201335-53-7

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 78-93-3 butanone 
• 597577-94-1 C₁₉H₂₀Cl₂N₄S 
• 79-04-9 chloroacetyl chloride 
• 631-61-8 ammonium acetate 

Downstream Products

• 201335-60-6 C₁₉H₂₀Cl₂N₄O 
• 1002722-15-7 N-chloroacetyl-3-methyl-2,6-bis(p-chlorophenyl)piperidin-4-one 
• 1259568-36-9 C₂₅H₂₄Cl₂N₄S 

Relevant academic research and scientific papers

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.

Synthesis, characterization and antitumor activities of some novel thiazinones and thiosemicarbazones derivatives

Two series of thiazinone and thiosemicarbazone derivatives (1-12) were synthesized using 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones (ABNs) and 3–alkyl–2,6–diarylpiperidin–4–ones as the starting materials. The structures of newly synthesized compounds were established on the basis of FT–IR, NMR spectroscopy and mass spectrometry. From the spectroscopic data, we identified that the cyclization reaction of thioamide with dialkyl acetylenedicarboxylate selectively gives six membered methyl 2-(2-(2,4-disubstituted-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazinyl)-4-oxo-4H-1,3-thiazine-6-carboxylates (1-6). In order to investigate the antitumor activities of the synthesized compounds, in?vitro cytotoxicity studies were carried out using human prostate cancer cell lines. Tested compounds showed good/moderate activities against cancer cell lines and further investigation carried out by live/dead assay.

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.

One-Pot Synthesis of Substituted Piperidinones and 3,4-Dihydropyrimidinones Using a Highly Active and Recyclable Supported Ionic Liquid Phase Organocatalyst

1-Ethyl-3-methylimidazolium ethyl sulfate was synthesized and its supported ionic liquid phase form was prepared and used as an organocatalyst for the synthesis of substituted piperidinones and 3,4-dihydropyrimidinones. The ionic liquid was characterized by 1H NMR, 13C NMR, and mass spectrometry. The catalyst is novel, stable, completely heterogeneous, and recyclable for several times and can be easily recovered by filtration. It was characterized with scanning electron microscopy, transmission electron microscopy, thermogravimetric analysis, and energy-dispersive X-ray spectroscopy techniques. The workup procedures are very simple, and products were obtained in good-to-excellent yields with reasonable purities without the need for further chromatographic purification.

Anticoagulant activity and molecular docking of 7,9-bis(4-chlorophenyl)-6-methyl-1,4-dioxa-8-azaspiro[4.5]decane through target protein thrombin

The present study reported the synthesis and anticoagulant activity of spiro compounds, the potential compound was subjected to study their binding mode and interaction using bioinformatics tools. Among the five compounds tested, 7,9-bis(4-chlorophenyl)-6-methyl-1,4,8-triaza spiro[4.5]decane has prolonged activated partial thromboplastin time and prothrombin time as 22.7s and 18.5s at 25 μg mL-1, respectively. Hence, the mandatory way study was carried out for this compound by using bioinformatics method. The interaction results shows that this compound binds in the active site of the target protein thrombin which is similar to that of existing inhibitor and it may also considered as an anticoagulant drug in future.

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, structure prediction, pharmacokinetic properties, molecular docking and antitumor activities of some novel thiazinone derivatives

A novel series of thiazinone derivatives were obtained from unexpected cyclization of dimethyl acetylenedicarboxylate (DMAD) and diethyl acetylenedicarboxylate (DEAD) with corresponding 3-alkyl-2,6-diarylpiperidin-4-one thiosemicarbazones in dry methanol

Design, synthesis and cytotoxicity of novel N-benzylpiperidin-4-one oximes on human cervical cancer cells

A series of fifteen diversified N-benzylpiperidin-4-one oximes were synthesized and characterized by their NMR spectral data. Additionally, single-crystal XRD analysis was performed for the representative symmetrically and unsymmetrically substituted molecules. All the synthesized oximes from unsymmetrical ketones existed as E-isomer as witnessed by their NMR and XRD data. Among the synthesized target compounds that evaluated for their in vitro cytotoxicity against human cervical carcinoma (HeLa) cells, five compounds were potent with IC50 50 of 13.88 μM was found to be the best active compound as depicted by the microscopic analysis.

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.