5,7-dichloro-3-(3-deoxy-α-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine | 232277-35-9

• 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: 5,7-dichloro-3-(3-deoxy-α-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
• 英文别名: (2S,3R,5S)-2-(5,7-dichloroimidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)oxolan-3-ol
• CAS: 232277-35-9
• 化学式: C₁₁H₁₁Cl₂N₃O₃
• 分子量: 304.133
• InChiKey: VBONQOYZXVGKTH-MJIFXRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-dichloro-3-(3-deoxy-α-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine 在 palladium on activated charcoal sodium hydroxide 、 氨 、 氢气 作用下， 以 乙醇 为溶剂， 120.0 ℃ 、275.79 kPa 条件下， 反应 18.0h， 生成 7-amino-3-(3-deoxy-α-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis and Adenosine Deaminase Inhibitory Activity of 3′-Deoxy-1-deazaadenosines

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2112::aid-hlca2112>3.0.co;2-2
• 作为产物：
  描述：

  3-(2-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranosyl)-5,7-dichloro-3H-imidazo[4,5-b]pyridine 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以56%的产率得到5,7-dichloro-3-deoxy-3-deoxy-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis and Adenosine Deaminase Inhibitory Activity of 3′-Deoxy-1-deazaadenosines

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2112::aid-hlca2112>3.0.co;2-2

文献信息

• 3′-DEOXYRIBOFURANOSE DERIVATIVES OF 1-DEAZA AND 3-DEAZA-ADENOSINE AND THEIR ACTIVITY AS ADENOSINE DEAMINASE INHIBITORS
  作者：S. Costanzi、C. Lambertucci、R. Volpini、S. Vittori、G. Lupidi、G. Cristalli

  DOI：10.1081/ncn-100002486

  日期：2001.3.31

  2,6-Dichloro-1-deazapurine and 2,6-dichloro-3-deazapurine were coupled with 1,2-O-diacetyl-5-O-benzoyl-3-deoxy-beta -D-ribofuranose. Deprotection of the obtained compounds and reaction with liquid ammonia gave the desired 2-chloroadenine nucleosides, which were dechlorinated to afford the corresponding 1-deaza and 3-deazaadenosine derivatives. Biological studies performed on ADA from calf intestine showed that these new nucleosides are inhibitors of the enzyme.
• Coupling of 2,6-Dichloropurine and 2,6-Dichlorodeazapurines with Ribose and Ribose Modified Sugars
  作者：S. Vittori、E. Camaioni、S. Costanzi、R. Volpini、G. Cristalli

  DOI：10.1080/15257779908041503

  日期：1999.4

  Substituted purine and deazapurine nucleosides are of great interest in medicinal chemistry. Furthermore, 3'-deoxynucleosides exhibit a number of biological activities. In this research the coupling of 2,6-dichloro-1- or 3-deazapurine with protected 3'-deoxyribose is reported. Depending upon coupling conditions and base structure, different anomeric and isomeric mixtures have been obtained. Extensive studies, utilizing chemical and physical methods, have been performed to assign the correct configuration to the resulting nucleosides.