4-(adenin-9-yl)-2,3-isopropylidenedioxybutanal | 184227-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4-(adenin-9-yl)-2,3-isopropylidenedioxybutanal
• 英文别名: (4S,5S)-5-[(6-aminopurin-9-yl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 184227-81-4
• 化学式: C₁₂H₁₅N₅O₃
• 分子量: 277.283
• InChiKey: IPXAKRZJVHWOTO-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 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：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(adenin-9-yl)-2,3-isopropylidenedioxybutanal 在 sodium hydroxide 、 sodium tetrahydroborate 、 水 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 28.0h， 生成 (3S)-4-(6-aminopurin-9-yl)-2-(hydroxymethyl)butane-1,2,3-triol
  参考文献：
  名称：

  Novel synthesis of purine acyclonucleosides possessing a chiral 9-hydroxyalkyl group by sugar modification of 9-D-ribitylpurines

  摘要：

  利用 9-(2,3-O-异亚丙基-D-核苷)嘌呤 1，合成了一种在 N9-羟基烷基链中具有手性碳的嘌呤无环核苷的新方法，这种嘌呤核苷很容易从市售的嘌呤核苷中制备出来。9-[(2S,3R)-2,3,4-三羟丁基]嘌呤 4a 和 4b、9-[(2S,3S)-2,3,4-三羟丁基]嘌呤 6a 和 6b、L-丝裂腺嘌呤 8、及其类似物 11 可通过关键的中间体（(2S,3S)-2,3-异亚丙基二氧基-4-(嘌呤-9-基)丁醛 2 通过二元醇 1 的 NaIO4 氧化反应制备）方便地合成。

  DOI：

  10.1039/a707193k
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 sodium periodate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 27.0h， 生成 4-(adenin-9-yl)-2,3-isopropylidenedioxybutanal
  参考文献：
  名称：

  Synthesis and biological activity of novel S-Adenosyl-l-homocysteine hydrolase inhibitors

  摘要：

  Four potential S-adenosyl-L-homocysteine hydrolase inhibitors were prepared and tested against purified recombinant rat liver enzyme. Preliminary studies indicate that three of these compounds, 1, 2, and 4, caused time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase but showed a biphasic nature. Compound 3 was found to be a rapid equilibrium inhibitor of this enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00301-8

文献信息

• A Novel Approach for the Synthesis of Purine Acyclonucleosides Using 9-D-Ribitylpurines as a Chiral Pool
  作者：Kosaku Hirota、Yasunari Monguchi、Hironao Sajiki、Yukio Kitade

  DOI：10.1055/s-1997-3273

  日期：1997.6

  Facile syntheses of L-eritadenine (8a), (2S,3R)-9-(2,3,4-trihydroxybutyl)purines (4a and 4b), and (2S,3S)-9-(2,3,4-trihydroxybutyl)adenine (6a) were achieved by using 9-D-(2,3-O-isopropylideneribityl)purines (1a and 1b) as a chiral pool

  轻松合成 L-eritadenine (8a)、(2S,3R)-9-(2,3,4-三羟基丁基)嘌呤（4a 和 4b）和 (2S,3S)-9-(2,3,4-)三羟基丁基）腺嘌呤（6a）是通过使用 9-D-（2,3-O-异亚丙基二联基）嘌呤（1a 和 1b）作为手性池获得的
• 9-[(2′S,3′S)-3′-formyl-2′,3′-dihydroxypropyl]adenine: A facile affinity-labeling probe of human hydrolase
  作者：Yukio Kitade、Masayuki Nakanishi、Chizuko Yatome

