5,7-dichloro-3-deoxy-3-deoxy-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine | 232277-32-6

• 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-deoxy-3-deoxy-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine
• 英文别名: 5,7-dichloro-3-(3-deoxy-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine；(2R,3R,5S)-2-(5,7-dichloroimidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)oxolan-3-ol
• CAS: 232277-32-6
• 化学式: C₁₁H₁₁Cl₂N₃O₃
• 分子量: 304.133
• InChiKey: VBONQOYZXVGKTH-AODONOJDSA-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-deoxy-3-deoxy-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine 在 palladium on activated charcoal 氨 、 氢气 作用下， 生成 7-amino-3-(3-deoxy-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Potent and Selective Ligands for Adenosine Binding Sites

  摘要：

  A number of selective ligands for the different binding sites of adenosine have been synthesized and tested in several pharmacological models. The aim of these synthetic efforts is both to improve the knowledge of structure-activity relationships in the adenosine-related biological systems and to develop drugs from some of these molecules.

  DOI：

  10.1080/07328319708006189
• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose 在 氨 、 四氯化锡 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 5,7-dichloro-3-deoxy-3-deoxy-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Coupling of 2,6-Dichloropurine and 2,6-Dichlorodeazapurines with Ribose and Ribose Modified Sugars

  摘要：

  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.

  DOI：

  10.1080/15257779908041503

文献信息

• Synthesis and Adenosine Deaminase Inhibitory Activity of 3′-Deoxy-1-deazaadenosines
  作者：Rosaria Volpini、Stefano Costanzi、Sauro Vittori、Gloria Cristalli、Giulio Lupidi

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

  日期：1999.12.15
• 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.