N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-hexadecanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-hexadecanamide
• 英文别名: N-[2,6-di(propan-2-yl)phenyl]-3-oxohexadecanamide
• 化学式: C₂₈H₄₇NO₂
• 分子量: 429.687
• InChiKey: NFBCWKGHSOJOFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 3-oxohexadecanoate 在 三乙烯二胺 、 lithium diisopropyl amide 作用下， 以 xylene 为溶剂， 反应 21.33h， 生成 N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-hexadecanamide
  参考文献：
  名称：

  Inhibitors of acyl-CoA:cholesterol acyltransferase. 5. Identification and structure-activity relationships of novel .beta.-keto amides as hypocholesterolemic agents

  摘要：

  A study of structure-activity relationships of substituted beta-ketoamide ACAT inhibitors I and II was performed. The results of this study suggest that whereas the beta-keto group was tolerated with no loss in activity, beta-hydroxy and oxime moieties led to significantly reduced activity in vitro and in vivo. The most potent inhibitor from the acyclic series (I) (11, IC50 = 0.006 muM) contained a C-13 alkyl chain. This compound reduced plasma total cholesterol by 38% and 66% at 3 and 30 mg/kg, respectively, in cholesterol-fed rats. Dimethylation alpha to the anilide core(5) and subsequent N-methylation of the amide NH (6) decreased in vitro potency significantly. It was also found that high potency was retained with inhibitors which incorporated the carbonyl into a lactam ring (II).

  DOI：

  10.1021/jm00072a014
• 作为试剂：
  描述：

  2-十五烷酮 、 2,6-二异丙基苯异氰酸酯 、 lithium diisopropyl amide 在 N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-hexadecanamide 、 silica gel 、 ethyl acetate n-hexane 作用下， 以yielded 1.92 g (0.004, 34%) of the desired product的产率得到N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-hexadecanamide
  参考文献：
  名称：

  Substituted beta-ketoamide ACAT inhibitors

  摘要：

  一种降低血液胆固醇水平的新型药用化合物，其为β-酮酰胺、肟、胺和其羟基衍生物。

  公开号：

  US05278326A1

文献信息

• METHOD FOR DECREASING SEBUM PRODUCTION
  申请人：Kostlan Catherine R.

  公开号：US20100113601A1

  公开（公告）日：2010-05-06

  The present invention is directed to the topical application of the malonamide ACAT inhibitors described by Formula I. Other aspects of the invention are directed to topical formulations of these diamides, their use to treat sebaceous gland disorders and their use to alleviate oily skin.
• US5278326A
  申请人：——

  公开号：US5278326A

  公开（公告）日：1994-01-11
• US7615230B2
  申请人：——

  公开号：US7615230B2

  公开（公告）日：2009-11-10
• US8409595B2
  申请人：——

  公开号：US8409595B2

  公开（公告）日：2013-04-02
• Inhibitors of acyl-CoA:cholesterol acyltransferase. 5. Identification and structure-activity relationships of novel .beta.-keto amides as hypocholesterolemic agents
  作者：Corinne E. Augelli-Szafran、C. John Blankley、Bruce D. Roth、Bharat K. Trivedi、Richard F. Bousley、Arnold D. Essenburg、Katherine L. Hamelehle、Brian R. Krause、Richard L. Stanfield

  DOI：10.1021/jm00072a014

  日期：1993.10

  A study of structure-activity relationships of substituted beta-ketoamide ACAT inhibitors I and II was performed. The results of this study suggest that whereas the beta-keto group was tolerated with no loss in activity, beta-hydroxy and oxime moieties led to significantly reduced activity in vitro and in vivo. The most potent inhibitor from the acyclic series (I) (11, IC50 = 0.006 muM) contained a C-13 alkyl chain. This compound reduced plasma total cholesterol by 38% and 66% at 3 and 30 mg/kg, respectively, in cholesterol-fed rats. Dimethylation alpha to the anilide core(5) and subsequent N-methylation of the amide NH (6) decreased in vitro potency significantly. It was also found that high potency was retained with inhibitors which incorporated the carbonyl into a lactam ring (II).