- Cross-linked polystyrene/titanium tetrachloride as a tightly bound complex catalyzed the modified Mannich reaction for the synthesis of piperidin-4-ones
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Cross-linked polystyrene beads were prepared, characterized and the resulting polymer carrier was functionalized with titanium tetrachloride (TiCl4)via complexation of polystyrene with TiCl4 to afford the corresponding cross-linked polystyrene-TiCl4 stable complex (PSt/TiCl4)in an one step reaction and characterized by FT-IR, UV, TGA, DSC, XRD, SEM, BET. This tightly bound coordination complex was used as a water tolerant, heterogeneous, recoverable and reusable Lewis acid catalyst for the synthesis of substituted piperidin-4-ones via the modified Mannich multi-component condensation of ketones, aromatic aldehydes, and ammonium acetate in 1:2:1 M ratio under mild conditions. The rate of reactions was found to decrease with an increasing percentage of crosslinking and the mesh size of the copolymer beads. The catalyst is water tolerant, stable and can be easily recovered and reused at least four times without any loss of activity.
- Rahmatpour, Ali,Emen, Reza,Amini, Ghazal
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- Synthesis, spectral characterization, crystal structure and molecular docking study of 2,7-diaryl-1,4-diazepan-5-ones
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In this study, a series of variously substituted r-2,c-7-diaryl-1,4-diazepan-5-ones 9-16 have been synthesized using Schmidt rearrangement and are characterized by IR, mass and 1D & 2D NMR spectral data. The proton NMR coupling constant and estimated dihedral angles reveal that the compounds 9-16 prefer a chair conformation with equatorial orientation of alkyl and aryl groups. Single crystal X-ray structure has been solved for compounds 9 and 11 which also indicates the preference for distorted chair conformation with equatorial orientation of substituents. The compounds 9-16 have been docked with the structure of Methicillin-resistant Staphylococcus aureus (MRSA) and the results demonstrate that compound 10 is having better docking score and glide energy than others and it is comparable to co-crystal ligand. Furthermore, all the compounds have been evaluated for their antibacterial and antioxidant activities. All the compounds show moderate antibacterial activity and only 11 exhibits better activity against S. aures and Escherichia coli. The compounds 11, 13 and 14 exhibit half of the antioxidant power when compared to the BHT and the remaining compounds show moderate activity.
- Sethuvasan,Sugumar,Maheshwaran,Ponnuswamy,Ponnuswamy
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p. 188 - 199
(2016/04/04)
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- Synthesis, stereochemical, structural and biological studies of some 2,6-diarylpiperidin-4-one N(40)-cyclohexyl thiosemicarbazones
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A new series of 2,6-diarylpiperidin-4-one N(40)-cyclohexyl thiosemicarbazones (13-23) were synthesized by corresponding 2,6-diarylpiperidin-4-ones (1-11) reaction with cyclohexyl thiosemicarbazide (12). The chemical structures were confirmed by means of IR, one and two dimensional NMR, Mass spectra and single crystal X-ray diffraction analysis. Compounds 13-23, exist in chair conformation with equatorial orientation of all the substituents at piperidine ring except the methyl group at C-5 of compounds 21-23 oriented at axial disposition to stabilize the chair conformation. Single crystal X-ray structural analysis of compound 18, evidences that the configuration about C@N double bond is syn to C-5 carbon (E-form). All the synthesized compounds were screened their biological activity.
- Sethukumar,Kumar, C. Udhaya,Agilandeshwari,Prakasam, B. Arul
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p. 237 - 248
(2013/10/22)
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- Synthesis, characterization and antibacterial studies on copper(II) binuclear complexes with substituted piperidin-4-ones
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Copper(II) Chloride binuclear complexes with variously substituted 2,6-diphenly piperidin-4-ones [Cu2LCI4(H 2O)3] have been synthesized and characterized by elemental analysis, molar conductance, magnetic suscep
- Theivarasu, Chinniagounder,Sivaprakash, Krishnan
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p. 1379 - 1387
(2013/02/25)
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- Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents
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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, 1H NMR, 13C 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 μg/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. Springer Science+Business Media, LLC 2011.
- Rani, Mannangatty,Parthiban, Paramasivam,Ramachandran, Rajamanickam,Kabilan, Senthamaraikannan
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scheme or table
p. 653 - 662
(2012/08/07)
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- Spectrophotometric study of kinetics of oxidation of oximes of 3,5-dimethyl-2,6-diarylpiperidin-4-ones with quinolinium fluorochromate
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The rate of oxidation of 3,5-dimethyl-2,6-diarylpiperidin-4-one oximes with quinolinium fluorochromate (QFC) was followed in aqueous acetic acid medium. The influence of substrate, oxidant, H+ ions, ionic strength and dielectric constant on the reaction rates at varied temperature has been studied. The stoichiometry is 1:1 and the product of oxidation is the corresponding ketone. Activation parameters have been computed and a suitable mechanism has been suggested.
