N-chloroacetyl-3,5-dimethyl-2,6-bis(p-methylphenyl)piperidin-4-one | 936097-26-6

• 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-methylphenyl)piperidin-4-one
• 英文别名: 1-(2-Chloroacetyl)-3,5-dimethyl-2,6-bis(p-tolyl)piperidin-4-one；1-(2-chloroacetyl)-3,5-dimethyl-2,6-bis(4-methylphenyl)piperidin-4-one
• CAS: 936097-26-6
• 化学式: C₂₃H₂₆ClNO₂
• 分子量: 383.918
• InChiKey: ZBCVQQXIRKHYLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-chloroacetyl-3,5-dimethyl-2,6-bis(p-methylphenyl)piperidin-4-one 、 苯并咪唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到1-[2-(1H-benzimidazol-1-yl)acetyl]-3,5-dimethyl-2,6-bis(4-methylphenyl)piperidin-4-one
  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：

  3-戊酮 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-methylphenyl)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 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.
• Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: Antimicrobial, analgesic and antipyretic studies
  作者：G. Aridoss、P. Parthiban、R. Ramachandran、M. Prakash、S. Kabilan、Yeon Tae Jeong

  DOI：10.1016/j.ejmech.2008.03.031

  日期：2009.2

  A series of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones (13c-21c) were synthesized by the base catalyzed nucleophilic substitution of N-chloroacetyl-2,6-diarylpiperidin-4-ones obtained from their corresponding 2,6-diarylpiperidin-4-ones with N-methylpiperazine. These newly synthesized compounds were characterized by one- and two-dimensional NMR spectral studies. In all the cases, the piperazine ring adopted normal chair conformation with equatorial orientation of methyl group irrespective of the non-chair conformations of the piperidin-4-one moiety. All the compounds were screened for their possible antibacterial and antifungal activities against a spectrum of microbial agents besides analgesic and antipyretic activities. These biological studies proved that compounds 17c/18c against bacterial and 18c/20c against fungal strains exhibited promising antimicrobial activities whereas 17c/19c and 18c/19c showed beneficial analgesic and antipyretic profiles, respectively, at a concentration of 60 mg/kg and were also found to be more potent than the reference drug. (C) 2008 Elsevier Masson SAS. All fights reserved.
• Synthesis of Novel N‐Morpholinoacetyl‐2,6‐diarylpiperidin‐4‐ones
  作者：G. Aridoss、S. Balasubramanian、P. Parthiban、S. Kabilan

  DOI：10.1080/00397910601163828

  日期：2007.3.1

  A series of N-chloroacetyl-2,6-diarylpiperidin-4-ones (10-18) obtained from the corresponding 2,6-diarylpiperidin-4-ones upon base-catalyzed condensation with morpholine afforded N-morpholinoacetyl-2,6-diarylpiperidin-4-ones (19-27). The synthesized compounds have been characterized by their elemental, analytical, and spectral data.
• 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, 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