9-chloro-4,5-dihydro-2-phenyl-6H-imidazo[4,5,1-ij]quinoline-6-one | 134602-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 9-chloro-4,5-dihydro-2-phenyl-6H-imidazo[4,5,1-ij]quinoline-6-one
• 英文别名: 5-Chloro-2-phenyl-1,3-diazatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-9-one
• CAS: 134602-39-4
• 化学式: C₁₆H₁₁ClN₂O
• 分子量: 282.729
• InChiKey: WLCVPSHSIGQMER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-chloro-4,5-dihydro-2-phenyl-6H-imidazo[4,5,1-ij]quinoline-6-one 在 吡啶 、 盐酸羟胺 、 三氧化硫吡啶 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 31.0h， 生成 (E)-9-chloro-4,5-dihydro-2-phenyl-6H-imidazo(4,5,1-ij)quinolin-6-one 6-oxime-O-sulfonic acid potassium salt
  参考文献：
  名称：

  Synthesis and diuretic activity of 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one6-oxime-O-sulfonic acid derivatives

  摘要：

  Using our previously reported 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 1a (M17055) as a lead, a series of tricyclic (2a-o, 3, 4, 5) and tetracyclic (6) quinolinone oxime O-sulfonic acid derivatives were synthesized by ring annulation of the 1-(2-methylbenzoyl) moiety to the quinolinone skeleton. They were compared with furosemide and compound la for diuretic activity in dogs; some tricyclic 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one 6-oxime-O-sulfonic acid derivatives showed diuretic activity comparable (2c,e) or superior (2m) to the lead compound la. These results are discussed on the basis of a comparison of the conformational and electronic characteristics of the relevant compounds with the aid of computer graphics. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80028-2
• 作为产物：
  描述：

  8-amino-7-chloro-2,3-dihydro-4(1H)-quinolinone 在 盐酸 、 苯甲醛 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 9-chloro-4,5-dihydro-2-phenyl-6H-imidazo[4,5,1-ij]quinoline-6-one
  参考文献：
  名称：

  4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one-6-oxime-O-sulfonic acid

  摘要：

  本发明涉及新颖的4,5-二氢-6H-咪唑[4,5,1-ij]喹啉-6-酮-6-肟-O-磺酸化合物，制备该化合物的方法，中间体化合物，即新颖的4,5-二氢-6H-咪唑[4,5,1-ij]喹啉-6-酮化合物和4,5-二氢-6H-咪唑[4,5,1-ij]喹啉-6-酮-6-肟化合物在合成该化合物时的作用，制备该中间体化合物的方法，以及含有该化合物的制药或兽药组合物。本发明基于在4,5-二氢-6H-咪唑[4,5,1-ij]-喹啉-6-酮-6-肟-O-磺酸化合物的2-位置选择取代基，即2-(2-戊烯-3-基)-、2-环己基-、2-萘基-、2-噻吩基等。含有这些取代基的本发明化合物具有强效的降压、抗水肿和利尿作用，以及去除腹水的活性。本发明的化合物对于治疗上述疾病和疾患非常有用。

  公开号：

  US05151431A1

文献信息

• 4,5-Dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one-6-oxime-O-sulfonic acid derivatives
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0405442A1

  公开（公告）日：1991-01-02

  The present invention relates to novel 4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one-6-oxime-0-sulfonic acid compounds, processes for producing said compounds, intermediate compounds, i.e. novel 4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one compounds and 4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one-6-oxime compounds in the synthesis of said compounds, processes for producing said intermediate compounds, and pharmaceutical or veterinary compositions containing said compounds. The present invention is based on the selection of the substituents of 4,5-dihydro-6H-imidazo[4,5,1-ij]-quinolin-6-one-6-oxime-O-sulfonic acid compounds at 2-position, namely 2-(2-penten-3-yl)-, 2-cyclohexyl-, 2-naphthyl-, 2-thienyl-, etc. The compounds of the present invention containing these substituents have potent- hypotensive, antioedematous and diuretic effects as well as an activity of removing ascites. The compounds of the present invention are extremely useful for treatment of diseases and disorders mentioned above.

