1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine | 220249-14-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine
• 英文别名: [(2S,4R,5R)-4-acetyloxy-5-(4,6-dichloroimidazo[4,5-c]pyridin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 220249-14-9
• 化学式: C₂₀H₁₇Cl₂N₃O₅
• 分子量: 450.278
• InChiKey: RREOHWZIJJNYSK-ZBQZNYHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.54
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine 在 氨 作用下， 以 甲醇 为溶剂， 生成 4-amino-6-chloro-1-(3-deoxy-β-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine
  参考文献：
  名称：

  3′-DEOXYRIBOFURANOSE DERIVATIVES OF 1-DEAZA AND 3-DEAZA-ADENOSINE AND THEIR ACTIVITY AS ADENOSINE DEAMINASE INHIBITORS

  摘要：

  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.

  DOI：

  10.1081/ncn-100002486
• 作为产物：
  描述：

  4,6-二氯-1H-咪唑并[4,5-c]吡啶 、 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose 在 四氯化锡 作用下， 以 乙腈 为溶剂， 以27%的产率得到1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine
  参考文献：
  名称：

  3′-DEOXYRIBOFURANOSE DERIVATIVES OF 1-DEAZA AND 3-DEAZA-ADENOSINE AND THEIR ACTIVITY AS ADENOSINE DEAMINASE INHIBITORS

  摘要：

  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.

  DOI：

  10.1081/ncn-100002486

文献信息

• 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.
• Synthesis of New 3′-Deoxyribonucleosides Employing the Acid-Catalyzed Fusion Method
  作者：Rosaria Volpini、Emidio Camaioni、Stefano Costanzi、Sauro Vittori、Gloria Cristalli

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2326::aid-hlca2326>3.0.co;2-4

  日期：1998.12.16

  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).