2,6-Bis(4-chlorophenyl)piperidin-4-one | 597577-90-7

• 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: 2,6-Bis(4-chlorophenyl)piperidin-4-one
• CAS: 597577-90-7
• 化学式: C₁₇H₁₅Cl₂NO
• 分子量: 320.218
• InChiKey: RPLOEIIZAYQBAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-Bis(4-chlorophenyl)piperidin-4-one 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-(2,6-bis(4-chlorophenyl)piperidin-4-ylideneamino)-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  A facile microwave assisted green chemical synthesis of novel piperidino 2-thioxoimidazolidin-4-ones and theirin vitromicrobiological evaluation

  摘要：

  A series of novel hybrid heterocyclic compounds, 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones were synthesised and a comparative study was also carried out under microwave irradiation. The synthesised compounds were characterised by their melting points, elemental analysis, MS, FT-IR, one-dimensional NMR (1H, D2O exchanged 1H and

  DOI：

  10.3109/14756361003691878
• 作为产物：
  描述：

  2,6-bis(4-chlorophenyl)piperidin-4-one hydrochloride 在 氨 作用下， 以 水 为溶剂， 生成 2,6-Bis(4-chlorophenyl)piperidin-4-one
  参考文献：
  名称：

  Synthesis, spectral analysis and in vitro microbiological evaluation of 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones as a new class of antibacterial and antifungal agents

  摘要：

  In the present work, a new series of bis hybrid heterocycle comprising both piperidine and thiohydantoin nuclei together namely 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones 46-60 was synthesized by the treatment of the respective thiosemicarbazones 31-45 with chloroethyl acetate and anhydrous sodium acetate in refluxing ethanol for 4 h and were characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR (H-1, D2O exchanged H-1 and C-13), two dimensional HOMOCOSY and NOESY spectroscopic data. In addition, the title compounds were screened for their antimicrobial activities against a spectrum of clinically isolated microbial organisms. Compounds 47-50, 52-55 and 57-60 with fluoro, chloro, methoxy or methyl functions at the para position of phenyl rings attached to C-2 and C-6 carbons of piperidine moiety along with and without methyl substituent at position C-3 of the piperidine ring exerted potent biological activities againstStaphylococcus aureus, beta-Hemolytic streptococcus, Vibrio cholerae, Escherichia coli, Pseudomonas aeruginosa, Aspergillus flavus, Candida albicans, Candida 6 and Candida 51 at a minimum inhibitory concentration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.074

文献信息

• Synthesis of thiazole-based substituted piperidinone oximes: Profiling of antioxidant and antimicrobial activity
  作者：Salakatte Thammaiah Harini、Honnaiah Vijay Kumar、Javarappa Rangaswamy、Nagaraja Naik

  DOI：10.1134/s1068162017020042

  日期：2017.3

  The synthesis of novel thiazole-based piperidinone oximes and screening of their antioxidant and antimicrobial activity are described. The obtained results revealed that the electronic effects of active substituents at C-4 terminals of phenyl rings on either side of piperidinone skeleton, as well as at 2-hydrazinyl thiazole, played a major role in development of antioxidant and antimicrobial activity

  描述了新型噻唑基哌啶酮肟的合成及其抗氧化和抗菌活性的筛选。获得的结果表明，哌啶酮骨架两侧苯环 C-4 末端的活性取代基以及 2-肼基噻唑的电子效应在抗氧化和抗菌活性的发展中起主要作用。抗氧化活性似乎也基于噻唑环的自由基消散能力。噻唑中硫的亲核特性和哌啶酮骨架的亲脂性极大地影响了观察到的噻唑基哌啶酮肟的抗菌活性。在合成的化合物中, 2,
• Synthesis and Biological Evaluation of Novel Benzimidazol/Benzoxazolylethoxypiperidone Oximes
  作者：Srinivasan Balasubramanian、Gopalakrishnan Aridoss、Paramasivam Parthiban、Chennan Ramalingan、Senthamaraikannan Kabilan

  DOI：10.1248/bpb.29.125

  日期：——

  Some novel benzimidazol/benzoxazolylethoxypiperidone oximes were synthesized and their antibacterial activity against Staphylococcus aureus (NCIM-2492), Bacillus subtilis (NCIM-2439), Escherichia coli (NCIM-2345) and Pseudomonas aeruginosa (NCIM-2035) and antifungal activity against Candida albicans (NCIM-C27), Candida-6 (NCIM-C27), Candida-51 (NCIM-C27), Aspergillus niger (NCIM-590) and Aspergillus flavus (NCIM-539) have been evaluated. Compounds 26 and 27 exerted potent in vitro antibacterial activity against Bacillus subtilis, Escherichia coli and Staphylococcus aureus while compounds 26, 29 and 30 exhibited potent in vitro antifungal activity against Candida albicans, Candida-51, and Aspergillus niger.

