N-chloroacetyl-3,5-dimethyl-2,6-bis(p-methoxyphenyl)piperidin-4-one | 936097-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-chloroacetyl-3,5-dimethyl-2,6-bis(p-methoxyphenyl)piperidin-4-one
• 英文别名: 1-(2-Chloroacetyl)-2,6-bis(4-methoxyphenyl)-3,5-dimethyl-piperidin-4-one；1-(2-chloroacetyl)-2,6-bis(4-methoxyphenyl)-3,5-dimethylpiperidin-4-one
• CAS: 936097-25-5
• 化学式: C₂₃H₂₆ClNO₄
• 分子量: 415.917
• InChiKey: BBZZNMYUAVPSEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-chloroacetyl-3,5-dimethyl-2,6-bis(p-methoxyphenyl)piperidin-4-one 、 N-哌嗪甲酸乙酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 以74%的产率得到1-[2-(4-ethoxycarbonylpiperazin-1-yl)acetyl]-3,5-dimethyl-2,6-bis(p-methoxyphenyl)piperidin-4-one
  参考文献：
  名称：

  Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents

  摘要：

  A new series of 1-[2-(4-ethoxycarbonylpiperazine-1-yl)acetyl]-2,6-diarylpiperidin-4-ones (3a-3j) has been synthesized by conventional method and were characterized by IR, elemental analysis, mass spectral, 1 H NMR, C-13 NMR, and single crystal X-ray diffraction analysis. The synthesized compounds were evaluated for their antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC-27294) and also its antimicrobial activity were examined against five familiar bacterial and fungal strains. Among the synthesized compounds, compounds 3e-3j exhibit higher inhibition potency (16 mu g/ml) against M. tuberculosis H37Rv. Furthermore, compounds containing fluoro substituent in the phenyl ring at C-2 and C-6 positions of the piperidin-4-one motif (compounds 3c, 3d, and 3i) exerted better antibacterial and antifungal activity than the other phenyl-substituted compounds.

  DOI：

  10.1007/s00044-011-9573-9
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 ammonium acetate 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 N-chloroacetyl-3,5-dimethyl-2,6-bis(p-methoxyphenyl)piperidin-4-one
  参考文献：
  名称：

  某些N-吗啉代乙酰基2,6-二芳基哌啶-4-酮的合成，立体化学和抗菌性评估。

  摘要：

  为寻找有效的抗菌剂新途径，合成了一系列新型N-吗啉代乙酰基-2,6-二芳基哌啶-4-酮，它们对金黄色葡萄球菌，大肠杆菌，铜绿假单胞菌和鼠伤寒沙门氏菌和评估了对白色念珠菌，根霉菌，黑曲霉和黄曲霉的抗真菌活性。所有的N-吗啉代乙酰基-2,6-二芳基哌啶-4-酮的结构和立体化学已使用（1）H和（13）C NMR光谱技术进行了分析。在所有情况下，相对于哌啶酮环的动态平均平面，酰胺N-CO基团优选处于共面取向。此外，所有对称取代的化合物19、23、24，预期26和27将采用半舟构型，而其他化合物20-22和25将采用扭转舟构型。这九种化合物的结构活性关系结果表明，化合物26和27对除27种抗金黄色葡萄球菌外的所有细菌菌株均具有优异的抗菌活性。对白色念珠菌和黄曲霉，化合物24表现出优异的抗真菌活性，而对根霉属（Rhizopus sp。）而言，化合物25显示出强效活性。获得的结果可以用作构建具有与标准药

  DOI：

  10.1016/j.ejmech.2006.12.005

文献信息

• Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6-diarylpiperidin-4-ones
  作者：G. Aridoss、S. Balasubramanian、P. Parthiban、S. Kabilan

  DOI：10.1016/j.ejmech.2006.12.005

  日期：2007.6

  Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi and antifungal activity against Candida albicans, Rhizopus sp., Aspergillus niger and Aspergillus flavus were evaluated. Structure and stereochemistry of all the N-morpholinoacetyl-2,6-diarylpiperidin-4-ones have been analyzed using (1)H and (13)C NMR spectroscopic techniques. In all the cases, amide N-CO group is preferentially in coplanar orientation

