1-(5-Methoxy-1-phenylsulphonylindol-2-yl)-1-methylfuro<3,4-c>pyridin-3(1H)-one | 139260-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(5-Methoxy-1-phenylsulphonylindol-2-yl)-1-methylfuro<3,4-c>pyridin-3(1H)-one
• 英文别名: 1-[1-(Benzenesulfonyl)-5-methoxyindol-2-yl]-1-methylfuro[3,4-c]pyridin-3-one
• CAS: 139260-65-4
• 化学式: C₂₃H₁₈N₂O₅S
• 分子量: 434.472
• InChiKey: YIXAFEAZTZTUOY-UHFFFAOYSA-N

物化性质

• 沸点：
  692.5±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-Methoxy-1-phenylsulphonylindol-2-yl)-1-methylfuro<3,4-c>pyridin-3(1H)-one 在 甲酸 、 N,N'-羰基二咪唑 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 N-<3-(Dimethylamino)propyl>-4-<1-(5-methoxy-1-phenylsulphonylindol-2-yl)ethyl>nicotinamide
  参考文献：
  名称：

  Synthesis of 11-amino-substituted-9-methoxy-5-methyl-6H-pyrido[4,3-b]-carbazoles

  摘要：

  A route to 11-amino-substituted-6H-pyrido[4,3-b]carbazoles has been studied. Thus, condensation of 2-(4-lithiopyridine-3-yl)-4,4-dimethyloxazoline with 2-acetyl-5-methoxy-1-phenylsulphonylindole led to a low yield of the expected alcohol, which upon hydrolysis gave a complex mixture. A better starting building block was 4-acetyl-N,N-diisopropylnicotinamide obtained either from N,N-diisopropyl-4-lithionicotinamide (low yield) or from pyridine-3,4-dicarboxylic anhydride, using a 4-step sequence. This compound was treated with 2-lithio-5-methoxy-1-phenylsulphonylindole, affording N,N-diisopropyl-4-[1-(5-methoxy-1-phenylsulphonylindol-2-yl)-1-hydroxyethyl]nicotinamide. Hydrolysis and then reduction led to 4-[1-(5-methoxy-1-phenylsulphonylindol-2-yl)-ethyl]nicotinic acid whose amides were cyclized by phosphorus trichlorideoxide. Finally, the title compounds were obtained by Raney-nickel reduction-elimination of the 6-phenylsulphonyl protecting group.

  DOI：

  10.1039/p19910003165
• 作为产物：
  描述：

  1-(苯磺酰基)-5-甲氧基吲哚 在 正丁基锂 、 硫酸 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 25.5h， 生成 1-(5-Methoxy-1-phenylsulphonylindol-2-yl)-1-methylfuro<3,4-c>pyridin-3(1H)-one
  参考文献：
  名称：

  N-Methylcarbamate derivatives of ellipticine and olivacine with cytotoxic activity against four human lung cancer cell lines

  摘要：

  A series of analogues of the antitumor alkaloids ellipticine and olivacine were tested for cytotoxicity against four human lung cancer cell lines: H69, N417, H460, and H358. Adriamycin (doxorubicin), ellipticine, olivacine, and celiptinium were used as standards. Adriamycin was cytotoxic at 2 muM and celiptinium was inactive at the highest concentrations tested (IC50 > 48 muM). N-methylcarbamates of 9-methoxy-6H-pyrido[4,3-b] carbazole 1-, 5-, and 11-methanols gave IC50 values ranging from 0.02 to 0.11 muM against N417, H460, and H358 and were only slightly less effective against H69.

  DOI：

  10.1021/jm00104a011

文献信息

• N-Methylcarbamate derivatives of ellipticine and olivacine with cytotoxic activity against four human lung cancer cell lines
  作者：John C. Ruckdeschel、Sandeep P. Modi、Wageeh El-Hamouly、Enrico Portuese、Sydney Archer

  DOI：10.1021/jm00104a011

  日期：1992.12

  A series of analogues of the antitumor alkaloids ellipticine and olivacine were tested for cytotoxicity against four human lung cancer cell lines: H69, N417, H460, and H358. Adriamycin (doxorubicin), ellipticine, olivacine, and celiptinium were used as standards. Adriamycin was cytotoxic at 2 muM and celiptinium was inactive at the highest concentrations tested (IC50 > 48 muM). N-methylcarbamates of 9-methoxy-6H-pyrido[4,3-b] carbazole 1-, 5-, and 11-methanols gave IC50 values ranging from 0.02 to 0.11 muM against N417, H460, and H358 and were only slightly less effective against H69.
• Synthesis of 11-amino-substituted-9-methoxy-5-methyl-6H-pyrido[4,3-b]-carbazoles
  作者：Isbelle Praly-Deprez、Christian Rivalle、Christiane Huel、Jean Belehradek、Claude Paoletti、Emile Bisagni

  DOI：10.1039/p19910003165

  日期：——

  A route to 11-amino-substituted-6H-pyrido[4,3-b]carbazoles has been studied. Thus, condensation of 2-(4-lithiopyridine-3-yl)-4,4-dimethyloxazoline with 2-acetyl-5-methoxy-1-phenylsulphonylindole led to a low yield of the expected alcohol, which upon hydrolysis gave a complex mixture. A better starting building block was 4-acetyl-N,N-diisopropylnicotinamide obtained either from N,N-diisopropyl-4-lithionicotinamide (low yield) or from pyridine-3,4-dicarboxylic anhydride, using a 4-step sequence. This compound was treated with 2-lithio-5-methoxy-1-phenylsulphonylindole, affording N,N-diisopropyl-4-[1-(5-methoxy-1-phenylsulphonylindol-2-yl)-1-hydroxyethyl]nicotinamide. Hydrolysis and then reduction led to 4-[1-(5-methoxy-1-phenylsulphonylindol-2-yl)-ethyl]nicotinic acid whose amides were cyclized by phosphorus trichlorideoxide. Finally, the title compounds were obtained by Raney-nickel reduction-elimination of the 6-phenylsulphonyl protecting group.