabinofuranosyl)adenine
  参考文献：
  名称：

  Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides

  摘要：

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.

  DOI：

  10.1080/15257770500267113

文献信息

• The nucleoside transport proteins, NupC and NupG, from Escherichia coli: specific structural motifs necessary for the binding of ligands
  作者：Simon G. Patching、Stephen A. Baldwin、Alexander D. Baldwin、James D. Young、Maurice P. Gallagher、Peter J. F. Henderson、Richard B. Herbert

  DOI：10.1039/b414739a

  日期：——

  unrelated transporters showed similar but distinct patterns of inhibition, revealing differing selectivities for the different nucleosides and their analogues. Binding of nucleosides to NupG required the presence of hydroxyl groups at each of the C-3' and C-5' positions of ribose, while binding to NupC required only the C-3' hydroxyl substituent. The greater importance of the ribose moiety for binding to

  测试了一系列46种天然核苷和类似物（主要是基于腺苷的）作为从大肠杆菌中富集的，与H（+）连接的核苷转运蛋白NupC和NupG吸收[U-（14）C]尿苷的抑制剂。这两个在进化上不相关的转运蛋白显示出相似但不同的抑制模式，揭示了对不同核苷及其类似物的不同选择性。核苷与NupG的结合需要在核糖的C-3'和C-5'位置分别存在羟基，而与NupC的结合仅需要C-3'羟基取代基。核糖部分对于结合NupG的重要性更高，与该蛋白质和寡糖之间的进化关系一致：运输者的主要促进者超家族（MFS）的H（+）同向转运蛋白（OHS）亚家族。对于两种蛋白质，C-3'处的天然α-构型和C-1'处的天然β-构型对于配体结合都是必需的。发现腺苷的咪唑环中的N-7和C-6的氨基对于结合并不重要，并且两个转运蛋白都显示出C-6 / N取代的灵活性。N-1和N-3中的一个或两个对腺苷类似物与NupC的结合很重要，但对NupG的结合
• Generation of C-1′ radicals through a β-(acyloxy)alkyl rearrangement in modified purine and pyrimidine nucleosides
  作者：Thanasis Gimisis、Giuseppina Ialongo、Chryssostomos Chatgilialoglu

  DOI：10.1016/s0040-4020(97)10317-9

  日期：1998.1

  12 with tributyltin hydride generates indirectly C-1′ radicals through a β-(acyloxy)alkyl rearrangement. Rate constants for these rearrangements have been measured by using free-radical clock methodology and comparison of these data with previous reported results provides structural information about the nature of this important class of radicals.

  受保护的1'，2'-二氢-2'-脱氧腺苷的合成已通过结合对腺嘌呤氨基官能团的亚磷叉基保护进行了优化。这些不饱和腺苷已用作亲电子碘新戊酰氧基化的底物，导致在异头位置被修饰的新核苷。卤代戊二酸酯10、11和12与氢化三丁基锡的反应通过β-（酰氧基）烷基重排间接产生C-1'自由基。这些重排的速率常数已通过使用自由基时钟方法进行了测量，并将这些数据与先前报道的结果进行比较可提供有关这一重要基团性质的结构信息。
• Mutant purine nucleoside phosphorylase proteins and cellular delivery thereof
  申请人：Ealick E. Steven

  公开号：US20050214901A1

  公开（公告）日：2005-09-29

  A host cell stably transformed or transfected by a vector including a DNA sequence encoding for mutant purine nucleoside cleavage enzymes is provided. The transformed or transfected host cell can be used in combination with a purine substrate to treat tumour cells and/or virally infected cells. A nucleotide sequence encoding mutant E. coli derived purine nucleoside phosphorylase proteins which can be used in conjunction with an appropriate substrate to produce toxins which impair abnormal cell growth is also provided. A method is detailed for the delivery of toxin by generation withing target cells or by administration and delivery to the cells from without. Novel purine nucleosides are detailed that yield a cytotoxic purine upn enzymatic cleavage. A synthetic process for nucleosides is also detailed.

  提供了一种由载有突变嘌呤核苷酸裂解酶编码DNA序列的载体转化或转染的宿主细胞。该转化或转染的宿主细胞可与嘌呤底物结合，用于治疗肿瘤细胞和/或病毒感染的细胞。还提供了编码突变E. coli来源的嘌呤核苷酰化酶蛋白的核苷酸序列，可与适当的底物结合使用，产生有害细胞生长的毒素。详细介绍了一种通过靶细胞内生成或通过外部给药和传递给细胞的毒素递送方法。详细介绍了产生细胞毒性嘌呤核苷酶裂解产物的新型嘌呤核苷。还详细介绍了一种核苷的合成过程。
• Novel adenine nucleoside derivatives, their preparation and pharmaceutical compositions containing them
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：EP0042596A1

  公开（公告）日：1981-12-30

  Disclosed herein are novel adenine nucleoside derivatives of the general formula I and the pharmaceutically acceptable salts thereof, wherein Q represents oxygen or methylene and Rx, Ry and Rz independently represent hydrogen or an alkoxyalkanoyl grouping R1-O-R2-CO-, with the proviso that at least one of Rx, Ry and Rz is the alkoxyalkanoyl grouping R1-O-R2-CO-, the alkyl moiety R1 and the alkadiyl moiety R2 each independently containing 1 to 6 carbon atoms. The novel compounds exhibit antiviral activity and their use forthis purpose is disclosed. Also disclosed are methods for the preparation of the novel compounds and pharmaceutical compositions containing them.

  本文公开了通式 I 的新型腺嘌呤核苷衍生物及其药物可接受盐。 及其药学上可接受的盐，其中 Q 代表氧或亚甲基，Rx、Ry 和 Rz 独立地代表氢或烷氧基烷酰基 R1-O-R2-CO-，但 Rx、Ry 和 Rz 中至少有一个是烷氧基烷酰基 R1-O-R2-CO-，烷基 R1 和烷二基 R2 各自独立地含有 1 至 6 个碳原子。 这些新型化合物具有抗病毒活性，其用途也已公开。此外，还公开了新型化合物的制备方法和含有这些化合物的药物组合物。
• Nucleoside 5'-alkyl- or alkenylphosphate
  申请人：Yamasa Shoyu Kabushiki Kaisha

  公开号：EP0097376A1

  公开（公告）日：1984-01-04

  Nucleoside 5'-alkyl- or alkenyl phosphate compounds represented by the following formula [I] wherein B is a purine base having a substituent or a 5-substituted uracil base, and R' is an alkyl or alkenyl group having 14 to 26 carbon atoms, and pharmaceutically acceptable salts thereof are novel derivatives of arabinonucleosides which can have properties suitable for clinical application as antiviral agents, particularly for treating viral hepatitis.

  由下式[I]代表的核苷 5'-烷基-或烯基磷酸酯化合物 其中 B 是具有取代基的嘌呤基或 5-取代的尿嘧啶基，R'是具有 14 至 26 个碳原子的烷基或烯基，及其药学上可接受的盐是阿拉伯核苷的新型衍生物，其特性适合作为抗病毒药物，特别是用于治疗病毒性肝炎的临床应用。