199285-47-7Relevant academic research and scientific papers
Synthesis of thiazole-based substituted piperidinone oximes: Profiling of antioxidant and antimicrobial activity
Harini, Salakatte Thammaiah,Kumar, Honnaiah Vijay,Rangaswamy, Javarappa,Naik, Nagaraja
, p. 186 - 196 (2017/04/24)
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. Antioxidant activity seems to be based also on radical dissipating ability of the thiazole ring. The nucleophilic character of sulfur in thiazole and lipophilic nature of piperidinone skeleton substantially influenced the observed antimicrobial activity of thiazole-based piperidinone oximes. Among the synthesized compounds, 2,6-bis(4-hydroxy-3-methoxyphenyl)-1-methylpiperidin-4-one O-(2-(2-(4-hydroxy-3-methoxybenzylidene)hydrazinyl)thiazol-4-yl) oxime exhibited excellent antioxidant activity whereas compound 2,6-bis(4-chloro phenyl)-1-methylpiperidin-4-one O-(2-(2-(4-nitrobenzylidene)hydrazinyl)thiazol-4-yl)oxime emerged as an outstanding antimicrobial agent.
Novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters: Synthesis and a new insight into their antioxidant and antimicrobial potential
Harini, Salakatte Thammaiah,Kumar, Honnaiah Vijay,Peethambar, Sannenahalli Krishnegowda,Rangaswamy, Javarappa,Naik, Nagaraja
, p. 1887 - 1898 (2014/05/06)
A simple and efficient protocol for the synthesis of novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters 4(a-q) is described. Initially, p-anisaldehyde 1 was condensed (Mannich reaction) with acetone and ammonium acetate trihydrate afforded 2,6-bis(4-methoxyphenyl) piperidin-4-one 2. Then, methylation followed by oximationwith hydroxylamine hydrochloride (NH2OH?HCl) furnished a key scaffold 4. Further, to explore the enhanced biological properties of the piperidin-4-one core i.e. the key scaffold 4 was conjugated with substituted benzoyl chlorides in the presence of anhydrous K2CO3 as base to obtain novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters 4(a-q) in excellent yields. The newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and mass spectroscopic techniques, and screened for their in vitro antioxidant and antimicrobial activities. Most of the compounds exerted positive efficacy towards the biological assays performed. Among the synthesized analogues, compounds 4l and 4m exhibited promising antioxidant activity and on the other hand compounds 4b and 4d manifested persuasive antibacterial activity, whereas compound 4b displayed stupendous antifungal activity against A. flavus strain. Springer Science+Business Media 2013.
Design, synthesis and in vitro antimalarial evaluation of new quinolinylhydrazone derivatives
Thuy, Le Thi,Tien, Hoang Xuan,Hoang, Vu Dinh,Vu, Tran Khac
scheme or table, p. 163 - 168 (2012/07/17)
A series of novel quinolinylhydrazones (5a-f) was synthesized by the condensation reaction of 2,6-diaryl-substituted piperidin-4-ones (4a-f) with 7-chloro-4-hydrazinoquinoline (2). Novel quinolinylhydrazones containing Shiff bases 8a-f and 11a-f were obta
A facile microwave assisted green chemical synthesis of novel piperidino 2-thioxoimidazolidin-4-ones and their in vitro microbiological evaluation
Kanagarajan,Thanusu,Gopalakrishnan
experimental part, p. 67 - 77 (2011/10/17)
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 13C), two dimensional HOMOCOSY and NOESY spectroscopic data. All the synthesised title compounds were screened for their in vitro antibacterial and antifungal activity against clinically isolated strains namely B. subtilis, M. luteus, S. typhii, S. paratyphii B, S. felxneri, P. vulgaris, A. niger, Mucor, Rhizopus and M. gypsuem and the results were discussed.
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
Thanusu,Kanagarajan,Gopalakrishnan
scheme or table, p. 713 - 717 (2010/05/18)
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 (1H, D2O exchanged 1H and 13C), 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 against Staphylococcus aureus, β-Hemolytic streptococcus, Vibrio cholerae, Escherichia coli, Pseudomonas aeruginosa, Aspergillus flavus, Candida albicans, Candida 6 and Candida 51 at a minimum inhibitory concentration.
Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles
Parthiban, Paramasivam,Aridoss, Gopalakrishnan,Rathika, Paramasivam,Ramkumar, Venkatachalam,Kabilan, Senthamaraikannan
supporting information; experimental part, p. 2981 - 2985 (2010/03/03)
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.
Synthesis and biological evaluation of novel benzimidazol/ benzoxazolylethoxypiperidone oximes
Balasubramanian, Srinivasan,Aridoss, Gopalakrishnan,Parthiban, Paramasivam,Ramalingan, Chennan,Kabilan, Senthamaraikannan
, p. 125 - 130 (2007/10/03)
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
Synthesis and study of antibacterial and antifungal activities of novel 8-methyl-7,9-diaryl-1,2,4,8-tetraazaspiro[4.5]decan-3-thiones
Balasubramanian,Ramalingan,Aridoss,Kabilan
, p. 694 - 700 (2007/10/03)
Some novel spiropiperidinyl-1,2,4-triazolidin-3-thiones have been synthesized and studied for their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa and antifungal activity against Candida albicans, Candida-6, Candida-51, Aspergillus niger and Aspergillus flavus. Compounds 30-32 exhibited potent in vitro antibacterial activity against E. coli and P. aeruginosa whereas the same set of compounds exerted potent in vitro antifungal activity against Candida-6, A. niger and A. flavus.
Synthesis and study of antibacterial and antifungal activities of novel 1-[2-(benzoxazol-2-yl)ethoxy]- 2,6-diarylpiperidin-4-ones
Ramalingan,Balasubramanian,Kabilan,Vasudevan
, p. 527 - 533 (2007/10/03)
Some novel benzoxazolylethoxypiperidones have been synthesized and their antibacterial activity against streptococcus faecalis, bacillus subtilis, escherichia coli, staphylococcus aureus aand pseudomonas aeruginosa and antifungal activity against Candida-6, Candida albicans, Aspergillus niger, Candida-51 and Aspergillus flavus were evaluated. Compounds 37, 38 and 39 exerted potent in vitro antibacterial activity against Streptococcus faecalis while compounds 40 and 41 exhibited potent in vitro antifungal activity against Candida-51.
Synthesis and microbiological evaluation of novel [N-acetyl-2,6- diarylpiperidin-4-yl]-5-spiro-4-acetyl-2-(acetylamino)-Δ2-1,3, 4-thiadiazolines
Balasubramanian,Ramalingan,Aridoss,Parthiban,Kabilan
, p. 297 - 311 (2007/10/03)
Some novel spiropiperidinyl thiadiazolines have been synthesized and their bacterial activity against Streptococcus faecalis, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Klepsiella pneumoniae and antifungal activity against Cryptococcus neoformans, Candida-6, Candida-51, Aspergillus niger and Aspergillus flavus were evaluated. Compound 23 exhibited potent antibacterial activity in vitro against Klepsiella pneumoniae while compound 24 exerted potent antifungal activity in vitro against Cryptococcus neoformans. Birkhaeuser Boston 2004.