- Vimala,Jani Bai
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experimental part
p. 5699 - 5704
(2012/07/28)
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- Synthesis, antimicrobial evaluation and QSAR studies of novel piperidin-4-yl-5-spiro-thiadiazoline derivatives
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In an attempt to find a new class of antimicrobial agents, a series of new 1,3,4-thiadiazolines were synthesized from 2,6-diarylpiperidin-4-ones, via the corresponding 4′-phenylthiosemicarbazones. All the synthesized compounds (23-39) were virtually screened against bacterial (Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi) and fungal strains (Candida albicans, Rhizopus sp, Aspergillus niger and Aspergillus flavus) by serial dilution method. QSAR study indicated that the increase in weakly polar component of solvent accessible surface area will favour antibacterial activity while increase in polarizability and decrease in ionisation potential and hydrogen bond donor will favour antifungal activity.
- Umamatheswari, Seeman,Balaji, Bhaskar,Ramanathan, Muthiah,Kabilan, Senthamaraikannan
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scheme or table
p. 6909 - 6914
(2011/02/16)
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- Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: Antimicrobial, analgesic and antipyretic studies
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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.
- Aridoss,Parthiban,Ramachandran,Prakash,Kabilan,Jeong, Yeon Tae
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body text
p. 577 - 592
(2009/09/27)
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- Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles
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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.
- Parthiban, Paramasivam,Aridoss, Gopalakrishnan,Rathika, Paramasivam,Ramkumar, Venkatachalam,Kabilan, Senthamaraikannan
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supporting information; experimental part
p. 2981 - 2985
(2010/03/03)
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- A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives
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The raise in clinical significance of multidrug-resistant bacterial pathogens has directed us to synthesize 2,6-diarylpiperidin-4-one and Δ3-tetrahydropyridin-4-ol based benzimidazole and O-arylsulfonyl derivatives. X-ray crystal structure of t
- Aridoss, Gopalakrishnan,Amirthaganesan, Shanmugasundaram,Ashok Kumar, Nanjundan,Kim, Jong Tae,Lim, Kwon Taek,Kabilan, Senthamaraikannan,Jeong, Yeon Tae
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scheme or table
p. 6542 - 6548
(2009/09/30)
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- Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6-diarylpiperidin-4-ones
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In a search for new leads towards potent antimicrobial agents, an array of novel N-morpholinoacetyl-2,6-diarylpiperidin-4-ones has been synthesized and their in vitro antibacterial activity against Staphylococcus aureus, 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 1H and 13C NMR spectroscopic techniques. In all the cases, amide N-C{double bond, long}O group is preferentially in coplanar orientation with respect to the dynamically averaged plane of the piperidone ring. Further, all the symmetrically substituted compounds 19, 23, 24, 26 and 27 are expected to adopt half boat conformations while other compounds 20-22 and 25 adopt twist-boat conformations. Structure-activity relationship results for these nine compounds have shown that compounds 26 and 27 exerted excellent antibacterial activity against all the bacterial strains used except 27 against S. aureus. Against C. albicans and A. flavus, compound 24 recorded excellent antifungal activities while against Rhizopus sp., compound 25 showed potent activities. The obtained results may be used as key step for the building of novel chemical compounds with interesting antimicrobial profiles comparable to that of the standard drugs.
- Aridoss,Balasubramanian,Parthiban,Kabilan
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p. 851 - 860
(2008/02/12)
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- Synthesis and antimicrobial activities of N-chloroacetyl-2,6- diarylpiperidin-4-ones
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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. Birkhaeuser 2007.
- Aridoss,Balasubramanian,Parthiban,Ramachandran,Kabilan
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p. 188 - 204
(2008/09/17)
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- Synthesis and study of antibacterial and antifungal activities of novel 1-[2-(benzoxazol-2-yl)ethoxy]- 2,6-diarylpiperidin-4-ones
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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.
- Ramalingan,Balasubramanian,Kabilan,Vasudevan
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p. 527 - 533
(2007/10/03)
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- Synthesis and microbiological evaluation of benzimidazolylethoxypiperidones
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Some novel benzimidazolylethoxypiperidones were synthesized and their antibacterial activity against Streptococcus faecalis, Bacillus subtilis, Eschericia coli, Pseudomonas aeruginosa and Klepsiella pneumoniae and antifungal activity against Cryptococcus neoformans, Candida 6, Candida 51 , Aspergillus niger and Aspergillus flavus evaluated. Compounds 38 and 39 exerted potent in vitro antibacterial activity against Klepsiella pneumoniae, while, compounds 41 and 42 exhibited potent in vitro antifungal activity against Cryptococcus neoformans.
- Ramalingan,Balasubramanian,Kabilan,Vasudevan
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