Structure–activity relationship investigation of tertiary amine derivatives of cinnamic acid as acetylcholinesterase and butyrylcholinesterase inhibitors: compared with that of phenylpropionic acid, sorbic acid and hexanoic acid

References

• Zhou B, Xing CG. Diverse molecular targets for chalcones with varied bioactivities. Med Chem (Los Angeles) 2015;5:388–404.
   PubMedGoogle Scholar
• Mathew B, Mathew GE, Ucar G, et al. Monoamine oxidase inhibitory activity of methoxy-substituted chalcones. Int J Biol Macromol 2017;104:1321–9.
   PubMed Web of Science ®Google Scholar
• Cai CY, Rao L, Rao Y, et al. Analogues of xanthones–chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates. Eur J Med Chem 2017;130:51–9.
   PubMed Web of Science ®Google Scholar
• Hofmann E, Webster J, Do T, et al. Hydroxylated chalcones with dual properties: xanthine oxidase inhibitors and radical scavengers. Bioorg Med Chem 2016;24:578–87.
   PubMed Web of Science ®Google Scholar
• Kocyigit UM, Budak Y, Eligüzel F, et al. Synthesis and carbonic anhydrase inhibition of tetrabromo chalcone derivatives. Arch Pharm 2017;350:e1700198.
   Web of Science ®Google Scholar
• Singh P, Anand A, Kumar V. Recent developments in biological activities of chalcones: a mini review. Eur J Med Chem 2014;85:758–77.
   PubMed Web of Science ®Google Scholar
• Mathew B, Suresh J, Anbazghagan S, et al. Heteroaryl chalcones: mini review about their therapeutic voyage. Biomed Prev Nutr 2014;4:451–8.
   Google Scholar
• Liu HR, Huang XQ, Lou DH, et al. Synthesis and acetylcholinesterase inhibitory activity of Mannich base derivatives flavokawain B. Bioorg. Med Chem Lett 2014;24:4749–53.
   PubMed Web of Science ®Google Scholar
• Liu HR, Liu XJ, Fan HQ, et al. Design, synthesis and pharmacological evaluation of chalcone derivatives as acetylcholinesterase inhibitors. Bioorg Med Chem 2014;22:6124–33.
   PubMed Web of Science ®Google Scholar
• Liu HR, Fan HQ, Gao XH, et al. Design, synthesis and preliminary structure activity relationship investigation of nitrogen-containing chalcone derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors: a further study based on Flavokawain B Mannich base derivatives. J Enzyme Inhib Med Chem 2016;31:580–9.
   PubMed Web of Science ®Google Scholar
• Gao XH, Zhou C, Liu HR, et al. Tertiary amine derivatives of chlorochalcone as acetylcholinesterase (AChE) and buthylcholinesterase (BChE) inhibitors: the influence of chlorine, alkyl amine side chain and α,β-unsaturated ketone group. J Enzyme Inhib Med Chem 2017;32:146–52.
   PubMed Web of Science ®Google Scholar
• Liu HR, Liu LB, Gao XH, et al. Novel ferulic amide derivatives with tertiary amine side chain as acetylcholinesterase and butyrylcholinesterase inhibitors: the influence of carbon spacer length, alkylamine and aromatic group. Eur J Med Chem 2017;126:810–22.
   PubMed Web of Science ®Google Scholar
• Naczk M, Shahidi F. Extraction and analysis of phenolics in food. J Chromatogr A 2004;1054:95–111.
   PubMed Web of Science ®Google Scholar
• Letizia CS, Cocchiara J, Lapczynski A, et al. Fragrance material review on cinnamic acid. Food Chem Toxicol 2005;43:925–43.
   PubMed Web of Science ®Google Scholar
• Khan NR, Rathod VK. Enzyme catalyzed synthesis of cosmetic esters and its intensification: a review. Process Biochem 2015;50:1793–806.
   Web of Science ®Google Scholar
• Zhao JY, Song Y, Wang HJ, et al. High performance liquid chromatographic method for the determination of cinepazide maleate and its application to a pharmacokinetic study in rats. J Chromatogr B 2014;957:105–9.
   PubMed Web of Science ®Google Scholar
• Darakhshan S, Pour AB. Tranilast: a review of its therapeutic applications. Pharmacol Res 2015;91:15–28.
   PubMed Web of Science ®Google Scholar
• Xiao FL, Yan B, Chen L, et al. Review of the use of botanicals for epilepsy in complementary medical systems – traditional Chinese medicine. Epilepsy Behav 2015;52:281–9.
   PubMed Web of Science ®Google Scholar
• Shi ZH, Li NG, Shi QP, et al. Synthesis and structure–activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors. Bioorg Med Chem Lett 2013;23:1206–11.
   PubMed Web of Science ®Google Scholar
• Xu T, Sha F, Alper H. Highly ligand-controlled regioselective Pd-catalyzed aminocarbonylation of styrenes with aminophenols. J Am Chem Soc 2016;138:6629–35.
   PubMed Web of Science ®Google Scholar
• Narasimhan B, Judge V, Narang R, et al. Quantitative structure–activity relationship studies for prediction of antimicrobial activity of synthesized 2,4-hexadienoic acid derivatives. Bioorg Med Chem Lett 2007;17:5836–45.
   PubMed Web of Science ®Google Scholar
• Froyen P. Phosphorus in organic synthesis. Acyloxyphospho-nium salts as chemoselective acylating reagents. Tetrahedron Lett 1997;38:5359–62.
   Web of Science ®Google Scholar
• Krapcho J, Schwartz J. 6-(or 8)-[[(Substituted amino)alkyl] oxy(or thio)]-3,4-dihydro-4-phenyl-2(1H)-quinolinones US. Pat 1976; 3994900.
   Google Scholar
• Ellman GL, Courtney KD, Andres VJ, et al. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95.
   PubMed Web of Science ®Google Scholar
• Luo ZH, Sheng J, Sun Y, et al. Synthesis and evaluation of multi-target-directed ligands against Alzheimer’s disease based on the fusion of donepezil and ebselen. J Med Chem 2013;56:9089–99.
   PubMed Web of Science ®Google Scholar
• Alpan AS, Parlar S, Carlino L, et al. Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors. Bioorg Med Chem 2013;21:4928–37.
   PubMed Web of Science ®Google Scholar
• Yu H, Li WM, Kan KK, et al. The physicochemical properties and the in vivo AChE inhibition of two potential anti-Alzheimer agents, bis(12)-hupyridone and bis(7)-tacrine. J Pharm Biomed Anal 2008;46:75–81.
   PubMed Web of Science ®Google Scholar
• González AG, Herrador MA. Ionization constants of water insoluble arylpropionic acids in aqueous N, N -dimethylformamide mixtures from potentiometric pH-titrations. Analytica Chimica Acta 1997;356:253–8.
   Web of Science ®Google Scholar
• Glave WR, Hansch CJ. Relationship between lipophilic character and anesthetic activity. J Pharm Sci 1972;61:589–91.
   PubMed Web of Science ®Google Scholar
• Manallack DT. The pKa distribution of drugs: Application to drug discovery. Perspect Med Chem 2007;1:25–38.
   PubMedGoogle Scholar