5-Dimethylaminomethylene-1,5,6,7-tetrahydro-(1-methyl)-4H-indazol-4-one | 225782-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Dimethylaminomethylene-1,5,6,7-tetrahydro-(1-methyl)-4H-indazol-4-one
• 英文别名: 5-[(dimethylamino)methylidene]-1-methyl-1,5,6,7-tetrahydro-4H-indazol-4-one；5-(dimethylaminomethylidene)-1-methyl-6,7-dihydroindazol-4-one
• CAS: 225782-21-8
• 化学式: C₁₁H₁₅N₃O
• 分子量: 205.26
• InChiKey: PXXKHPRFFRDLBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.13
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Dimethylaminomethylene-1,5,6,7-tetrahydro-(1-methyl)-4H-indazol-4-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 30.0h， 生成 7-Methyl-2-oxo-2,7-dihydro-pyrano[2,3-e]indazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of angelicin heteroanalogues: preliminary photobiological and pharmacological studies

  摘要：

  A series of angelicin heteroanalogues, in which the furan was replaced by thiophene or a 1-substituted pyrazole moiety, was synthesised in order to obtain potential therapeutic agents with antiproliferative and/or other biological activities. In general, the antiproliferative activity of the new thioangelicin, tested in different biological substrates, appeared to be higher than that of the angelicin, the natural parent compound, but lower than that of 8-MOP, the furocoumarin ordinarily used in PUVA therapy and photopheresis. Thioangelicin 6 induced strong inhibition of T2 bacteriophage infectivity and was able to significantly repress the DNA. synthesis in Ehrlich ascites cells and the clonal growth in HeLa cells. The pyrazolocoumarins did not show any noticeable effect upon UVA irradiation in all the biological systems considered. All the new angelicin heteroanalogues appeared to be free of the known phototoxicity of furocoumarins on the skin. The pyrazolocoumarins have also been tested as anti-inflammatory, analgesic, antipyretic, local anaesthetic, anti-arrhythmic and platelet antiaggregating agents by standard procedures. In this class of derivatives, 10a showed good anti-inflammatory and antipyretic properties, while 9a and 11a showed significant local anaesthetic activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00076-7
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 1-Methyl-6,7-dihydro-1H-indazole-4,5-dione 反应 24.0h， 以40%的产率得到5-Dimethylaminomethylene-1,5,6,7-tetrahydro-(1-methyl)-4H-indazol-4-one
  参考文献：
  名称：

  Synthesis of angelicin heteroanalogues: preliminary photobiological and pharmacological studies

  摘要：

  A series of angelicin heteroanalogues, in which the furan was replaced by thiophene or a 1-substituted pyrazole moiety, was synthesised in order to obtain potential therapeutic agents with antiproliferative and/or other biological activities. In general, the antiproliferative activity of the new thioangelicin, tested in different biological substrates, appeared to be higher than that of the angelicin, the natural parent compound, but lower than that of 8-MOP, the furocoumarin ordinarily used in PUVA therapy and photopheresis. Thioangelicin 6 induced strong inhibition of T2 bacteriophage infectivity and was able to significantly repress the DNA. synthesis in Ehrlich ascites cells and the clonal growth in HeLa cells. The pyrazolocoumarins did not show any noticeable effect upon UVA irradiation in all the biological systems considered. All the new angelicin heteroanalogues appeared to be free of the known phototoxicity of furocoumarins on the skin. The pyrazolocoumarins have also been tested as anti-inflammatory, analgesic, antipyretic, local anaesthetic, anti-arrhythmic and platelet antiaggregating agents by standard procedures. In this class of derivatives, 10a showed good anti-inflammatory and antipyretic properties, while 9a and 11a showed significant local anaesthetic activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00076-7

文献信息

• Pyrazolo[3,4-h]quinolines promising photosensitizing agents in the treatment of cancer
  作者：Virginia Spanò、Barbara Parrino、Anna Carbone、Alessandra Montalbano、Alessia Salvador、Paola Brun、Daniela Vedaldi、Patrizia Diana、Girolamo Cirrincione、Paola Barraja

  DOI：10.1016/j.ejmech.2015.08.003

  日期：2015.9

  A new series of pyrazolo[3,4-h]quinolines, heteroanalogues of angelicin was conveniently prepared with a broad substitution pattern. A large number of derivatives was obtained and the cellular photocytotoxicity was evaluated in vitro against 5 different human tumor cell lines with GI(50) values reaching the nanomolar level (14.52-0.04 mu M). Selected compounds were able to photoinduce a massive cell death with the involvement of mitochondria. Their photodamage cellular targets were proteins and lipids and they did not cause any kind of DNA photodamage. This latter event is of considerable importance in the modulation of long term side effects, generally associated with the use of classical furocoumarins. (C) 2015 Elsevier Masson SAS. All rights reserved.