2,6,7-Trichloro-3-(2,3-dideoxy-2-iodo-β-D-ribofuranosyl)imidazo[1,2-a]pyridine | 194228-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2,6,7-Trichloro-3-(2,3-dideoxy-2-iodo-β-D-ribofuranosyl)imidazo[1,2-a]pyridine
• 英文别名: [(2S,4R,5S)-4-iodo-5-(2,6,7-trichloroimidazo[1,2-a]pyridin-3-yl)oxolan-2-yl]methanol
• CAS: 194228-89-2
• 化学式: C₁₂H₁₀Cl₃IN₂O₂
• 分子量: 447.487
• InChiKey: TYRUWRFRMALMIM-UHQICPFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6,7-Trichloro-3-(2,3-dideoxy-2-iodo-β-D-ribofuranosyl)imidazo[1,2-a]pyridine 在 四氧化锇 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 32.0h， 生成 2,6,7-Trichloro-3-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis of the First C3 Ribosylated Imidazo[1,2-a]pyridine C-Nucleoside by Enantioselective Construction of the Ribose Moiety

  摘要：

  The metabolic instability of the glycosidic linkage in 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole prompted us to synthesize the structurally related C-nucleoside 2,6,7-trichloro-3-(beta-D-ribofuranosyl)imidazo[1,2-a]pyridine. Synthesis of this first C3-ribofuranosylimidazo[1,2-a]pyridine was accomplished by developing a modification of existing iodocyclization methodology for obtaining a 1',4'-syn furanosyl precursor, without an extensive protection scheme. This 1',4'-syn precursor was elaborated inter the desired ribofuranosyl C-nucleoside. X-ray crystallography was used to unambiguously determine structure and absolute stereochemistry of this C-nucleoside.

  DOI：

  10.1021/jo9711145
• 作为产物：
  描述：

  2,6,7-Trichloro-3-(1,2(S)-dihydroxy-pent-4(E)-en-5-yl)imidazo[1,2-a]pyridine 在 碘 、 potassium carbonate 作用下， 生成 (3S,5S,6R)-5-Iodo-6-(2,6,7-trichloro-imidazo[1,2-a]pyridin-3-yl)-tetrahydro-pyran-3-ol 、 2,6,7-Trichloro-3-(2,3-dideoxy-2-iodo-β-D-ribofuranosyl)imidazo[1,2-a]pyridine 、 [(2S,4S,5R)-4-Iodo-5-(2,6,7-trichloro-imidazo[1,2-a]pyridin-3-yl)-tetrahydro-furan-2-yl]-methanol
  参考文献：
  名称：

  Synthesis of the First C3 Ribosylated Imidazo[1,2-a]pyridine C-Nucleoside by Enantioselective Construction of the Ribose Moiety

  摘要：

  The metabolic instability of the glycosidic linkage in 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole prompted us to synthesize the structurally related C-nucleoside 2,6,7-trichloro-3-(beta-D-ribofuranosyl)imidazo[1,2-a]pyridine. Synthesis of this first C3-ribofuranosylimidazo[1,2-a]pyridine was accomplished by developing a modification of existing iodocyclization methodology for obtaining a 1',4'-syn furanosyl precursor, without an extensive protection scheme. This 1',4'-syn precursor was elaborated inter the desired ribofuranosyl C-nucleoside. X-ray crystallography was used to unambiguously determine structure and absolute stereochemistry of this C-nucleoside.

  DOI：

  10.1021/jo9711145

文献信息

• US6214801B1
  申请人：——

  公开号：US6214801B1

  公开（公告）日：2001-04-10
• [EN] IMIDAZO[1,2-A]PYRIDINE C-NUCLEOSIDES AS ANTIVIRAL AGENTS<br/>[FR] IMIDAZO[1,2-A]PYRIDINE C-NUCLEOSIDES COMME AGENTS ANTIVIRAUX
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：WO1997027205A1

  公开（公告）日：1997-07-31

  (EN) This invention pertains to nucleoside analogs which have antiviral activity and improved metabolic stability, compositions comprising them, and methods of antiviral treatment employing them. More particularly, this invention pertains to imidazo [1,2-a]pyridine C-nucleosides, as exemplified by compounds such imidazo[1,2-a]pyridine C5-nucleosides and imidazo[1,2-a]pyridine C3-nucleosides, and may be represented by formula (I), wherein exactly one of Q3 and Q5 is a sugar-like moiety; exactly one of Q3 and Q5 is -H; and Q2, Q6, Q7 and Q8 are independently imidazo[1,2-a]pyridine substituents, such as -H, -F, -Cl, -Br, and -I.(FR) Cette invention concerne des analogues de nucléosides ayant une activité antivirale et une stabilité métabolique améliorées, des compositions contenant ces nucléosides et des méthodes de traitements antiviraux faisant appel à eux. Plus particulièrement, cette invention concerne des imidazo[1,2-a]pyridine C-nucléosides, comme par exemple des composés tels que les imidazo[1,2-a]pyridine C5-nucléosides et les imidazo[1,2-a]pyridine C3-nucléosides. Ces composés peuvent être représentés par la formule (I), où un seul des deux groupes Q3 et Q5 est une fraction du type sucre; un seul des deux groupes Q3 et Q5 est -H; et Q2, Q6, Q7 et Q8 sont, d'une manière indépendante, des substituants de imidazo[1,2-a]pyridine, comme par exemple -H, -F, Cl, -Br et -I.