9-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>adenine | 130469-38-4

• 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-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>adenine
• 英文别名: 6-amino-9-<2,3-dideoxy-3-(hydroxymethyl)-β-D-ribofuranosyl>-9H-purine；2-C-(adenin-9-yl)-1,4-anhydro-2,3-dideoxy-3-C-hydroxymethyl-D-arabino-pentitol；6-amino-9-[2,3-dideoxy-3-(hydroxymethyl)-β-D-ribofuranosyl]-9H-purine；Adenosine, 2',3'-dideoxy-3'-(hydroxymethyl)；[(2S,3R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]methanol
• CAS: 130469-38-4
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: ROKFTZONUGKALY-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-氯嘌呤 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 9-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>adenine
  参考文献：
  名称：

  2'，3'-二脱氧-3'-C-羟甲基核苷的合成及HIV抑制活性。

  摘要：

  基于手性环丁酮前体（2S）-反式2,3-双[（苯甲酰氧基）甲基]的光化学扩环，制备了一系列2'，3'-二脱氧-3'-C-羟甲基嘌呤核苷环丁酮，在6-取代的嘌呤存在下。在这种转化中，α-和β-端基异构体均产生。通过光加合物与饱和甲醇氨的反应进行脱保护。测试了九种嘌呤核苷对HIV IIIB病毒对H9细胞的抑制作用。6-己氧基和腺嘌呤衍生物4e，c似乎在抑制病毒繁殖方面最有效，而4c的活性与ddI和AZT相当。

  DOI：

  10.1021/jm950822k

文献信息

• The synthesis of novel 3′,5′-homocyclic nucleotides as potential anti-HIV agents
  作者：Michael G. B. Drew、Stephen Gorsuch、Jayne H. M. Gould、John Mann

  DOI：10.1039/a900800d

  日期：——

  (5S)-(5-tert-Butyldimethylsiloxymethyl)furan-2(5H)-one has been converted into cytosine 2′,3′-dideoxy-3′,5′-homocyclic monophosphate (and its 5-fluoro congener) together with an adenosine homocyclic monophosphate. These were designed as inhibitors of HIV reverse transcriptase although they did not possess such activity.

  (5S)-(5-叔丁基二甲基硅氧基甲基)呋喃-2(5H)-酮已被转化为胞苷2′,3′-二脱氧-3′,5′-同环单磷酸（及其5-氟同系物）和腺苷同环单磷酸。这些分子被设计为HIV逆转录酶的抑制剂，尽管它们并不具备此种活性。
• Ohrui, Hiroshi; Waga, Toshiaki; Meguro, Hiroshi, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 6, p. 1040 - 1042
  作者：Ohrui, Hiroshi、Waga, Toshiaki、Meguro, Hiroshi

  DOI：——

  日期：——
• A ring-enlarged oxetanocin A analog as an inhibitor HIV infectivity
  作者：Christopher K. H. Tseng、Victor E. Marquez、George W. A. Milne、Ronald J. Wysocki、Hiroaki Mitsuya、Takuma Shirasaki、John S. Driscoll

  DOI：10.1021/jm00105a054

  日期：1991.1

  Two ring-expanded analogues (compounds 2 and 3) of the anti-HIV fermentation product oxetanocin A (1) were synthesized from commercially available diacetone D-glucose. Antiviral testing against HIV in ATH8 cells revealed that the ring-expanded analogue 2 possessed a similar activity profile as oxetanocin A. Neither compound, however, was capable of providing full protection to the cells against HIV infection. The isomeric ring-expanded analogue 3 was totally devoid of anti-HIV activity. Molecular modeling suggested that while oxetanocin A and compounds 2 and 3 share a large common substructure with the potent anti-HIV drug, dideoxyadenosine (ddA), the extra hydroxymethyl substituent may contribute negatively to the binding of these molecules to a critical enzyme. The negative contribution may be less important in oxetanocin and isomer 2 than in isomer 3. From these studies it would appear that both oxetane and tetrahydrofuran rings are equivalent templates to support the adenine base in terms of anti-HIV activity.
• Synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides as potential inhibitors of HIV
  作者：Lars Svansson、Ingemar Kvarnstroem、Bjoern Classon、Bertil Samuelsson

  DOI：10.1021/jo00009a012

  日期：1991.4

  A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromobenzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give the requisite methyl furanoside derivative 5, which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the alpha- and beta-nucleoside analogues.
• TSENG, CHRISTOPHER K. -H.;MARGUEZ, VICTOR E.;MILNE, GEORGE W. A.;WYSOCKI,+, J. MED. CHEM., 34,(1991) N, C. 343-349
  作者：TSENG, CHRISTOPHER K. -H.、MARGUEZ, VICTOR E.、MILNE, GEORGE W. A.、WYSOCKI,+

  DOI：——

  日期：——