6-chloro-1-(2,4-dichlorobenzoyl)-2,3-dihydro-4(1H)-quinolinone | 114417-15-1

• 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: 6-chloro-1-(2,4-dichlorobenzoyl)-2,3-dihydro-4(1H)-quinolinone
• 英文别名: 6-chloro-1-(2,4-dichlorobenzoyl)-2,3-dihydroquinolin-4-one
• CAS: 114417-15-1
• 化学式: C₁₆H₁₀Cl₃NO₂
• 分子量: 354.62
• InChiKey: UTVCKTZJFYUJHR-UHFFFAOYSA-N

物化性质

• 熔点：
  176.8-177.8 °C
• 沸点：
  535.5±50.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-1-(2,4-dichlorobenzoyl)-2,3-dihydro-4(1H)-quinolinone 在 potassium carbonate 、 hydroxylamine-O-sulfonic acid 作用下， 生成 potassium;[(E)-[6-chloro-1-(2,4-dichlorobenzoyl)-2,3-dihydroquinolin-4-ylidene]amino] sulfate
  参考文献：
  名称：

  Synthesis and diuretic activity of 2,3-dihydro-4(1H)-quinolinone 4-oxime-O-sulfonic acid derivatives

  摘要：

  The diuretic activity of 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime 1 (M12285) was previously shown to derive from a 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime-O-sulfonic acid salt as a rat metabolite. Thus, in the present study, the potassium salt 2 (M17000) was synthesized to unambiguously establish the structure as well as the stereochemistry of the oxime. The structural features of compounds 1 and 2 were compared with those of conventional diuretics by electrostatic potential maps. Using compound 2 as a lead compound, various quinolinone oxime sulfonic acid derivatives were synthesized and the diuretic activity for elucidation of the structure-activity relationships examined. Among the compounds synthesized, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 3 (M17055) showed a particularly high activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80061-5
• 作为产物：
  描述：

  6-氯-2,3-二氢喹啉-4-酮 、 2,4-二氯苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 6-chloro-1-(2,4-dichlorobenzoyl)-2,3-dihydro-4(1H)-quinolinone
  参考文献：
  名称：

  Synthesis and diuretic activity of 2,3-dihydro-4(1H)-quinolinone 4-oxime-O-sulfonic acid derivatives

  摘要：

  The diuretic activity of 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime 1 (M12285) was previously shown to derive from a 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime-O-sulfonic acid salt as a rat metabolite. Thus, in the present study, the potassium salt 2 (M17000) was synthesized to unambiguously establish the structure as well as the stereochemistry of the oxime. The structural features of compounds 1 and 2 were compared with those of conventional diuretics by electrostatic potential maps. Using compound 2 as a lead compound, various quinolinone oxime sulfonic acid derivatives were synthesized and the diuretic activity for elucidation of the structure-activity relationships examined. Among the compounds synthesized, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 3 (M17055) showed a particularly high activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80061-5

文献信息

• 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives
  申请人：Mochida Pharmaceutical Co., Ltd.

  公开号：US04839368A1

  公开（公告）日：1989-06-13

  The present invention relates to novel 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, processes for producing said derivatives, intermediate compounds to produce said derivatives, processes to produce said intermediate compounds, and compositions containing said derivatives with potent diuretic activity that can be used for treating and/or preventing hypertension, oedema and/or for removing ascites. The present invention is based on the selection of 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, namely O-sulfate, O-mesylate, O-methylphosphate and O-carboxymethyl ether, especially O-sulfate of 4-oxime. The compounds of the present invention containing these substituents have potent hypotensive, anti-oedematous and diuretic effect as well as an activity to remove ascites and are extremely useful for the treatment of diseases and disorders mentioned above.

  本发明涉及新型1-酰基-2,3-二氢-4(1H)-喹啉酮-4-羟肟衍生物，生产该衍生物的方法，用于生产该衍生物的中间化合物，生产该中间化合物的方法，以及含有具有强效利尿活性的该衍生物的组合物，可用于治疗和/或预防高血压、水肿以及去除腹水。本发明基于选择1-酰基-2,3-二氢-4(1H)-喹啉酮-4-羟肟衍生物，即O-硫酸酯、O-甲磺酸酯、O-甲基磷酸酯和O-羧甲基醚，特别是4-羟肟的O-硫酸酯。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，对于治疗上述疾病和紊乱非常有用。
• Intermediate compounds of 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime
  申请人：Mochida Pharmaceutical Co., Ltd.

  公开号：US05077410A1

  公开（公告）日：1991-12-31

  The present invention relates to intermediate compounds to produce novel 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives with potent diuretic activity that can be used for treating and/or preventing hypertension, oedema and/or for removing ascites. The present invention is based on two characters. One is the selection of acyl substituents of 2,3-dihydro-4(1H)-quinolinone at 1-position, namely propionyl, t-butylcarbonyl, benzoyl, 2-bromobenzoyl, 4-chlorobenzoyl, 2-methylbenzoyl, 2-ethylbenzoyl, 2,3-dimethoxybenzoyl, 2,4-dichlorobenzoyl, 4-chloro-2-methyl benzoyl or 2-chloro-4-nitrobenzoyl. The other is the selection of substituents and positional specificity at 6- or 7-position, namely halogen atom, methoxy, trifluoromethyl or dimethylamino group. 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives which are made from the intermediate compounds of the present invention have potent hypotensive, antioedematous and diuretic effect as well as an activity to remove ascites, and are extremely useful for the treatment of diseases and disorders mentioned above.

  本发明涉及中间化合物，用于生产具有强效利尿作用的新型1-酰基-2,3-二氢-4（1H）-喹啉酮-4-肟衍生物，可用于治疗和/或预防高血压、水肿和/或去除腹水。本发明基于两个特点。一个是选择2,3-二氢-4（1H）-喹啉酮在1位的酰基取代基，即丙酰基、叔丁基羰基、苯甲酰基、2-溴苯甲酰基、4-氯苯甲酰基、2-甲基苯甲酰基、2-乙基苯甲酰基、2,3-二甲氧基苯甲酰基、2,4-二氯苯甲酰基、4-氯-2-甲基苯甲酰基或2-氯-4-硝基苯甲酰基。另一个是在6-或7-位选择取代基和位置特异性，即卤原子、甲氧基、三氟甲基或二甲基氨基。由本发明的中间化合物制备的1-酰基-2,3-二氢-4（1H）-喹啉酮-4-肟衍生物具有强效降压、抗水肿和利尿作用，以及去除腹水的活性，极其有用于治疗上述疾病和疾患。
• 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivative, process for the production thereof, pharmaceutical composition and intermediates
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0243982B1

  公开（公告）日：1991-04-17
• US4839368A
  申请人：——

  公开号：US4839368A

  公开（公告）日：1989-06-13
• US5077410A
  申请人：——

  公开号：US5077410A

  公开（公告）日：1991-12-31