2,6,7-Trichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6,7-Trichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine
• 英文别名: (2R,3S,4R,5S)-2-(hydroxymethyl)-5-(2,6,7-trichloroimidazo[1,2-a]pyridin-5-yl)tetrahydrofuran-3,4-diol；(2R,3S,4R,5S)-2-(hydroxymethyl)-5-(2,6,7-trichloroimidazo[1,2-a]pyridin-5-yl)oxolane-3,4-diol
• 化学式: C₁₂H₁₁Cl₃N₂O₄
• 分子量: 353.589
• InChiKey: LETVLOJWSLRUFP-DSXAJKCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 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：
  87.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6,7-trichloro-5-[5-O-(tert-butyldimethylsilyl)-1-acetoxy-2,3-O-isopropylidene-α-D-ribofuranosyl]imidazo[1,2-a]pyridine 在 盐酸 、 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2,6,7-Trichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis of Imidazo[1,2-a]pyridine C-Nucleosides with an Unexpected Site of Ribosylation

  摘要：

  Several new polychlorinated imidazo[1,2-alpha]pyridine C-nucleosides have been prepared. Lithiated imidazo[1,2-alpha]pyridines were condensed with protected ribonolactones, trapped as 1'-acetoxy derivatives, and these 1'-acetoxy derivatives were reductively deacetoxylated and deprotected to give C-nucleosides. Long-range proton-carbon decoupling experiments were used to determine the actual site of ribosylation and established that the ribose moiety was unexpectedly attached to the C5 position of the imidazo[1,2-alpha]pyridines. This method has provided C-nucleosides, such as 2,6-dichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and 2,6,7-trichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and the corresponding alpha-products.

  DOI：

  10.1021/jo9619342

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.
• Synthesis of Imidazo[1,2-<i>a</i>]pyridine C-Nucleosides with an Unexpected Site of Ribosylation
  作者：Kristjan S. Gudmundsson、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jo9619342

  日期：1997.5.1

  Several new polychlorinated imidazo[1,2-alpha]pyridine C-nucleosides have been prepared. Lithiated imidazo[1,2-alpha]pyridines were condensed with protected ribonolactones, trapped as 1'-acetoxy derivatives, and these 1'-acetoxy derivatives were reductively deacetoxylated and deprotected to give C-nucleosides. Long-range proton-carbon decoupling experiments were used to determine the actual site of ribosylation and established that the ribose moiety was unexpectedly attached to the C5 position of the imidazo[1,2-alpha]pyridines. This method has provided C-nucleosides, such as 2,6-dichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and 2,6,7-trichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and the corresponding alpha-products.