  为寻找有效的抗菌剂新途径，合成了一系列新型N-吗啉代乙酰基-2,6-二芳基哌啶-4-酮，它们对金黄色葡萄球菌，大肠杆菌，铜绿假单胞菌和鼠伤寒沙门氏菌和评估了对白色念珠菌，根霉菌，黑曲霉和黄曲霉的抗真菌活性。所有的N-吗啉代乙酰基-2,6-二芳基哌啶-4-酮的结构和立体化学已使用（1）H和（13）C NMR光谱技术进行了分析。在所有情况下，相对于哌啶酮环的动态平均平面，酰胺N-CO基团优选处于共面取向。此外，所有对称取代的化合物19、23、24，预期26和27将采用半舟构型，而其他化合物20-22和25将采用扭转舟构型。这九种化合物的结构活性关系结果表明，化合物26和27对除27种抗金黄色葡萄球菌外的所有细菌菌株均具有优异的抗菌活性。对白色念珠菌和黄曲霉，化合物24表现出优异的抗真菌活性，而对根霉属（Rhizopus sp。）而言，化合物25显示出强效活性。获得的结果可以用作构建具有与标准药
• Synthesis and NMR spectral studies of N-chloroacetyl-2,6-diarylpiperidin-4-ones
  作者：G. Aridoss、S. Balasubramanian、P. Parthiban、S. Kabilan

  DOI：10.1016/j.saa.2007.01.013

  日期：2007.12

  N-chloroacetyl-2,6-diarylpiperidin-4-ones with and without alkyl substituent at C-3 and C-5 (8-14) have also been discussed using the spectral studies. The spectral data and extracted coupling constant values suggest that the compounds 8, 12 and 14 adopt flattened boat conformation whereas the remaining compounds exist in twist-boat conformations in solution with coplanar orientation of the chloroacetyl

  合成了在杂环氮上具有吸电子氯乙酰基的一系列2,6-二芳基哌啶-4-酮。通过一维（（1）H NMR和（13）C NMR）和二维（化合物8和9的HOMOCOSY，NOESY和HSQC光谱，以及仅10种的HOMOCOSY光谱）NMR光谱实现了合成化合物的明确表征数据。还使用光谱研究讨论了在C-3和C-5（8-14）处有或没有烷基取代基的N-氯乙酰基-2,6-二芳基哌啶-4-酮的构象偏好。光谱数据和提取的耦合常数值表明化合物8，图12和14采用扁平的舟状构象，而其余化合物以扭曲舟状构象存在于溶液中，其中杂环氮上存在的氯乙酰基部分共面取向。杂环碳上的氯乙酰基部分的取代基参数也已经根据它们的空间，电子和伽马蚀相互作用进行了推导和详细讨论。氮上的该取代基引起环碳和相关质子的化学位移发生实质性变化。
• Synthesis, spectral, crystal structure and in vitro antimicrobial evaluation of imidazole/benzotriazole substituted piperidin-4-one derivatives
  作者：R. Ramachandran、M. Rani、S. Senthan、Yeon Tae Jeong、S. Kabilan

  DOI：10.1016/j.ejmech.2011.02.036

  日期：2011.5

  Imidazole/benzotriazole analogues substituted piperidin-4-one derivatives (17–26) have been synthesized. Their chemical structures were characterized by IR, 1H NMR, 13C NMR and mass spectral analysis. In addition, single crystal X-ray diffraction has also been recorded for compounds 21 and 23. The synthesized compounds were subjected to their in vitro antibacterial and antifungal activities against

  已合成了咪唑/苯并三唑类似物取代的哌啶-4-一衍生物（17-26）。通过IR，1 H NMR，13 C NMR和质谱分析对它们的化学结构进行表征。另外，还已经记录了化合物21和23的单晶X射线衍射。合成的化合物具有针对病原性微生物菌株的体外抗菌和抗真菌活性。结果指出，针对枯草芽孢杆菌的化合物19和24和针对大肠杆菌的化合物20和24 探索了优异的抑制活性。
• A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives
  作者：Gopalakrishnan Aridoss、Shanmugasundaram Amirthaganesan、Nanjundan Ashok Kumar、Jong Tae Kim、Kwon Taek Lim、Senthamaraikannan Kabilan、Yeon Tae Jeong

  DOI：10.1016/j.bmcl.2008.10.045

  日期：2008.12

  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.
• Synthesis and antimicrobial activities of N-chloroacetyl-2,6-diarylpiperidin-4-ones
  作者：G. Aridoss、S. Balasubramanian、P. Parthiban、R. Ramachandran、S. Kabilan

  DOI：10.1007/s00044-007-9023-x

  日期：2007.9

  An array of new N-chloroacetyl-2,6-diarylpiperidin-4-ones has been synthesised and their antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa, and Salmonella typhi, and antifungal activity against Cryptococcus neoformans, Candida albicans, Rhizopus sp., Aspergillus flavus, and Aspergillus niger examined. Compounds 14 against P. aeruginosa, 15 against S. typhi, 16 against S. aureus, and 19 against B. subtilis showed marked antibacterial activity. Similarly, compounds 15 and 19 against A. niger and 19 against A. flavus exerted significant antifungal activities.