4,N-dicyclohexyl-N-methyl-4-oxo-butyramide

• 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: 4,N-dicyclohexyl-N-methyl-4-oxo-butyramide
• 英文别名: N-Cyclohexyl-N-methyl-gamma-oxocyclohexanebutanamide；N,4-dicyclohexyl-N-methyl-4-oxobutanamide
• 化学式: C₁₇H₂₉NO₂
• 分子量: 279.423
• InChiKey: CENMYNLXXACMIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  4,N-dicyclohexyl-N-methyl-4-oxo-butyramide 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 4-amino-4,N-dicyclohexyl-N-methyl-butyramide
  参考文献：
  名称：

  2-Amino-3,4-dihydroquinazolines as Inhibitors of BACE-1 (β-Site APP Cleaving Enzyme):  Use of Structure Based Design to Convert a Micromolar Hit into a Nanomolar Lead

  摘要：

  A new aspartic protease inhibitory chemotype bearing a 2-amino-3,4-dihydroquinazoline ring was identified by high-throughput screening for the inhibition of BACE-1. X-ray crystallography revealed that the exocyclic amino group participated in a hydrogen bonding array with the two catalytic aspartic acids of BACE-1 (Asp(32), Asp(228)). BACE-1 inhibitory potency was increased (0.9 mu M to 11 nM K-i) by substitution into the unoccupied S-1 ' pocket.

  DOI：

  10.1021/jm0705408
• 作为产物：
  描述：

  N-甲基环己胺 、 4-环己基-4-氧代丁酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 以25%的产率得到4,N-dicyclohexyl-N-methyl-4-oxo-butyramide
  参考文献：
  名称：

  [EN] SUBSTITUTED AMINO-BENZIMIDAZOLES, MEDICAMENTS COMPRISING SAID COMPOUND, THEIR USE AND THEIR METHOD OF MANUFACTURE
  [FR] AMINO-BENZIMIDAZOLES SUBSTITUÉS, MÉDICAMENTS COMPRENANT LEDIT COMPOSÉ, LEUR UTILISATION ET LEUR PROCÉDÉ DE FABRICATION

  摘要：

  本发明涉及一般式（1）中的取代氨基苯并咪唑，其中基团R1至R14和A如规范和索赔中定义，并其用于治疗阿尔茨海默病（AD）和类似疾病。

  公开号：

  WO2009092566A1

文献信息

• [EN] SUBSTITUTED AMINO-BENZIMIDAZOLES, MEDICAMENTS COMPRISING SAID COMPOUND, THEIR USE AND THEIR METHOD OF MANUFACTURE<br/>[FR] AMINO-BENZIMIDAZOLES SUBSTITUÉS, MÉDICAMENTS COMPRENANT LEDIT COMPOSÉ, LEUR UTILISATION ET LEUR PROCÉDÉ DE FABRICATION
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009092566A1

  公开（公告）日：2009-07-30

  The present invention relates to substituted amino-benzimidazoles of general formula (1) wherein the groups R1 to R14 and A, are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.

  本发明涉及一般式（1）中的取代氨基苯并咪唑，其中基团R1至R14和A如规范和索赔中定义，并其用于治疗阿尔茨海默病（AD）和类似疾病。
• SUBSTITUTED AMINO-BENZIMIDAZOLES, MEDICAMENTS COMPRIMISING SAID COMPOUND, THEIR USE AND THEIR METHOD OF MANUFACTURE
  申请人：Fuchs Klaus

  公开号：US20110288139A1

  公开（公告）日：2011-11-24

  The present invention relates to substituted amino-benzimidazoles of general formula (1) wherein the groups R 1 to R 14 and A, are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.
• US8426607B2
  申请人：——

  公开号：US8426607B2

  公开（公告）日：2013-04-23
• 2-Amino-3,4-dihydroquinazolines as Inhibitors of BACE-1 (β-Site APP Cleaving Enzyme):  Use of Structure Based Design to Convert a Micromolar Hit into a Nanomolar Lead
  作者：Ellen W. Baxter、Kelly A. Conway、Ludo Kennis、François Bischoff、Marc H. Mercken、Hans L. De Winter、Charles H. Reynolds、Brett A. Tounge、Chi Luo、Malcolm K. Scott、Yifang Huang、Mirielle Braeken、Serge M. A. Pieters、Didier J. C. Berthelot、Stefan Masure、Wouter D. Bruinzeel、Alfonzo D. Jordan、Michael H. Parker、Robert E. Boyd、Junya Qu、Richard S. Alexander、Douglas E. Brenneman、Allen B. Reitz

  DOI：10.1021/jm0705408

  日期：2007.9.1

  A new aspartic protease inhibitory chemotype bearing a 2-amino-3,4-dihydroquinazoline ring was identified by high-throughput screening for the inhibition of BACE-1. X-ray crystallography revealed that the exocyclic amino group participated in a hydrogen bonding array with the two catalytic aspartic acids of BACE-1 (Asp(32), Asp(228)). BACE-1 inhibitory potency was increased (0.9 mu M to 11 nM K-i) by substitution into the unoccupied S-1 ' pocket.