7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt | 114417-20-8

• 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: 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt
• 英文别名: M17055；Alilusem potassium；potassium;[(E)-[7-chloro-1-(2-methylbenzoyl)-2,3-dihydroquinolin-4-ylidene]amino] sulfate
• CAS: 114417-20-8
• 化学式: C₁₇H₁₄ClN₂O₅S*K
• 分子量: 432.926
• InChiKey: NQFKOWCYLQFLSM-QTCZRQAZSA-M

物化性质

• 熔点：
  189 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-chloro-2,3-dihydro-1-(2-methyl-benzoyl)-4(1H)-quinolinone 在 potassium carbonate 、 hydroxylamine-O-sulfonic acid 作用下， 生成 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt
  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

• Synthesis and diuretic activity of 2,3-dihydro-4(1H)-quinolinone 4-oxime-O-sulfonic acid derivatives
  作者：Kazumi Nishijima、Tomoaki Shinkawa、Yoshiaki Yamashita、Naofumi Sato、Hidemitsu Nishida、Kazuo Kato、Yoshiaki Onuki、Masahiro Mizota、Kikuo Ohtomo、Soutarou Miyano

  DOI：10.1016/s0223-5234(98)80061-5

  日期：1998.4

  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.