3-<2-(3-hydroxyphenyl)-2-oxoethyl>-1-methyl-1H-imidazolium 4-methylbenzenesulfonate | 103793-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-<2-(3-hydroxyphenyl)-2-oxoethyl>-1-methyl-1H-imidazolium 4-methylbenzenesulfonate
• 英文别名: 1-(3-Hydroxyphenyl)-2-(3-methylimidazol-3-ium-1-yl)ethanone;4-methylbenzenesulfonate
• CAS: 103793-37-9
• 化学式: C₇H₇O₃S*C₁₂H₁₃N₂O₂
• 分子量: 388.444
• InChiKey: OKKZKZXCHNPLRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲苯磺酸甲酯 、 2-(1H-imidazol-1-yl)-3'-hydroxy acetophenone 以 乙腈 为溶剂， 以0.19 g的产率得到3-<2-(3-hydroxyphenyl)-2-oxoethyl>-1-methyl-1H-imidazolium 4-methylbenzenesulfonate
  参考文献：
  名称：

  Oral hypoglycemic agents. Discovery and structure-activity relationships of phenacylimidazolium halides

  摘要：

  Blood glucose levels in viable, yellow, obese, diabetic mice are reduced following oral administration of phenacylimidazolium halides. Compounds 2 and 3 produced reductions of ca. 40% 2 h after doses of 100 mg/kg po. Since these mice do not respond to sulfonylureas, the glucose-lowering activity of phenacylimidazolium salts in this model suggests a mechanism other than that of stimulating insulin secretion. Only phenacylimidazolium halides with electron-donating groups were active; other azolium salts or variations in the phenacyl portion (alterations in the keto function; chain lengthening or extensive branching) produced inactive compounds.

  DOI：

  10.1021/jm00130a013

文献信息

• 3-(2-Aryl-2-oxoethyl)-imidazolium salts as hypoglycemic agents
  申请人：ELI LILLY AND COMPANY

  公开号：EP0182533A2

  公开（公告）日：1986-05-28

  The invention relates to imidazolium salts which are effective in lowering blood glucose levels in mammals. In particular, there is provided a compound of formula (I) which is useful in lowering blood glucose levels: in which: R1 is C1-C4 alkyl; R2 and R3, independently, are hydrogen or C1-C4 alkyl; each R4, independently is, -OR5, -NR6R7, C1-C4 alkyl, C1-C4 alkoxy, trifluoromethyl, or C1-C4 alkylthio; R5 is hydrogen or R6 is hydrogen, C1-C4 alkyl, or -C-R8; R7 is hydrogen or C1-C4 alkyl; each R8, independently, is C1-C4 alkyl or phenyl; Z is oxygen or sulfur; X is a therapeutically acceptable anion; and m is 0, 1 or 2.

  本发明涉及可有效降低哺乳动物血糖水平的咪唑盐。 特别是提供了一种有助于降低血糖水平的式 (I) 化合物：其中： R1为C1-C4烷基；R2和R3独立地为氢或C1-C4烷基；每个R4独立地为-OR5、-NR6R7、C1-C4烷基、C1-C4烷氧基、三氟甲基或C1-C4烷硫基；R5为氢或R6为氢、C1-C4烷基或-C-R8；R7为氢或C1-C4烷基；每个R8独立地为C1-C4烷基或苯基；Z为氧或硫；X为治疗上可接受的阴离子；m为0、1或2。
• Oral hypoglycemic agents. Discovery and structure-activity relationships of phenacylimidazolium halides
  作者：Samuel J. Dominianni、Terence T. Yen

  DOI：10.1021/jm00130a013

  日期：1989.10

  Blood glucose levels in viable, yellow, obese, diabetic mice are reduced following oral administration of phenacylimidazolium halides. Compounds 2 and 3 produced reductions of ca. 40% 2 h after doses of 100 mg/kg po. Since these mice do not respond to sulfonylureas, the glucose-lowering activity of phenacylimidazolium salts in this model suggests a mechanism other than that of stimulating insulin secretion. Only phenacylimidazolium halides with electron-donating groups were active; other azolium salts or variations in the phenacyl portion (alterations in the keto function; chain lengthening or extensive branching) produced inactive compounds.