6-benzyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid | 56304-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-benzyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid
• 英文别名: 6-benzyl-1,2-dihydro-2-oxonicotinic acid；6-benzyl-2-oxo-1H-pyridine-3-carboxylic acid
• CAS: 56304-31-5
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: XMPMOUPARVQARF-UHFFFAOYSA-N

物化性质

• 沸点：
  501.8±50.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-benzyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 在 二苯基磷酸 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 6-benzyl-3(benzyloxycarbonylamino) pyrid-2-one
  参考文献：
  名称：

  Nonpeptidic Inhibitors of Human Leukocyte Elastase. 2. Design, Synthesis, and in vitro Activity of a Series of 3-Amino-6-aryl-2-oxopyridyl Trifluoromethyl Ketones

  摘要：

  A series of potent nonpeptidic inhibitors of the enzyme human leukocyte elastase (HLE) is reported. These inhibitors contain a 3-amino-2-pyridone ring as a central template in which the pyridone carbonyl and 3-position NH group are thought to form important hydrogen bonding interactions with the Val-216 residue of HLE. Substitution of the 6-position of the pyridone ring by various alkyl and aryl groups was found to afford increases in the in vitro potency of these inhibitors. A 6-position phenyl group, compound 10f, was found to result in a large increase in binding affinity, which was not obtained when the phenyl group was placed in either the 4- or 5-position of the molecule. Compound 10f was found to have good selectivity for HLE over other proteolytic enzymes, with the exception of bovine pancreatic chymotrypsin (BPC). Substitution of the 6-phenyl group in these molecules was found to decrease binding affinity for BPC without adversely affecting affinity for HLE.

  DOI：

  10.1021/jm00046a015
• 作为产物：
  描述：

  苯基丙酮 在 氢溴酸 、 sodium methylate 、 哌啶乙酸盐 作用下， 以 溶剂黄146 为溶剂， 生成 6-benzyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid
  参考文献：
  名称：

  Nonpeptidic Inhibitors of Human Leukocyte Elastase. 2. Design, Synthesis, and in vitro Activity of a Series of 3-Amino-6-aryl-2-oxopyridyl Trifluoromethyl Ketones

  摘要：

  A series of potent nonpeptidic inhibitors of the enzyme human leukocyte elastase (HLE) is reported. These inhibitors contain a 3-amino-2-pyridone ring as a central template in which the pyridone carbonyl and 3-position NH group are thought to form important hydrogen bonding interactions with the Val-216 residue of HLE. Substitution of the 6-position of the pyridone ring by various alkyl and aryl groups was found to afford increases in the in vitro potency of these inhibitors. A 6-position phenyl group, compound 10f, was found to result in a large increase in binding affinity, which was not obtained when the phenyl group was placed in either the 4- or 5-position of the molecule. Compound 10f was found to have good selectivity for HLE over other proteolytic enzymes, with the exception of bovine pancreatic chymotrypsin (BPC). Substitution of the 6-phenyl group in these molecules was found to decrease binding affinity for BPC without adversely affecting affinity for HLE.

  DOI：

  10.1021/jm00046a015

文献信息

• Substituted N-(1,2-dihydro-2-oxonicotinyl)-cephalexins and
  申请人：Parke, Davis & Company

  公开号：US03948903A1

  公开（公告）日：1976-04-06

  Novel organic amide compounds which are substituted N-(1,2-dihydro-2-oxonicotinyl)-ampicillins, -cephalexins and -cephaloglycins having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid ampicillin, cephalexin or cephaloglycin or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding 1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-aminopenicillanic acid, 7-aminocephalosporanic acid or 7-amino-3-methylceph-3-em-4-carboxylic acid or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding N-(1,2-dihydro-2-oxonicotinyl)-2-phenylglycine.

  新型有机酰胺化合物，其为取代的N-(1,2-二氢-2-氧基烟酸基)-氨苄青霉素、头孢氨苄和头孢甘露醇，具有广谱抗菌作用，通过(a)将游离氨基酸氨苄青霉素、头孢氨苄或头孢甘露醇或其酸盐或硅烷衍生物与相应的1,2-二氢-2-氧基烟酸的反应衍生物反应，或(b)将游离氨基酸6-氨基青霉素酸、7-氨基头孢菌素酸或7-氨基-3-甲基头孢-3-烯-4-羧酸或其酸盐或硅烷衍生物与相应的N-(1,2-二氢-2-氧基烟酸基)-2-苯基甘氨酸的反应衍生物反应。
• QUINOLINE COMPOUNDS AND METHODS OF USE
  申请人：Array Biopharma, Inc.

  公开号：EP2032538A2

  公开（公告）日：2009-03-11
• MODULATORS OF C3A RECEPTOR AND METHODS OF USE THEREOF
  申请人：ENCYSIVE PHARMACEUTICALS, INC.

  公开号：EP2125739A1

  公开（公告）日：2009-12-02
• PYRROLOTRIAZINE COMPOUNDS AS TAM INHIBITORS
  申请人：Incyte Corporation

  公开号：EP3436461A1

  公开（公告）日：2019-02-06
• US3948903A
  申请人：——

  公开号：US3948903A

  公开（公告）日：1976-04-06