64912-40-9Relevant academic research and scientific papers
Synthesis, structure prediction, pharmacokinetic properties, molecular docking and antitumor activities of some novel thiazinone derivatives
Anand, Selvam Athavan Alias,Loganathan, Chandrasekaran,Thomas, Nisha Susan,Saravanan, Kuppusamy,Alphonsa, Antony Therasa,Kabilan, Senthamaraikannan
, p. 7120 - 7129 (2015)
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
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.
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.
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.
Stereoselective synthesis, spectral and antimicrobial studies of some cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones
Velayutham Pillai,Rajeswari,Vidhyasagar
, p. 174 - 182 (2015/02/19)
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, spectral and antimicrobial evaluation of some novel 1-methyl-3-alkyl-2,6-diphenylpiperidin-4-one oxime carbonates
Sivakumar, Rajamanickam,Gokula Krishnan, Kannan,Thanikachalam, Venugopal
, p. 3195 - 3199 (2013/06/27)
Synthesis of some novel biologically active piperidin-4-one oxime carbonates from 1-methyl-3alkyl-2,6-diphenylpiperidin-4-one oximes and substituted chloroformates was carried out in the presence of potassium carbonate as base and tetrabutylammonium bromide (TBAB) as catalyst. The newly synthesized compounds were characterized by IR, 1H, 13C NMR and LC-mass spectra. Based on the 1H NMR analysis, all the compounds were found to adopt normal chair conformation with equatorial orientation of all the substituents. For all the synthesized compounds (5a-5l) antimicrobial activity has been tested against bacterial and fungal strains using Streptomycin and Amphotericin B as standards.
Oxidative deoximation of N-methyl-2,6-diphenyl piperidin-4-one oxime and its 3-alkyl derivatives by acid dichromate
Santhi
scheme or table, p. 2529 - 2532 (2012/08/27)
Kinetics of oxidation of N-methyl-2,6-diphenyl piperidin-4-one and its 3-alkyl substituted derivatives by acid dichromate has been studied in aqueous acetic acid medium. The oxidation is first order with respect to [oxidant] and [substrate]. The reactions are acid catalyzed. Ionic strength has no appreciable effect on the reaction rate. The reaction rate decreases with decrease in the dielectric strength of the medium indicating a polar mechanism. The reactions followed at four different temperatures and the activation parameters computed. Based on the results obtained a suitable mechanism is proposed. The reactivity sequence is found to be 1,3,5-trimethyl PPO > 1-methyl PPO > 1,3-dimethyl PPO > 1-methyl-3-ethyl PPO > 1-methyl-3-isopropyl PPO.
Environmentally benign one-pot synthesis and antimicrobial activity of 1-methyl-2,6-diarylpiperidin-4-ones
Nithya, Pattusamy,Khan, Fazlur-Rahman Nawaz,Roopan, Selvaraj Mohana,Shankar, Uma,Jin, Jong Sung
experimental part, p. 743 - 746 (2012/04/04)
An efficient and environmentally benign one-pot method for the synthesis of 1-methyl-2,6- diarylpiperidin-4-ones using montmorillonite K-10 as a catalyst has been developed. Antimicrobial activity of the compounds has been tested against selected represen
A piperidinium triflate catalyzed Biginelli reaction
Ramalingan, Chennan,Park, Su-Jung,Lee, In-Sook,Kwak, Young-Woo
scheme or table, p. 2987 - 2994 (2010/06/19)
A piperidinium triflate, 1,1,3,5-tetramethyl-4-oxo-2,6-diphenylpiperidinium triflate, in acetonitrile efficiently catalyzes one synthetic operational construction of biopertinent hydropyrimidines from respective aldehyde, β-dicarbonyl, and urea/thiourea building blocks.
Synthesis, spectral and biological evaluation of some new thiazolidinones and thiazoles based on t-3-alkyl-r-2,c-6-diarylpiperidin-4-ones
Aridoss,Amirthaganesan,Kim,Kim,Jeong, Yeon Tae
scheme or table, p. 4199 - 4210 (2009/12/06)
A stereospecific synthesis of some thiazolidinones and thiazoles was achieved conveniently through certain α-halo keto agents and reactivity of chloroacetyl chloride was successfully enhanced by CsF-Celite + CH3COONa. NMR studies revealed that the configuration of N-N bond is found to be anti with respect to C-3 alkyl group while C{double bond, long}N bond in thiazolidinone is trans with respect to N-N bond. Antimycobacterial activity tested against Mycobacterium tuberculosis indicated that compounds 19, 20, 24, 29, 30 and 32 exhibited twofold enhanced potency than Rifampicin. Similarly, antimicrobial screening studies pointed out that compounds 21 and 28 exceptionally noticed promising activities and particularly, 21 against Staphylococcus aureus and, 24 and 32 against Rhizopus sp. exhibited onefold elevated inhibition potency whereas 21 against Klebsiella pneumoniae showed twofold improved potency than Ciprofloxacin and Amphotericin B.
