(2R,3R,4S,5R)-2-(4-Chloro-6-methoxy-3-methyl-pyrazolo[3,4-b]quinolin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol | 175543-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,3R,4S,5R)-2-(4-Chloro-6-methoxy-3-methyl-pyrazolo[3,4-b]quinolin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
• CAS: 175543-48-3
• 化学式: C₁₇H₁₈ClN₃O₅
• 分子量: 379.8
• InChiKey: AALCTZNPKCKPAU-BNGXUDDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  109.86
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-2-(4-Chloro-6-methoxy-3-methyl-pyrazolo[3,4-b]quinolin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol 在 盐酸 、 对甲苯磺酸 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-[(2R,3S,4R,5R)-5-(4-Chloro-6-methoxy-3-methyl-pyrazolo[3,4-b]quinolin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-3-hydroxy-1-phenyl-propan-1-one
  参考文献：
  名称：

  Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras

  摘要：

  A series of pyrazolo[3,4-b]quinoline ribofuranosides were prepared using the glycosylation methodology of Vorbruggen. Oxidative cleavage of the ribose moiety in 6 furnished the dialdehyde intermediate 36, which cyclizes upon reductive amination providing the morpholino compound 37. Derivatives from both the ribose and morpholino series were evaluated for their ability to inhibit the nucleotide exchange process of oncogenic Ras.(1a)

  DOI：

  10.1016/0960-894x(95)00574-d
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 氨 、 三甲基硅烷基二乙胺 作用下， 反应 74.0h， 生成 (2R,3R,4S,5R)-2-(4-Chloro-6-methoxy-3-methyl-pyrazolo[3,4-b]quinolin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras

  摘要：

  A series of pyrazolo[3,4-b]quinoline ribofuranosides were prepared using the glycosylation methodology of Vorbruggen. Oxidative cleavage of the ribose moiety in 6 furnished the dialdehyde intermediate 36, which cyclizes upon reductive amination providing the morpholino compound 37. Derivatives from both the ribose and morpholino series were evaluated for their ability to inhibit the nucleotide exchange process of oncogenic Ras.(1a)

  DOI：

  10.1016/0960-894x(95)00574-d