6-chloro-9-<5-O-benzoyl-2-deoxy-2-<(benzoyloxy)methyl>-β-D-ribofuranosyl>-9H-purine | 130469-45-3

• 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: 6-chloro-9-<5-O-benzoyl-2-deoxy-2-<(benzoyloxy)methyl>-β-D-ribofuranosyl>-9H-purine
• 英文别名: [(2R,3R,4S,5R)-5-(benzoyloxymethyl)-2-(6-chloropurin-9-yl)-4-hydroxyoxolan-3-yl]methyl benzoate
• CAS: 130469-45-3
• 化学式: C₂₅H₂₁ClN₄O₆
• 分子量: 508.918
• InChiKey: JXTRYSZISIYGEU-YGLGAKQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  125.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-chloro-9-<5-O-benzoyl-2-deoxy-2-<(benzoyloxy)methyl>-β-D-ribofuranosyl>-9H-purine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 12.08h， 生成 [(2R,3S,5S)-5-(benzoyloxymethyl)-2-(6-chloropurin-9-yl)oxolan-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：

  6-氯嘌呤 在 ammonium hydroxide 、 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 1.83h， 生成 6-chloro-9-<5-O-benzoyl-2-deoxy-2-<(benzoyloxy)methyl>-β-D-ribofuranosyl>-9H-purine
  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

• 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：——