5-ethyl 1-methyl-4-(1-aminopentylidene)pent-2-enedioate | 1024037-46-4

• 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: 5-ethyl 1-methyl-4-(1-aminopentylidene)pent-2-enedioate
• 英文别名: 5-O-ethyl 1-O-methyl 4-(1-aminopentylidene)pent-2-enedioate
• CAS: 1024037-46-4
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: SYSQLQYCQSSOIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-ethyl 1-methyl-4-(1-aminopentylidene)pent-2-enedioate 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 sodium t-butanolate 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 丁腈 、 二氯甲烷 为溶剂， 反应 134.0h， 生成 2-[(3S)-1-[6-butyl-5-(cyclohexylcarbamoyl)pyridin-2-yl]-3-piperidyl]acetic acid
  参考文献：
  名称：

  Discovery of a Potent, Selective, and Orally Bioavailable Acidic 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Inhibitor: Discovery of 2-[(3S)-1-[5-(Cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-3-piperidyl]acetic Acid (AZD4017)

  摘要：

  Inhibition of 11 beta-HSD1 is an attractive mechanism for the treatment of obesity and other elements of the metabolic syndrome. We report here the discovery of a nicotinic amide derived carboxylic acid class of inhibitors that has good potency, selectivity, and pharmacokinetic characteristics. Compound 11i (AZD4017) is an effective inhibitor of 11 beta-HSD1 in human adipocytes and exhibits good druglike properties and as a consequence was selected for clinical development.

  DOI：

  10.1021/jm300592r
• 作为产物：
  描述：

  ethyl 3-amino-2-heptenoate 、 丙炔酸甲酯 以 甲苯 为溶剂， 反应 96.0h， 以81%的产率得到5-ethyl 1-methyl-4-(1-aminopentylidene)pent-2-enedioate
  参考文献：
  名称：

  CHEMICAL COMPOUNDS

  摘要：

  公式（I）的化合物：其中变量基团在内部定义；描述了它们在抑制11βHSD1中的应用，制备它们的过程以及包含它们的药物组合物。

  公开号：

  US20080269288A1

文献信息

• CHEMICAL COMPOUNDS
  申请人：McCoull William

  公开号：US20080269288A1

  公开（公告）日：2008-10-30

  Compounds of formula (I): wherein variable groups are defined within; their use in the inhibition of 11βHSD1, processes for making them and pharmaceutical compositions comprising them are described.

  公式（I）的化合物：其中变量基团在内部定义；描述了它们在抑制11βHSD1中的应用，制备它们的过程以及包含它们的药物组合物。
• Discovery of a Potent, Selective, and Orally Bioavailable Acidic 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Inhibitor: Discovery of 2-[(3<i>S</i>)-1-[5-(Cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-3-piperidyl]acetic Acid (AZD4017)
  作者：James S. Scott、Suzanne S. Bowker、Joanne deSchoolmeester、Stefan Gerhardt、David Hargreaves、Elaine Kilgour、Adele Lloyd、Rachel M. Mayers、William McCoull、Nicholas J. Newcombe、Derek Ogg、Martin J. Packer、Amanda Rees、John Revill、Paul Schofield、Nidhal Selmi、John G. Swales、Paul R. O. Whittamore

  DOI：10.1021/jm300592r

  日期：2012.6.28

  Inhibition of 11 beta-HSD1 is an attractive mechanism for the treatment of obesity and other elements of the metabolic syndrome. We report here the discovery of a nicotinic amide derived carboxylic acid class of inhibitors that has good potency, selectivity, and pharmacokinetic characteristics. Compound 11i (AZD4017) is an effective inhibitor of 11 beta-HSD1 in human adipocytes and exhibits good druglike properties and as a consequence was selected for clinical development.