3-hydroxy-3-methylglutaric acid monomethyl ester amide | 72060-93-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-hydroxy-3-methylglutaric acid monomethyl ester amide
• 英文别名: 3-Hydroxy-3-methylglutaric acid monoamide methyl ester；methyl 5-amino-3-hydroxy-3-methyl-5-oxopentanoate
• CAS: 72060-93-6
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: TYWSHLIBAPKAHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-methylglutaric acid monomethyl ester amide 在 水 作用下， 以 sodium hydroxide 、 水 为溶剂， 反应 24.0h， 以to afford 3-hydroxy-3-methylglutaric acid monoamide的产率得到3-hydroxy-3-methylglutaric acid monoamide
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaric acid monoamide and derivatives thereof

  摘要：

  披露的新化合物为3-羟基-3-甲基戊二酸单酰胺及其较低烷基酯和盐，3-羟基-3-甲基戊二酰胺单腈和3-羟基-3-甲基戊二酰胺。3-羟基-3-甲基戊二酸单酰胺及其衍生物对多种多年生和一年生杂草具有抗萌发和抗生长效用。3-羟基-3-甲基戊二酰胺单腈和3-羟基-3-甲基戊二酰胺在3-羟基-3-甲基戊二酸单酰胺的制备中具有中间体的作用。

  公开号：

  US04208204A1
• 作为产物：
  描述：

  3-羟基-3-甲基戊二酸酐 在 氨 、 potassium carbonate 、 碘甲烷 作用下， 生成 3-hydroxy-3-methylglutaric acid monomethyl ester amide 、 3-hydroxy-3-methylglutarimide
  参考文献：
  名称：

  3-Alkyl-3-hydroxyglutaric Acids: A New Class of Hypocholesterolemic HMG CoA Reductase Inhibitors. 1

  摘要：

  Derivatives of 3-hydroxy-3-methylglutaric acid (HMG), a portion of the substrate for HMG CoA reductase, were prepared and tested for their inhibitory action against rat liver HMG CoA reductase and for their hypocholesterolemic activity. Structure-dependent competitive inhibition was observed. Optimal structures had a free dicarboxylic acid with an alkyl group of 13-16 carbons at position 3. 3-n-Pentadecyl-3-hydroxyglutaric acid (3j) (IC50 = 50 microM) reduced serum cholesterol in the Triton-treated rat and HMG CoA reductase activity in the 20,25-diazacholesterol-treated rat.

  DOI：

  10.1021/jm50001a011

文献信息

• 3-Hydroxy-3-methylglutaric acid monoamide, derivatives thereof, intermediates, methods of preparation and compositions
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0001450A2

  公开（公告）日：1979-04-18

  Disclosed as novel compounds are 3-hydroxy-3-methylglutaric acid monoamide and the lower alkyl esters and salts thereof, 3-hydroxy-3-methylglutaramide mononitrile and 3-hydroxy-3-methylglutaramide. 3-Hydroxy-3-methylglutaric acid monoamide and derivatives thereof exhibit anti-germination and anti-growth utility against a wide variety of perennial and annual weed grasses and have furthermore pharmaceutical utility as serum lipid lowering agents. 3-Hydroxy-3-methylglutaramide mononitrile and 3-hydroxy-3-methylglutaramide have utility as intermediates in the preparation of 3-hydroxy-3-methylglutaric acid monoamide.

  作为新型化合物公开的是 3-羟基-3-甲基戊二酸单酰胺及其低级烷基酯和盐、3-羟基-3-甲基戊二酸单腈盐、3-羟基-3-甲基戊二酸单酰胺。3- 羟基-3-甲基戊二酸单酰胺及其衍生物对多种多年生和一年生杂草具有抗发芽和抗生长的作用，还可作为降血脂药物使用。3-羟基-3-甲基戊二酰胺单腈和 3-羟基-3-甲基戊二酰胺可用作制备 3-羟基-3-甲基戊二酸单酰胺的中间体。
• US4208204A
  申请人：——

  公开号：US4208204A

  公开（公告）日：1980-06-17
• 3-Alkyl-3-hydroxyglutaric Acids: A New Class of Hypocholesterolemic HMG CoA Reductase Inhibitors. 1
  作者：John S. Baran、Ivar Laos、Donna D. Langford、James E. Miller、Charlene Jett、Beatrice Taite、Elaine Rohrbacher

  DOI：10.1021/jm50001a011

  日期：1985.5

  Derivatives of 3-hydroxy-3-methylglutaric acid (HMG), a portion of the substrate for HMG CoA reductase, were prepared and tested for their inhibitory action against rat liver HMG CoA reductase and for their hypocholesterolemic activity. Structure-dependent competitive inhibition was observed. Optimal structures had a free dicarboxylic acid with an alkyl group of 13-16 carbons at position 3. 3-n-Pentadecyl-3-hydroxyglutaric acid (3j) (IC50 = 50 microM) reduced serum cholesterol in the Triton-treated rat and HMG CoA reductase activity in the 20,25-diazacholesterol-treated rat.
• 3-Hydroxy-3-methylglutaric acid monoamide and derivatives thereof
  申请人：Calbiochem-Behring Corp.

  公开号：US04208204A1

  公开（公告）日：1980-06-17

  Disclosed as novel compounds are 3-hydroxy-3-methylglutaric acid monoamide and the lower alkyl esters and salts thereof, 3-hydroxy-3-methylglutaramide mononitrile and 3-hydroxy-3-methylglutaramide. 3-Hydroxy-3-methylglutaric acid monoamide and derivatives thereof exhibit anti-germination and anti-growth utility against a wide variety of perennial and annual weed grasses. 3-Hydroxy-3-methylglutaramide mononitrile and 3-hydroxy-3-methylglutaramide have utility as intermediates in the preparation of 3-hydroxy-3-methylglutaric acid monoamide.

  披露的新化合物为3-羟基-3-甲基戊二酸单酰胺及其较低烷基酯和盐，3-羟基-3-甲基戊二酰胺单腈和3-羟基-3-甲基戊二酰胺。3-羟基-3-甲基戊二酸单酰胺及其衍生物对多种多年生和一年生杂草具有抗萌发和抗生长效用。3-羟基-3-甲基戊二酰胺单腈和3-羟基-3-甲基戊二酰胺在3-羟基-3-甲基戊二酸单酰胺的制备中具有中间体的作用。