68226-06-2Relevant academic research and scientific papers
Cross-linked polystyrene/titanium tetrachloride as a tightly bound complex catalyzed the modified Mannich reaction for the synthesis of piperidin-4-ones
Rahmatpour, Ali,Emen, Reza,Amini, Ghazal
, p. 24 - 33 (2019)
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.
Synthesis, characterization and antitumor activities of some novel thiazinones and thiosemicarbazones derivatives
Anand, Selvam Athavan Alias,George, Kiran,Thomas, Nisha Susan,Kabilan, Senthamaraikannan
supporting information, p. 821 - 829 (2020/05/22)
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.
Design, synthesis, molecular docking and antimicrobial evaluation of some tosyl carbamate derivatives
Kalaivani, Panneerselvam,Arikrishnan, Jayaraman,Gopalakrishnan, Mannuthusamy
, p. 783 - 788 (2020/03/24)
A series of tosyl carbamates have been synthesized and screened for their antibacterial and antifungal activities. All the synthesized compounds were characterized by spectral techniques (IR, 1H, 13C NMR and mass) and elemental analysis. in silico Molecular docking method was performed to study their antimicrobial activity against the target protein 1T9U. Compound 27 showed good antibacterial activity against Gram-positive and Gram-negative bacterial strains and compound 19 showed good antifungal activity. Molecular docking results revealed that the compound 19 exhibits minimum CDOCKER energy. Tosyl carbamate derivatives having good antimicrobial activities compared to that standard and all the synthesized compounds exhibits moderate CDOCKER scores.
Design, Synthesis, Characterization, Molecular docking, ADME Properties and In Vivo antipsychotic activity of aripiprazole related drugs candidates
Sekar, Selvarasu,Pazhamalai, Srinivasan,Ariharasivakumar, Ganesan,Gopalakrishnan, Mannathusamy
, p. 1073 - 1085 (2017/09/12)
Background: A series of newly synthesized compounds structurally related to Aripiprazole and Brexpiprazole, atypical antipsychotic and antidepressant used clinically for the treatment of schizophrenia, depression and bipolar disorder have been prepared and characterized by Elemental analysis, FT-IR, 1H NMR, 13C NMR, HSQC (2D NMR) and Mass spectrometry. All the compounds have been docked against, human A2A Adenosine receptor, human β2-Adrenergic G-Protein Coupled Receptor (GPCR) and ADME properties ware also evaluated. Objective: We focused on screening the neuroleptic activity of the synthesized drug molecules with different anti-psychotic animal models. Methods: All the drug molecules (10mg/kg) and also standard drug Aripiprazole (5mg/kg) were administered to their individual groups with 8 different animal models. Docking studies were carried out by Schrodinger 9.5 software to predict the antipsychotic activity and the pharmacokinetic properties were subjected to QIKPROP3.7 (Qikprop) module of Schr?dinger software to determine ADME property. Results: Both the receptor and ligand interaction shows an excellent dock score. ADME properties were also evaluated in the desirable range; finally these compounds have orally drug-likeness property. The results basically pointed out the fact that mutually the test molecules and control group may have the property to improve the positive symptoms of schizophrenia by reducing the dopamine levels of dopaminergic neurons of the brain. Conclusion: Docked against the protein to determine the Binding Energy, Glides core, Hydrogen bond, Total Intermolecular Energy and Interacting residues. ADME properties have been determined and obey the Lipinski's rule of five for drug likeness property. The synthesized compounds are used against Aripiprazole as a standard drug. The result has shown a promising effect in reducing the positive symptoms of psychosis in rats by sinking the dopamine levels in the frontal cortical region of the brain.
Stereoselective synthesis and spectral studies of some benzotriazolylacetyl hydrazones of 3–alkyl–2,6–diarylpiperidin–4–ones
Pillai, M. Velayutham,Rajeswari,Kumar, C. Udhaya,Krishnan, K. Gokula,Mahendran,Ramalingan,Nagarajan,Vidhyasagar
, p. 558 - 565 (2017/09/19)
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.
Microwave assisted deprotection of heterocyclic semicarbazones by quinolinium flurochromate
Vimala,Santhi,Anusha
, p. 2296 - 2298 (2017/10/05)
The regeneration of semicarbazone from 2,6-diphenyl piperidine-4-one semicarbazone (PPS) and its alkyl substituted derivatives (3, 3 and 5th position) by quinolinium flurochromate (QFC) under microwave irradiation in the presence of montmorillonite K10 clay leads to the formation of ketone in a good yield.
Regeneration of carbonyl compounds by deoximation of piperidine-4-one oximes with quinolinium flurochromate in presence of montmorillonite K10 clay
Vimala,Lingeswari
, p. 2485 - 2487 (2017/10/31)
The regeneration of oximes from 2,6-diphenyl piperidine-4-one oximes (PPO) and its alkyl substituted derivatives (3-alkyl PPO and 3,5- dimethyl PPO) by quinolinium flurochromate under microwave irradiation in the presence of montmorillonite K10 clay leads to the formation of ketone in a good yield.
Synthesis, spectral and structural studies of alkyl 2-(3-alkyl-2,6-diarylpiperidin-4-ylidene)hydrazinecarboxylate derivatives: Crystal and molecular structure of methyl 2-(3-methyl-2,6-diphenylpiperidin-4-ylidene)hydrazinecarboxylate
Udhaya Kumar,Sethukumar,Velayutham Pillai,Arul Prakasam,Ramalingan,Vidhyasagar
, p. 45 - 52 (2016/02/18)
An efficient synthetic route with good overall yields to synthesize alkyl 2-(3-alkyl-2,6-diarylpiperidin-4-ylidene)hydrazinecarboxylates (7-14) is reported. All the synthesized compounds were characterized by their analytical and spectral (IR, 1H, 13C and 2D NMR) data. Single crystal X-ray structural analysis of compound 7, evidences that the configuration about C=N double bond is syn to C5 carbon (E-form) and exists in normal chair conformation with equatorial orientations of all the substituents.
Synthesis, conformational preferences and antimicrobial evaluation of N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones
Akila,Jeganathan,Ponnuswamy
, p. 187 - 195 (2016/06/01)
Five new N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones 11-15 have been synthesized and characterized using IR, 1H, 13C, DEPT & 2D NMR and mass spectral studies. The NMR spectral data indicate that the N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones 11-15 prefer to exist in an equilibrium between B1 and B2 conformations. Furthermore, the antibacterial and antifungal studies were carried out. The results show that the piperazinoacetyl piperidin-4-ones 11-15 exhibit good activity against the selected bacterial and fungal strains.
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
Srikanth,Sivarajan,Venkatesan,Maheshwaran,Sugumar,Rajitha,Varalakshmi,Ponnuswamy
, p. 481 - 492 (2016/07/21)
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.
