1023-20-7Relevant articles and documents
Synthesis of mannich bases by two different methods and evaluation of their acetylcholine esterase and carbonic anhydrase inhibitory activities
Gul, Halise I.,Demirtas, Alkan,Ucar, Gokbay,Taslimi, Parham,Gulcin, Ilhami
, p. 573 - 580 (2017/05/31)
Background: Mannich bases are an important compounds in medicinal chemistry. They have wide range of biological activities including carbonic anhydrase (CA) inhibitory and acetylcholine esterase inhibitory (AChE) activities. Objective: It was aimed to synthesize Mannich bases, 1-aryl-3-(morpholin-4-yl/piperidin-1-yl)-1- propanone hydrochloride, by microwave irradiation and conventional heating methods to compare the methods in terms of reaction times and yields and to investigate their inhibitory effects on AChE enzyme and CA isoenzymes. Method: Mannich bases were synthesized using conventional heating and microwave irradiation methods under different reaction conditions. Inhibitory effects of the compounds on CA isoenzymes and AChE were evaluated according to literature procedure. Results: IC50 and Ki values of the compounds were evaluated against hCA I, II and AChE. The compounds had more potent or equal Ki values with the references used. Conclusion: This study makes an important contribution to the Mannich base library in terms of synthetic strategy. According to IC50 or Ki values the compounds 6 in Series A with morpholine and and 15 in Series B with piperidine towards both hCA I and/or II isoenzymes and the compounds 4 in Series A and 11, 13, 14, 15, 16, and 18 in Series B towards AChE seemed the leader compounds of the study.
Synthesis of new N,N′-bis[1-aryl-3-(piperidine-1-yl)propylidene] hydrazine dihydrochlorides and evaluation of their cytotoxicity against human hepatoma and breast cancer cells
Kucukoglu, Kaan,Gul, H. Inci,Cetin-Atalay, Rengul,Baratli, Yosra,Charles, Anne-Laure,Sukuroglu, Murat,Gul, Mustafa,Geny, Bernard
, p. 420 - 426 (2014/06/09)
N,N0-Bis[1-aryl-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides were synthesized by the reaction of 2 mols of 1-aryl-3-(piperidine-1-yl)-1- propanone hydrochlorides with 1 mol of hydrazine hydrate. Aryl part was C 6H5 (P1), 4-CH3C6H4 (P2), 4-CH3OC6H4 (P3), 4-HOC6H 4 (P4), 4-ClC6H4 (P5), 3-CH3OC 6H4 (P6), 4-FC6H4 (P7) and 4-BrC6H4 (P8). Except P1, all compounds were reported for the first time. The chemical structures were confirmed by UV, 1H NMR, 13C NMR and HRMS spectra. P1, P2, P7 and P8 against human hepatoma (Huh7) cells and P1, P2, P4, P5, P6, P7 and P8 against breast cancer (T47D) cells have shown cytotoxicity. P1, P2 and P7 had more potent cytotoxicity against Huh7 cells than the reference compound 5-FU, whereas only P2 was more potent than the 5-FU against T47D cells. Representative compound P7 inhibited the mitochondrial respiration at 144, 264 and 424 mM concentrations dose-dependantly in liver homogenates. The results suggest that P1, P2, P7 and P8 may serve as model compounds for further synthetic studies.
Synthesis of hypolipidemic evaluation of β-alkylaminopropiophenone and β-alkylaminopropio-2'-naphthone derivatives in rodents
Huang,Hall
, p. 199 - 206 (2007/10/03)
A series of β-alkylamino-(4'-alkyl)-propiophenone or β-alkylamino(7'-methyl)-propio-2'-naphthone derivatives were prepared and found to have hypolipidemic activity by lowering both serum cholesterol and triglyceride levels in rodents. The electron donating substituent at the para position of the phenyl ring seems to decrease the hypolipidemic activity when compared to non-substituted or electron withdrawing group substituted analogs as investigated previously in this laboratory. In comparison with lovastatin or clofibrate, most of these analogs showed similar or higher activity in lowering both serum cholesterol or triglyceride levels. β-Pyrrolidino-(4'-methyl)-propiophenone (1) demonstrated the best activity after 16 d, i.p. administration in mice at 8 mg/kg/d. Further detailed studies in rats indicated that β-pyrrolidino-(4'-methyl)-propiophenone also showed decreased serum cholesterol and triglyceride levels with increased HDL-cholesterol and triglyceride levels after 14 d. In hyperlipidemic mice and rats, this compound was observed to be effective in lowering serum lipid levels as well as tissue lipid levels. The activities of hepatic acetyl CoA synthetase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase were moderately inhibited by β-pyrrolidino-(4'-methyl)-propiophenone.