  合成了一些新型的苯并咪唑/苯并氧杂唑乙氧基哌啶酮肟，并评估了它们对金黄色葡萄球菌（NCIM-2492）、枯草芽孢杆菌（NCIM-2439）、大肠杆菌（NCIM-2345）和铜绿假单胞菌（NCIM-2035）的抗菌活性，以及对白色念珠菌（NCIM-C27）、Candida-6（NCIM-C27）、Candida-51（NCIM-C27）、黑曲霉（NCIM-590）和黄曲霉（NCIM-539）的抗真菌活性。化合物26和27对枯草芽孢杆菌、大肠杆菌和金黄色葡萄球菌表现出强大的体外抗菌活性，而化合物26、29和30则对白色念珠菌、Candida-51和黑曲霉展示了强大的体外抗真菌活性。
• SYNTHESIS OF SOME BENZOXAZOLYLETHOXYPIPERIDONES
  作者：C. Ramalingan、S. Balasubramanian、S. Kabilan

  DOI：10.1515/hc.2004.10.2-3.187

  日期：2004.1

  condensation with o-aminophenol afforded l-[2-(benzoxazol-2-yl)ethoxy]-2,6diarylpiperidin-4-ones. 2,6-Disubstituted piperidines form a biologically important class of compounds due to their diverse pharmacological activities such as sedative, hypotensive, stimulant and depressant activities etc. and their presence in a variety of alkaloids(l-4). Benzoxazole and its derivatives have been reported to be antibacterial

  l-Hydroxy-2,6-diarylpiperidin-4-ones 由相应的 2,6-diarylpiperidin-4-ones 在氰乙基化后与邻氨基苯酚缩合得到 l-[2-(benzoxazol-2-yl)ethoxy] -2,6diarylpiperidin-4-ones。由于 2,6-二取代哌啶具有多种药理活性，例如镇静、降压、兴奋和镇静等活性，并且存在于多种生物碱 (l-4) 中，因此它们形成了一类具有重要生物学意义的化合物。据报道，苯并恶唑及其衍生物具有抗菌 (5)、镇痛 (6)、抗真菌 (7)、活性等。苯并恶唑核的抗炎活性因新抗炎药苯并恶洛芬 (8) 的出现而得到充分证实。来自恶唑的药物包括抗癫痫药物曲美二酮和对美二酮 (9)，镇静和肌肉松弛剂苯并恶唑胺 (9) 和呋喃唑酮 (10)，可有效对抗多种肠道感染。这些观察结果促使我们合成了一个系统，该系统将生物不稳定的哌啶和
• Design, Synthesis and In Vitro Antimalarial Evaluation of New Quinolinylhydrazone Derivatives
  作者：Le Thi Thuy、Hoang Xuan Tien、Vu Dinh Hoang、Tran Khac Vu

  DOI：10.2174/157018012799079815

  日期：2012.2.1

  A series of novel quinolinylhydrazones (5a-f) was synthesized by the condensation reaction of 2,6-diarylsubstituted piperidin-4-ones (4a-f) with 7-chloro-4-hydrazinoquinoline (2). Novel quinolinylhydrazones containing Shiff bases 8a-f and 11a-f were obtained via the condensation of Shiff bases 7a-f and 10a-f with 7-chloro-4-hydrazinoquinoline. These synthesized hydrazones were screened for their in vitro antimalarial activities to chloroquine - sensitive (T96) and chloroquine – resistant (K1) strains of P.falciparum. Among the synthesized compounds, 11a exhibited strong antimalarial activity at IC50 of 103.4 ng/mL and 18.76 ng/mL to both strains of P.falciparum, respectively.

  合成了一系列新型喹啉乙肼酮（5a-f），通过2,6-二芳基取代的哌啶-4-酮（4a-f）与7-氯-4-羟基喹啉（2）的缩合反应获得。通过7a-f和10a-f的Schiff碱与7-氯-4-羟基喹啉的缩合，获得了包含Schiff碱的新型喹啉乙肼酮8a-f和11a-f。这些合成的乙肼酮对氯喹敏感（T96）和氯喹耐药（K1）型恶性疟原虫（P.falciparum）进行了体外抗疟活性筛选。在合成的化合物中，11a对两种P.falciparum株表现出强的抗疟活性，其IC50分别为103.4 ng/mL和18.76 ng/mL。
• Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles
  作者：Paramasivam Parthiban、Gopalakrishnan Aridoss、Paramasivam Rathika、Venkatachalam Ramkumar、Senthamaraikannan Kabilan

  DOI：10.1016/j.bmcl.2009.04.038

  日期：2009.6

  Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.