potassium (E)-2-oxo-4-(pyridin-3-yl)but-3-enoate

• 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: potassium (E)-2-oxo-4-(pyridin-3-yl)but-3-enoate
• 英文别名: potassium;(E)-2-oxo-4-pyridin-3-ylbut-3-enoate
• 化学式: C₉H₆NO₃*K
• 分子量: 215.25
• InChiKey: DZFFVTFRAAKDNB-BJILWQEISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.58
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium (E)-2-oxo-4-(pyridin-3-yl)but-3-enoate 在 palladium on activated charcoal 、 氢气 作用下， 以 异丙醇 为溶剂， 生成 2-oxo-4-(pyridin-3-yl)butanoic acid
  参考文献：
  名称：

  [EN] MIP INHIBITORS
  [FR] INHIBITEURS DE MIP

  摘要：

  本公开一般涉及哌啶醇酸衍生化合物，特别是式(I)的哌啶醇酸衍生化合物，以及包含这些化合物的制剂和组合物。本公开还涉及这些化合物、组合物和/或制剂在治疗和/或预防由病原体介导的疾病或病症中的方法和用途，病原体对巨噬细胞感染性增效剂（Mip）蛋白的抑制反应敏感，和/或Mip蛋白是毒力因子的疾病或病症介导。

  公开号：

  WO2023178378A1
• 作为产物：
  描述：

  3-吡啶甲醛 、 丙酮酸 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以61%的产率得到potassium (E)-2-oxo-4-(pyridin-3-yl)but-3-enoate
  参考文献：
  名称：

  2-羟基-3-烯酸钾可作为NHC催化的不对称反应中α，β-不饱和醛的有效且多用途的替代物

  摘要：

  2-羟基-3-烯酸钾很容易大规模制备并易于储存，已被发现是NHC催化的不对称反应中α，β-不饱和醛的有效且多用途的替代物。这些易处理的固体盐在手性N-杂环卡宾与LiCl的共同作用下可以释放出CO 2，然后通过同烯酸酯和α，β-不饱和酰基偶氮中间体发生不对称反应。反应具有高对映选择性的广泛的底物范围。

  DOI：

  10.1002/adsc.201701413

文献信息

• Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition−Lactonizations
  作者：Dorine Belmessieri、Louis C. Morrill、Carmen Simal、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/ja109975c

  日期：2011.3.2

  Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).
• Diaryl Dihydropyrazole-3-carboxamides with Significant In Vivo Antiobesity Activity Related to CB1 Receptor Antagonism:  Synthesis, Biological Evaluation, and Molecular Modeling in the Homology Model
  作者：Brijesh Kumar Srivastava,*、Amit Joharapurkar、Saurin Raval、Jayendra Z. Patel、Rina Soni、Preeti Raval、Archana Gite、Amitgiri Goswami、Nisha Sadhwani、Neha Gandhi、Harilal Patel、Bhupendra Mishra、Manish Solanki、Bipin Pandey、Mukul R. Jain、Pankaj R. Patel

  DOI：10.1021/jm061490u

  日期：2007.11.1

  A number of analogues of diaryl dihydropyrazole-3-carboxamides have been synthesized. Their activities were evaluated for appetite suppression and body weight reduction in animal models. Depending on the chemical modification of the selected dihydropyrazole scaffold, the lead compounds-the bisulfate salt,of (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 26 and the bisulfate salt of (-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole3-carboxylic acid morpholin-4-ylamide 30-showed significant body weight reduction in vivo, which is attributed to their CB1 antagonistic activity and exhibited a favorable pharmacokinetic profile. The molecular modeling studies also showed interactions of two isomers of (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)4,5-dihydro- 1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 9 with CB I receptor in the homology model similar to those of N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-3-pyrazole-carboxarnide (rimonabant) 1 and 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-pheny1-4,5-dihydro-1H-pyrazole-1-carboxamidine (SLV-319) 2.
• Analysis of Structure–Activity Relationships of Novel Inhibitors of the Macrophage Infectivity Potentiator (Mip) Proteins of <i>Neisseria meningitidis</i>, <i>Neisseria gonorrhoeae</i>, and <i>Burkholderia pseudomallei</i>
  作者：Nicolas J. Scheuplein、Nicole M. Bzdyl、Theresa Lohr、Emily A. Kibble、Anja Hasenkopf、Carina Herbst、Mitali Sarkar-Tyson、Ulrike Holzgrabe

  DOI：10.1021/acs.jmedchem.3c00458

  日期：2023.7.13