475474-45-4

Upstream product

• 475474-46-5 C₁₉H₂₀F₂N₄S 
• 79-04-9 chloroacetyl chloride 
• 459-57-4 4-fluorobenzaldehyde 
• 78-93-3 butanone 

Downstream Products

• 1138774-90-9 C₂₀H₁₈ClF₂NO₂ 
• 1282624-13-8 1-[2-(4-ethoxycarbonylpiperazin-1-yl)acetyl]-3-methyl-2,6-bis(p-fluorophenyl)piperidin-4-one 
• 1276544-37-6 3-(2,6-bis(4-fluorophenyl)-3-methylpiperidin-4-ylideneamino)-2-thioxoimidazolidin-4-one 
• 475474-46-5 2,6-bis(4-fluorophenyl)-3-methyl-4-piperidone thiosemicarbazide 

Relevant academic research and scientific papers

Synthesis, characterization, crystal structure, in-vitro antimicrobial evaluation and molecular docking studies of 1-(furan-2-carbonyl)-3-alkyl-2,6-diphenylpiperidin-4-one derivatives

A new class of various furoyl derivatives of 2,6-disubstituted piperidin-4-ones were synthesized and characterized by FTIR, NMR, mass and single crystal X-ray diffraction methods. The synthesized compounds were subjected to in-vitro antibacterial and antifungal activities against pathogenic microbial strains. The results pointed out that compounds 11, 12 & 14 displayed pronounced activity towards gram positive bacteria, whereas the compounds 9, 13 & 14 showed a superior inhibition activity against gram negative bacteria. The compound 9 showed a moderate activity towards the fungi. In addition, molecular docking experiments were also carried out.

Synthesis, stereochemical and biological studies of some N-cyclohexylcarbamoyl -2,6-diarylpiperidin-4-ones

A series of N-cyclohexylcarbamoylpiperidin-4-ones were synthesized by the addition reaction of corresponding piperidin-4-ones with cyclohexylisocyanate in benzene. The structure and stereochemistry of the synthesized N-cyclohexylcarbamoyl -2, 6-diarylpiperidin-4-ones, were established on the basis of their analytical and spectral data (IR, 1H and 13C NMR). 2D NMR spectra (HOMOCOSY, HSQC, HMBC and NOESY) were also recorded to analyze the stereochemistry. In the IR spectra of synthesized compounds, the characteristic absorptions due to ring and amide carbonyl functionalities were observed which evidences the formation of N-cyclohexylcarbamoyl-2, 6-diarylpiperidin-4-ones. NMR spectral results are in line with the proposed structure of the compounds synthesized. Conformational analysis was carried out from the extracted coupling constants and NOESY spectral results. The synthesized compounds were evaluated for their antibacterial and antifungal activities.

Stereoselective synthesis and spectral studies of some benzotriazolylacetyl hydrazones of 3–alkyl–2,6–diarylpiperidin–4–ones

An effort to include biologically potent benzotriazole nucleus into piperidine ring is achieved through hydrazone formation. The characterization of the synthesized compounds was carried out using FT-IR, 1H &13C NMR, 1H–1H COSY, 1H–13C COSY, NOESY spectral techniques and GC-Mass spectrum. The spectral assignments were done without ambiguity using 2D-NMR techniques. The conformational preference of the piperidine ring deduced from the spectral studies is ‘chair’. The diastereotopic nature of the methylene protons/methyl groups present in the molecules is revealed clearly in their spectral pattern observed.

Chemoselective synthesis and spectral studies of N-thiocyanatoacetyl derivatives of 3-alkyl-2,6-diarylpiperidin-4-ones

A series of N–thiocyanatoacetyl derivatives of 3–alkyl–2,6–diarylpiperidin–4–ones has been synthesized by the reaction between the N–chloroacetyl derivatives of the respective piperidin–4–ones and the ambident thiocyanate nucleophile. The synthesized compounds have been characterized through FT–IR,1H,13C,1H–1H COSY,1H–13C COSY and NOESY spectra. The spectral data reveal the conformational priority of the six-membered heterocyclic ring.

Synthesis of 4-methyl-N′-(3-alkyl-2r,6c-diarylpiperidin-4-ylidene)-1, 2,3-thiadiazole-5-carbohydrazides with antioxidant, antitumor and antimicrobial activities

The structures of the newly synthesized 4-methyl-N′-(3-alkyl-2r,6c- diarylpiperidin-4-ylidene)-1,2,3-thiadiazole-5-carbohydrazide (5a-5l) were confirmed by spectral and elemental analysis. The difference in the potency of activity against various free radicals, human cancer cells and microbial strains has been evaluated by SAR. Compounds with electron-donating methoxy (5i and 5c) and methyl (5h and 5b) substitutions at the para position of the phenyl showed excellent free radical scavenging effects. In the tested compounds, electron withdrawing fluoro (5k and 5e), chloro (5j and 5d), and bromo (5l and 5f) substitution at the para position of the phenyl ring attached to C-2 and C-6 carbons of the piperidine moiety outperformed cytotoxic and antimicrobial activities. Our findings suggest that the antioxidant, anti-tumor and anti-microbial activities of compounds 5a-5l create promising leads for the development of potent anti-tumor and anti-microbial agents. This journal is the Partner Organisations 2014.

Stereoselective synthesis, spectral and antimicrobial studies of some cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones

A series of novel cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones were synthesized stereoselectively and characterized by IR, Mass, 1H NMR, 13C NMR, 1H-1H COSY and 1H-13C COSY spectra. The stereochemistry of the synthesized compounds was established using NMR spectra. Antimicrobial screening of the synthesized compounds revealed their antibacterial and antifungal potencies. Growth inhibition of Enterobacter Aerogenes by compound 15 was found to be superior to the standard drug.

Synthesis, stereochemical, structural and biological studies of some 2,6-diarylpiperidin-4-one N(40)-cyclohexyl thiosemicarbazones

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.

Synthesis, NMR spectral studies and antimicrobial evaluation of some 2-(benzothiazol-2-yl)-1-(alkyl-2r,6c-diarylpiperidin-4-ylidine)hydrazine derivatives

Substituted 2-(benzothiazol-2-yl)-1-(alkyl-2,6-diarylpiperidin-4-ylidine) hydrazines 10-17 were synthesized by the condensation of different 2r,6c-diarylpiperidin-4-ones 1-8 with 2-hydrazinobenzothiazole 9. All the synthesized compounds were investigated in solution and in the solid state by IR, 1H, 13C and 2D NMR spectral techniques. The structure-activity relationships were studied by the screening of the antimicrobial activity over a representative panel of bacterial and fungal strains using two-fold serial dilution method.

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

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.

A facile microwave assisted green chemical synthesis of novel piperidino 2-thioxoimidazolidin-4-ones and their in vitro microbiological evaluation

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.