3-deoxy-3-<(benzoyloxy)methyl>-1,2-isopropylidene-α-ribofuranose | 130469-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-deoxy-3-<(benzoyloxy)methyl>-1,2-isopropylidene-α-ribofuranose
• 英文别名: [(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]methyl benzoate
• CAS: 130469-48-6
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: XNTWGDAQENWZRZ-RGCMKSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-<(benzoyloxy)methyl>-1,2-isopropylidene-α-ribofuranose 在 吡啶 、 Bio-Rad AG 50W-X₈ (H⁺) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 37.0h， 生成 [(2S,3S,4R)-2-(benzoyloxymethyl)-4,5-dihydroxyoxolan-3-yl]methyl benzoate
  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：

  ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-deoxy-3-<(benzoyloxy)methyl>-1,2-isopropylidene-α-ribofuranose
  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

• NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT
  申请人：Chen James M.

  公开号：US20100104532A1

  公开（公告）日：2010-04-29

  The invention provides unsaturated phosphonates of Formula I or a tautomer or pharmaceutically accepatble salt thereof, as described herein, as well as pharmaceutical compositions comprising the compounds, and therapeutic methods comprising administering the compounds. The compounds have anti-viral properties and are useful for treating viral infections (e.g. HCV) in animals (e.g. humans).

  本发明提供了公式I或其互变异构体或药学上可接受的盐的不饱和膦酸酯，以及包含这些化合物的制药组合物和包括给予这些化合物的治疗方法。这些化合物具有抗病毒性质，适用于治疗动物（如人类）的病毒感染（例如HCV）。
• Chimera of Dimethylene Sulfone-, Methyl Sulfide-, and Methyl Sulfoxide-Linked Ribonucleotides and DNA
  作者：Daniel K. Baeschlin、Birgitte Hyrup、Steven A. Benner、Clemens Richert

  DOI：10.1021/jo960669h

  日期：1996.1.1
• 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：——
• US8324179B2
  申请人：——

  公开号：US8324179B2

  公开（公告）日：2012-12-04
• 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.