5-[(dimethylamino)methylidene]-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-one | 225782-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[(dimethylamino)methylidene]-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-one
• 英文别名: 5-Dimethylaminomethylene-1,5,6,7-tetrahydro-(1-phenyl)-4H-indazol-4-one；5-(Dimethylaminomethylidene)-1-phenyl-6,7-dihydroindazol-4-one
• CAS: 225782-22-9
• 化学式: C₁₆H₁₇N₃O
• 分子量: 267.33
• InChiKey: HOBUTOFXYFZVHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(dimethylamino)methylidene]-1-phenyl-1,5,6,7-tetrahydro-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 126.0h， 生成 2-Oxo-7-phenyl-2,7-dihydro-pyrano[2,3-e]indazole-3-carboxylic acid methyl 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-苯基-6,7-二氢-1H-吲唑-4(5H)-酮 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到5-[(dimethylamino)methylidene]-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-one
  参考文献：
  名称：

  Pyrazolo[3,4-h]quinolines promising photosensitizing agents in the treatment of cancer

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.08.003

文献信息

• [EN] SUBSTITUTED PYRAZOLO [3, 4-B] PYRIDINE COMPOUNDS<br/>[FR] COMPOSÉS DE PYRAZOLO[3,4-B]PYRIDINE SUBSTITUÉS
  申请人：ARQULE INC

  公开号：WO2010078427A1

  公开（公告）日：2010-07-08

  The present invention relates to substituted imidazoly 1-5,6- dihydrobenzo[n]isoquinoline compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted imidazolyl-5,6-dihydrobenzo[n]isoquinoline compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及替代咪唑基-5,6-二氢苯并[ｎ]异喹啉化合物及合成这些化合物的方法。本发明还涉及含有替代咪唑基-5,6-二氢苯并[ｎ]异喹啉化合物的药物组合物，以及通过向需要的受试者投予这些化合物和药物组合物来治疗细胞增殖性疾病，如癌症的方法。
• SUBSTITUTED IMIDAZOLYL-5,6-DIHYDROBENZO[N]ISOQUINOLINE COMPOUNDS
  申请人：Ali Syed M.

  公开号：US20100239526A1

  公开（公告）日：2010-09-23

  The present invention relates to substituted imidazolyl-5,6-dihydrobenzo[n]isoquinoline compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted imidazolyl-5,6-dihydrobenzo[n]isoquinoline compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及取代的咪唑基-5,6-二氢苯并[n]异喹啉化合物及其合成方法。本发明还涉及含有取代的咪唑基-5,6-二氢苯并[n]异喹啉化合物的制药组合物，以及通过向需要治疗细胞增殖性疾病（如癌症）的受试者施用这些化合物和制药组合物来治疗的方法。
• SUBSTITUTED PYRAZOLO [3, 4-B]PYRIDINE COMPOUNDS
  申请人：ArQule, Inc.

  公开号：EP2379551A1

  公开（公告）日：2011-10-26
• US8263610B2
  申请人：——

  公开号：US8263610B2

  公开（公告）日：2012-09-11