4,6-dichloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine | 220249-18-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 4,6-dichloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine
• 英文别名: (2S,3R,5S)-2-(4,6-dichloroimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolan-3-ol
• CAS: 220249-18-3
• 化学式: C₁₁H₁₁Cl₂N₃O₃
• 分子量: 304.133
• InChiKey: QMMOYNWKMSIDGP-MJIFXRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：

  4,6-dichloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine 在 镍 一水合肼 作用下， 以 水 为溶剂， 反应 6.0h， 生成 4-amino-6-chloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine
  参考文献：
  名称：

  Synthesis of New 3′-Deoxyribonucleosides Employing the Acid-Catalyzed Fusion Method

  摘要：

  Coupling of 4,6-dichloro-1H-imidazo[4,5-c]pyridine (2.6-dichloro-3-deaza-9H-purine) (I) with 1,2-O-diacetyl-5-O-benzoyl-3-deoxy-beta-D-ribofuranose (2), employing the acid-catalyzed fusion method, is reported (Scheme I). The condensation reaction was regioselective and gave the three N-1-glycosylation products 3-5, whereas no N-3-nucleosides were detected. Treatment of 3-5 with methanolic ammonia afforded the corresponding deprotected nucleosides 6-8. Compounds 6 and 7 were assigned the structure of the beta-D- and alpha-D-anomeric N-1-(3'-deoxyribo)nucleosides, respectively. The third derivative 8 proved to be the alpha-D-anomer of a 3'-deoxyarabinonucleoside deriving from epimerization at C(2) of the sugar. The 2-chloro- and N-6-substituted derivatives 9, 11, and 13 of 3'-decxy-3-deazaadenosine (10) and of its alpha-D-anomer 12 can be obtained from these versatile synthons (Schemes 2 and 3).

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2326::aid-hlca2326>3.0.co;2-4
• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose 在 氨 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 4,6-dichloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine
  参考文献：
  名称：

  Purine and deazapurine nucleosides: synthetic approaches, molecular modelling and biological activity

  摘要：

  A number of ligands for the adenosine binding sites has been obtained by using nucleoside convergent and divergent synthesis. Most of our nucleosides have been synthesized by coupling 2,6-dichloropurine (1), 2,6-dichloro-1-deazapurine (2), 2,6-dichloro-3-deazapurine (3) with ribose, 2- and 3-deoxyribose and 2,3-dideoxyribose derivatives. The use of these versatile synthons allowed the introduction of various substituents in 2- and/or 6-positions. The glycosylation site and the anomeric configuration of the obtained nucleosides were assigned on the basis of spectroscopic studies and confirmed by molecular models. A series of potent adenosine receptor ligands has been obtained by using divergent approaches, mostly starting from guanosine. Substitutions in 2, 6, 8, and 5' position of adenosine molecule led to ligands selective for the different adenosine receptor subtypes. Furthermore, we investigated the molecular bases of the different behavior of 2- and 8-alkynyl adenosines, by means of NMR experiments and molecular modeling studies. With docking experiments, we demonstrated that the two class of molecules should have different binding modes that explain their different degree of affinity and the shift of their activity from agonistic (2-substituted derivatives) to antagonistic (8-substituted derivatives).

  DOI：

  10.1016/s0014-827x(03)00019-3

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.