  本发明涉及新型 4,5-二氢-6H-咪唑并[4,5,1-ij]喹啉-6-酮-6-肟-0-磺酸化合物、生产上述化合物的工艺、中间化合物，即新型 4,5-二氢-6H-咪唑并[4,5,1-ij]喹啉-6-酮化合物和合成所述化合物的 4,5-二氢-6H-咪唑并[4,5,1-ij]喹啉-6-酮-6-肟化合物，生产所述中间化合物的工艺，以及含有所述化合物的药物或兽药组合物。 本发明基于对 4,5-二氢-6H-咪唑并[4,5,1-ij]-喹啉-6-酮-6-肟-O-磺酸化合物 2-位取代基的选择，即 2-(2-戊烯-3-基)-、2-环己基-、2-萘基-、2-噻吩基-等。 含有这些取代基的本发明化合物具有强效降血压、消肿和利尿作用，并具有去除腹水的活性。本发明的化合物对治疗上述疾病和失调非常有用。
• US5151431A
  申请人：——

  公开号：US5151431A

  公开（公告）日：1992-09-29
• Synthesis and diuretic activity of 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one6-oxime-O-sulfonic acid derivatives
  作者：Kazumi Nishijima、Tomoaki Shinkawa、Manabu Ito、Hidemitsu Nishida、Ichirou Yamamoto、Yoshiaki Onuki、Hitoshi Inaba、Soutarou Miyano

  DOI：10.1016/s0223-5234(99)80028-2

  日期：1998.10

  Using our previously reported 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 1a (M17055) as a lead, a series of tricyclic (2a-o, 3, 4, 5) and tetracyclic (6) quinolinone oxime O-sulfonic acid derivatives were synthesized by ring annulation of the 1-(2-methylbenzoyl) moiety to the quinolinone skeleton. They were compared with furosemide and compound la for diuretic activity in dogs; some tricyclic 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one 6-oxime-O-sulfonic acid derivatives showed diuretic activity comparable (2c,e) or superior (2m) to the lead compound la. These results are discussed on the basis of a comparison of the conformational and electronic characteristics of the relevant compounds with the aid of computer graphics. (C) Elsevier, Paris.
• 4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one-6-oxime-O-sulfonic acid
  申请人：Mochida Pharmaceutical Co., Ltd.

  公开号：US05151431A1

  公开（公告）日：1992-09-29

  The present invention relates to novel 4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one-6-oxime-O-sulfonic acid compounds, processes for producing said compounds, intermediate compounds, i.e. novel 4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one compounds and 4,5-dihydro-6H-imidazo[4,5,1-ij]quinolin-6-one-6-oxime compounds in the synthesis of said compounds, processes for producing said intermediate compounds, and pharmaceutical or veterinary compositions containing said compounds. The present invention is based on the selection of the substituents of 4,5-dihydro-6H-imidazo[4,5,1-ij]-quinolin-6-one-6-oxime-O-sulfonic acid compounds at 2-position, namely 2-(2-penten-3-yl)-, 2-cyclohexyl-, 2-naphthyl-, 2-thienyl-, etc. The compounds of the present invention containing these substituents have potent hypotensive, anti-oedematous and diuretic effects as well as an activity of removing ascites. The compounds of the present invention are extremely useful for treatment of diseases and disorders mentioned above.

  本发明涉及新颖的4,5-二氢-6H-咪唑[4,5,1-ij]喹啉-6-酮-6-肟-O-磺酸化合物，制备该化合物的方法，中间体化合物，即新颖的4,5-二氢-6H-咪唑[4,5,1-ij]喹啉-6-酮化合物和4,5-二氢-6H-咪唑[4,5,1-ij]喹啉-6-酮-6-肟化合物在合成该化合物时的作用，制备该中间体化合物的方法，以及含有该化合物的制药或兽药组合物。本发明基于在4,5-二氢-6H-咪唑[4,5,1-ij]-喹啉-6-酮-6-肟-O-磺酸化合物的2-位置选择取代基，即2-(2-戊烯-3-基)-、2-环己基-、2-萘基-、2-噻吩基等。含有这些取代基的本发明化合物具有强效的降压、抗水肿和利尿作用，以及去除腹水的活性。本发明的化合物对于治疗上述疾病和疾患非常有用。