N-(3,4-Dihydro-1H-2-oxa-4,12-diaza-benzo[a]anthracen-10-yl)-methanesulfonamide | 208656-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(3,4-Dihydro-1H-2-oxa-4,12-diaza-benzo[a]anthracen-10-yl)-methanesulfonamide
• 英文别名: N-(3,4-dihydro-1H-[1,3]oxazino[4,5-c]acridin-10-yl)methanesulfonamide
• CAS: 208656-31-9
• 化学式: C₁₆H₁₅N₃O₃S
• 分子量: 329.379
• InChiKey: IBHBQNQYGLOBPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3,4-Dihydro-1H-2-oxa-4,12-diaza-benzo[a]anthracen-10-yl)-methanesulfonamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-(5-Hydroxymethyl-6-methylamino-acridin-3-yl)-N-methyl-methanesulfonamide
  参考文献：
  名称：

  4-Hydroxymethyl-3-aminoacridine Derivatives as a New Family of Anticancer Agents

  摘要：

  3-Amino- and 3-alkylamino-4-hydroxymethylacridines bearing various substituents on the C ring have been prepared by regioselective electrophilic aromatic substitution of the corresponding 3-aminoacridines and ring opening of the dihydrooxazinoacridine key intermediates. Most of the new compounds show potent cytotoxic activities against murine L1210 (leukemia), human A549 (lung), and HT29 (colon) cancer cell lines. The most cytotoxic molecules, 1 and 13, are active at nanomolar concentrations. As predicted for acridine derivatives, the new compounds intercalate in DNA, but interestingly they do not interfere with topoisomerase I and II activities. The mode of action remains uncertain because intracellular distribution indicated very different behaviors for 1 and 13. Compound 13 is uniformly distributed in the cell both in the cytoplasm and in the nucleus, whereas compound 1 is essentially localized in cytoplasmic granules.

  DOI：

  10.1021/jm020389w
• 作为产物：
  描述：

  3,4-dihydro-10-(N,N-bismethanesulfonylamino)-1H-[1,3]-oxazino[4,5-c]acridine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(3,4-Dihydro-1H-2-oxa-4,12-diaza-benzo[a]anthracen-10-yl)-methanesulfonamide
  参考文献：
  名称：

  4-Hydroxymethyl-3-aminoacridine Derivatives as a New Family of Anticancer Agents

  摘要：

  3-Amino- and 3-alkylamino-4-hydroxymethylacridines bearing various substituents on the C ring have been prepared by regioselective electrophilic aromatic substitution of the corresponding 3-aminoacridines and ring opening of the dihydrooxazinoacridine key intermediates. Most of the new compounds show potent cytotoxic activities against murine L1210 (leukemia), human A549 (lung), and HT29 (colon) cancer cell lines. The most cytotoxic molecules, 1 and 13, are active at nanomolar concentrations. As predicted for acridine derivatives, the new compounds intercalate in DNA, but interestingly they do not interfere with topoisomerase I and II activities. The mode of action remains uncertain because intracellular distribution indicated very different behaviors for 1 and 13. Compound 13 is uniformly distributed in the cell both in the cytoplasm and in the nucleus, whereas compound 1 is essentially localized in cytoplasmic granules.

  DOI：

  10.1021/jm020389w

文献信息

• Reaction of Proflavine Derivatives with Formaldehyde: Access to Mono- and Bis-(3,4-dihydro[1,3]oxazino)acridines of Pharmacological Interest
  作者：Martine Demeunynck、Noémie Fixler Fixler、Alain Duflos、Jean Lhomme

  DOI：10.3987/com-97-8083

  日期：——
• 4-Hydroxymethyl-3-aminoacridine Derivatives as a New Family of Anticancer Agents
  作者：Franck Charmantray、Martine Demeunynck、Danièle Carrez、Alain Croisy、Amélie Lansiaux、Christian Bailly、Pierre Colson

  DOI：10.1021/jm020389w

  日期：2003.3.1

  3-Amino- and 3-alkylamino-4-hydroxymethylacridines bearing various substituents on the C ring have been prepared by regioselective electrophilic aromatic substitution of the corresponding 3-aminoacridines and ring opening of the dihydrooxazinoacridine key intermediates. Most of the new compounds show potent cytotoxic activities against murine L1210 (leukemia), human A549 (lung), and HT29 (colon) cancer cell lines. The most cytotoxic molecules, 1 and 13, are active at nanomolar concentrations. As predicted for acridine derivatives, the new compounds intercalate in DNA, but interestingly they do not interfere with topoisomerase I and II activities. The mode of action remains uncertain because intracellular distribution indicated very different behaviors for 1 and 13. Compound 13 is uniformly distributed in the cell both in the cytoplasm and in the nucleus, whereas compound 1 is essentially localized in cytoplasmic granules.