N-chloroacetyl-3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine | 1103231-24-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: N-chloroacetyl-3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine
• 英文别名: Ethyl 1-(chloroacetyl)-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 1-(2-chloroacetyl)-4-hydroxy-2,6-diphenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1103231-24-8
• 化学式: C₂₂H₂₂ClNO₄
• 分子量: 399.874
• InChiKey: OLZUOULUTZTBDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-chloroacetyl-3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine 、 3-硝基苯磺酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到N-chloroacetyl-3-carboxyethyl-2,6-diphenyl-4-O-(3-nitro-benzenesulfonyl)-Δ3-tetrahydropyridine
  参考文献：
  名称：

  A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives

  摘要：

  The raise in clinical significance of multidrug-resistant bacterial pathogens has directed us to synthesize 2,6-diarylpiperidin-4-one and Delta(3)-tetrahydropyridin-4-ol based benzimidazole and O-arylsulfonyl derivatives. X-ray crystal structure of tetrahydropyridinol (23) confirmed a change in conformation and orientation of substituents upon amide formation. Antibacterial activities evaluated against a wide number of bacterial pathogens (both sensitive and multidrug-resistant) revealed that 19, 27 against Staphylococcus aureus, 27 against Enterococcus faecalis, and 19, 21, 23, and 27 against Enterococcus faecium are significantly good at lowest MIC90 (16 mu g/mL). Inhibitory power noticed by 23 against Vancomycin-Linezolid-resistant E. faecalis and 27 against Vancomycin-resistant E. faecium are onefold better than the standard Linezolid and Trovafloxacin drugs, respectively. Moreover, antitubercular activity for the selected compounds against Mycobacterium tuberculosis H37Rv revealed that compounds 23, 24, and 27 expressed onefold improved potency compared to the standard Rifampicin drug. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.045
• 作为产物：
  描述：

  2,6-diphenyl-3-carboethoxypiperidin-4-one 、 氯乙酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 反应 4.0h， 以96%的产率得到N-chloroacetyl-3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine
  参考文献：
  名称：

  A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives

  摘要：

  The raise in clinical significance of multidrug-resistant bacterial pathogens has directed us to synthesize 2,6-diarylpiperidin-4-one and Delta(3)-tetrahydropyridin-4-ol based benzimidazole and O-arylsulfonyl derivatives. X-ray crystal structure of tetrahydropyridinol (23) confirmed a change in conformation and orientation of substituents upon amide formation. Antibacterial activities evaluated against a wide number of bacterial pathogens (both sensitive and multidrug-resistant) revealed that 19, 27 against Staphylococcus aureus, 27 against Enterococcus faecalis, and 19, 21, 23, and 27 against Enterococcus faecium are significantly good at lowest MIC90 (16 mu g/mL). Inhibitory power noticed by 23 against Vancomycin-Linezolid-resistant E. faecalis and 27 against Vancomycin-resistant E. faecium are onefold better than the standard Linezolid and Trovafloxacin drugs, respectively. Moreover, antitubercular activity for the selected compounds against Mycobacterium tuberculosis H37Rv revealed that compounds 23, 24, and 27 expressed onefold improved potency compared to the standard Rifampicin drug. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.045