6,10-dimethyl-1,4-bis(methoxycarbonyl)pyridazino[4,5-h]psoralen | 615535-94-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,10-dimethyl-1,4-bis(methoxycarbonyl)pyridazino[4,5-h]psoralen
• 英文别名: Dimethyl 2,7-dimethyl-5-oxo-4,17-dioxa-13,14-diazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),2,6,8,11(16),12,14-heptaene-12,15-dicarboxylate；dimethyl 2,7-dimethyl-5-oxo-4,17-dioxa-13,14-diazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),2,6,8,11(16),12,14-heptaene-12,15-dicarboxylate
• CAS: 615535-94-9
• 化学式: C₁₉H₁₄N₂O₇
• 分子量: 382.329
• InChiKey: PMOKJAVKDFEUPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  280-282 °C(Solvent: 1,4-Dioxane)
• 沸点：
  645.6±55.0 °C(predicted)
• 密度：
  1.444±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6,10-dimethyl-1,4-bis(methoxycarbonyl)pyridazino[4,5-h]psoralen 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以75%的产率得到4,11-dimethylpyridazino[4,5-h]psoralen
  参考文献：
  名称：

  Pyridazinopsoralens of wide chemotherapeutic interest

  摘要：

  The synthesis of new 6,10-dimethylpyridazino[4,5-h] psoralens, carrying no (4), one (5), or two (6-9) dialkylaminoalkylcarboxamide side chains on the pyridazine ring is reported. All compounds exert a significant photoantiproliferative activity. Moreover, the derivatives characterised by the protonable side chains show a notable cytotoxicity in the dark. The investigation on the mechanism of action demonstrated the capacity to intercalate into DNA base pairs and to inhibit the relaxation activity of topoisomerase II. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.006
• 作为产物：
  描述：

  7-羟基-4,8-二甲基香豆素 在 4-二甲氨基吡啶 、 三氯化铝 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 6,10-dimethyl-1,4-bis(methoxycarbonyl)pyridazino[4,5-h]psoralen
  参考文献：
  名称：

  Synthesis and convenient functionalisation of pyridazinofurocoumarins: nitrogenated isosters of potent DNA inhibitors

  摘要：

  Pyridazino[3,4-h]psoralens and pyridazino[3,4-j]angelicins are prepared in good yield from resorcinols through a direct, easy and generally applicable synthetic route. The key step in this route is the inverse electron-demand Diels-Alder reaction between linear or angular furocoumarins and 3,6-bis(methoxycarbonyl)-1,2,4,5-tetrazine to give the dicarboxymethylated tetracycles. The ester group in the peri position with respect to the oxygen in the furan ring can be regioselectively transformed to give primary or secondary amides. Similarly, the two ester groups in the tetracycle can be transformed in a high-efficiency process to give bis-amides that can be either symmetrical (from the same amine) or unsymmetrical (from two different amines). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.051

文献信息

• Synthesis and convenient functionalisation of pyridazinofurocoumarins: nitrogenated isosters of potent DNA inhibitors
  作者：José Carlos González-Gómez、Lourdes Santana、Eugenio Uriarte

  DOI：10.1016/j.tet.2003.08.051

  日期：2003.10

  Pyridazino[3,4-h]psoralens and pyridazino[3,4-j]angelicins are prepared in good yield from resorcinols through a direct, easy and generally applicable synthetic route. The key step in this route is the inverse electron-demand Diels-Alder reaction between linear or angular furocoumarins and 3,6-bis(methoxycarbonyl)-1,2,4,5-tetrazine to give the dicarboxymethylated tetracycles. The ester group in the peri position with respect to the oxygen in the furan ring can be regioselectively transformed to give primary or secondary amides. Similarly, the two ester groups in the tetracycle can be transformed in a high-efficiency process to give bis-amides that can be either symmetrical (from the same amine) or unsymmetrical (from two different amines). (C) 2003 Elsevier Ltd. All rights reserved.
• Pyridazinopsoralens of wide chemotherapeutic interest
  作者：Lisa Dalla Via、Ornella Gia、Sebastiano Marciani Magno、Alessandra Braga、José Carlos González-Gómez、Lázaro Guillermo Pérez-Montoto、Eugenio Uriarte

  DOI：10.1016/j.bmc.2010.06.006

  日期：2010.8

  The synthesis of new 6,10-dimethylpyridazino[4,5-h] psoralens, carrying no (4), one (5), or two (6-9) dialkylaminoalkylcarboxamide side chains on the pyridazine ring is reported. All compounds exert a significant photoantiproliferative activity. Moreover, the derivatives characterised by the protonable side chains show a notable cytotoxicity in the dark. The investigation on the mechanism of action demonstrated the capacity to intercalate into DNA base pairs and to inhibit the relaxation activity of topoisomerase II. (C) 2010 Elsevier Ltd. All rights reserved.