9-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>adenine | 130469-53-3

• 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: 9-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>adenine
• 英文别名: 9-[(2R,4R,5S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-amine
• CAS: 130469-53-3
• 化学式: C₂₃H₄₃N₅O₃Si₂
• 分子量: 493.797
• InChiKey: AQIUHCLFGQHQCV-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  97.31
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  9-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>adenine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以66%的产率得到9-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>adenine
  参考文献：
  名称：

  A ring-enlarged oxetanocin A analog as an inhibitor HIV infectivity

  摘要：

  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.

  DOI：

  10.1021/jm00105a054
• 作为产物：
  描述：

  6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 氨 、 三正丁基氢锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 67.0h， 生成 9-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>adenine
  参考文献：
  名称：

  A ring-enlarged oxetanocin A analog as an inhibitor HIV infectivity

  摘要：

  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.

  DOI：

  10.1021/jm00105a054

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。
• 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：——