  DOI：10.1016/s0960-894x(99)00470-9

  日期：1999.9

  Treatment of human recombinant S-adenosyl-L-homocysteine (SAH) hydrolase with 9-[(2'S,3'S)-3'-formyl-2',3'-dihydroxypropyl]adenine (FDHPA) caused irreversible inactivation in a time- and concentration-dependent manner (K-i = 8.8 mu M, k(inact) = 0.09 min(-1)).. FDHPA behaved as a facile affinity-labeling probe of SAH hydrolase. (C) 1999 Elsevier Science Ltd. Air rights reserved.
• A Convenient Synthesis of Acyclic Adenosines with an Unsaturated Side Chain by Modification of 9-(2,3-<i>O</i>-Isopropylidene-D-Ribityl)Adenine
  作者：Kosaku Hirota、Yasunari Monguchi、Hironao Sajiki、Chizuko Yatome、Akio Hiraoka、Yukio Kitade

  DOI：10.1080/07328319808003472

  日期：1998.8

  In expectation of discovering their antiviral activity, acyclic adenosine derivatives 7, 11, 12, and 16 were designed as analogs of neplanocin A (NPA) and L-eritadenine which are strong inhibitors of S-adenosyl-L-homocysteine hydrolase. The 1',5'-seco-analog of 4'-deoxymethyl-NPA (DHCA) 7 was synthesized by dideoxygenation of 9-(2, 3-O-isopropylidene-D-ribityl)adenine (2). Acyclic DHCA analogs 11 and 16 were obtained by Wittig reaction of the aldehyde 3 with Ph3P=CHCO2Et and Ph3P=CHCN, respectively. Hydrolysis of the ester 11 afforded a vinylog of L-eritadenine 12. The synthesized acyclic nucleosides 7, 10, and 11 were evaluated for antiviral activity, however, none of them showed any significant antiviral activity.
• Novel synthesis of purine acyclonucleosides possessing a chiral 9-hydroxyalkyl group by sugar modification of 9-D-ribitylpurines
  作者：Kosaku Hirota、Yasunari Monguchi、Hironao Sajiki、Magoichi Sako、Yukio Kitade

  DOI：10.1039/a707193k

  日期：——

  A novel approach to the synthesis of purine acyclonucleosides having chiral carbons in the N9-hydroxyalkyl chain was achieved by using 9-(2,3-O-isopropylidene-D-ribityl)purines 1, which are readily prepared from commercially available purine nucleosides. 9-[(2S,3R)-2,3,4-Trihydroxybutyl]purines 4a and 4b, 9-[(2S,3S)-2,3,4-trihydroxybutyl]purines 6a and 6b, L-eritadenine 8, and its analogue 11 are conveniently synthesized via key intermediates, (2S,3S)-2,3-isopropylidenedioxy-4-(purin-9-yl)butanals 2 prepared by NaIO4 oxidation of diols 1.

  利用 9-(2,3-O-异亚丙基-D-核苷)嘌呤 1，合成了一种在 N9-羟基烷基链中具有手性碳的嘌呤无环核苷的新方法，这种嘌呤核苷很容易从市售的嘌呤核苷中制备出来。9-[(2S,3R)-2,3,4-三羟丁基]嘌呤 4a 和 4b、9-[(2S,3S)-2,3,4-三羟丁基]嘌呤 6a 和 6b、L-丝裂腺嘌呤 8、及其类似物 11 可通过关键的中间体（(2S,3S)-2,3-异亚丙基二氧基-4-(嘌呤-9-基)丁醛 2 通过二元醇 1 的 NaIO4 氧化反应制备）方便地合成。
• Synthesis and biological activity of novel S-Adenosyl-l-homocysteine hydrolase inhibitors
  作者：Jennifer A Steere、John F Honek

  DOI：10.1016/s0968-0896(03)00301-8

  日期：2003.7

  Four potential S-adenosyl-L-homocysteine hydrolase inhibitors were prepared and tested against purified recombinant rat liver enzyme. Preliminary studies indicate that three of these compounds, 1, 2, and 4, caused time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase but showed a biphasic nature. Compound 3 was found to be a rapid equilibrium inhibitor of this enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.