5-(4-chloro-6-methoxy-3-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)-3,4-di(phenylcarbonyloxy)-2-phenylcarbonyloxymethyl-(2R,3R,4R,5R)-tetrahydrofuran | 175543-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-chloro-6-methoxy-3-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)-3,4-di(phenylcarbonyloxy)-2-phenylcarbonyloxymethyl-(2R,3R,4R,5R)-tetrahydrofuran
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4-chloro-6-methoxy-3-methylpyrazolo[3,4-b]quinolin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 175543-57-4
• 化学式: C₃₈H₃₀ClN₃O₈
• 分子量: 692.124
• InChiKey: XAEVIUOLWCMPKA-RWGWTQFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-(4-chloro-6-methoxy-3-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)-3,4-di(phenylcarbonyloxy)-2-phenylcarbonyloxymethyl-(2R,3R,4R,5R)-tetrahydrofuran 在 甲醇 、 sodium periodate 、 (NH₄)4B₂O₇ 、 氨 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 生成 1-[(2R,6S)-4-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-morpholin-2-yl]-4-chloro-6-methoxy-3-methyl-1H-pyrazolo[3,4-b]quinoline
  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：

  (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-6-methoxy-3-methyl-2H-pyrazolo[3,4-b]quinolin-2-yl)tetrahydrofuran-3,4-diyl dibenzoate 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 5-(4-chloro-6-methoxy-3-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)-3,4-di(phenylcarbonyloxy)-2-phenylcarbonyloxymethyl-(2R,3R,4R,5R)-tetrahydrofuran
  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

文献信息

• Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras
  作者：Ronald Wolin、David Wang、Joseph Kelly、Adriano Afonso、Linda James、Paul Kirschmeier、Andrew T McPhail

  DOI：10.1016/0960-894x(95)00574-d

  日期：1996.1

  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)