Synthesis, antitumor activity evaluation of some new N-aroyl-α,β-unsaturated piperidones with fluorescence

References

• Shintani R, Tokunaga N, Doi H, et al. A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: addition of organozinc reagents for the synthesis of 2-aryl-4-piperidones. J Am Chem Soc 2004;126:6240–1
   PubMed Web of Science ®Google Scholar
• Weintraub PM, Sabol JS, Kane JM, Borcherding DR. Recent advances in the synthesis of piperidones and piperidines. Tetrahedron 2003;59:2953–89
   Web of Science ®Google Scholar
• Dimmock JR, Ealias DW, Beazely MA, et al. Bioactivities of chalcones. Curr Med Chem 1999;6:1125–49
   PubMed Web of Science ®Google Scholar
• Feenstra RW, Long SK, vander Heijden JAM, et al. Use of compounds having combined dopamine D-5HT1A and α-adrenoreceptor agonist action for treating central nervous system disorders. US Patent 2003/0186838 A1; 2003
   Google Scholar
• Comins DL, Brooks CA, Ingalls CL. Reduction of N-acyl-2-3-dihydro-4-pyridones to N-acyl-4-piperidones using zinc and acetic acid. J Org Chem 2001;66:2181–2
   PubMed Web of Science ®Google Scholar
• Baldwin PR, Reeves AZ, Powell KR, et al. Monocarbonyl analogs of curcumin inhibit growth of antibiotic sensitive and resistant strains of mycobacterium tuberculosis. Eur J Med Chem 2015;92:693–9
   PubMed Web of Science ®Google Scholar
• Bazzaro M, Anchoori RK, Mudiam MKR, et al. α,β-Unsaturated carbonyl system of chalcone-based derivatives is responsible for broad inhibition of proteasomal activity and preferential killing of human papilloma virus (HPV) positive cervical cancer cells. J Med Chem 2011;54:449–56
   PubMed Web of Science ®Google Scholar
• Duffield KM, Jha A. 3,5-Bis(arylmethylene)-4-piperidone derivatives as novel anticancer agents. Indian J Chem 2006;45B:2313–20
   Google Scholar
• Chen G, Waxman DJ. Role of cellular glutathione and glutathione S-transferase in the expression of alkylating agent cytotoxicity in human breast cancer cells. Biochem Pharmacol 1994;47:1079–87
   PubMed Web of Science ®Google Scholar
• Tsutsui K, Komuro C, Ono K, et al. Chemosensitization by buthionine sulfoximine in vivo. Int J Radiat Oncol Biol Phys 1986;12:1183–6
   PubMed Web of Science ®Google Scholar
• Das S, Das U, Sakagami H, et al. Dimeric 3,5-bis(benzylidene)-4-piperidones: a novel cluster of tumour-selective cytotoxins possessing multidrug-resistant properties. Eur J Med Chem 2012;51:193–9
   PubMed Web of Science ®Google Scholar
• Das U, Sharma RK, Dimmock JR. 1,5-Diaryl-3-oxo-1,4-pentadienes: a case for antineoplastics with multiple targets. Curr Med Chem 2009;16:2001–20
   PubMed Web of Science ®Google Scholar
• Das S, Das U, Sakagami H, et al. Sequential cytotoxicity: a theory examined using a series of 3,5-bis(benzylidene)-1-diethylphosphono-4-oxopiperidines and related phosphonic acids. Bioorg Med Chem Lett 2010;20:6464–8
   PubMed Web of Science ®Google Scholar
• Pati HN, Das U, Quail JW, et al. Cytotoxic 3,5-bis(benzylidene)piperidin-4-ones and N-acyl analogs displaying selective toxicity for malignant cells. Eur J Med Chem 2008;43:1–7
   PubMed Web of Science ®Google Scholar
• Das U, Sakagami H, Chu Q, et al. 3,5-Bis(benzylidene)-1-[4-2-(morpholin-4-yl)ethoxyPhenylcarb-onyl]-4-piperidone hydrochloride: a lead tumor-specific cytotoxin which induces apoptosis and autophagy. Bioorg Med Chem Lett 2010;20:912–17
   PubMed Web of Science ®Google Scholar
• Nesterov VN, Timofeeva TV, Sarkisov SS, et al. 3,5-Bis[4-(diethylamino)benzylidene]-1-methyl-4-piperidone and 3,5-bis-[4-(diethyl amino)cinnamylidene]-1-methyl-4-piperidone: prospective biophotonic materials. Acta Cryst 2003;C59:o605–8
   Google Scholar
• Short KW, Kinnibrugh TL, Sammeth DM, et al. Spectroscopic, cyto-, and photo-toxicity studies of substituted piperidones: potential sensitizers for two-photon photodynamic therapy. Proc SPIE 2009;7164:716411–19
   Google Scholar
• Makarov MV, Leonova ES, Rybalkina EY, et al. Methylenebisphosphonates with dienone pharmacophore: synthesis, structure, antitumor and fluorescent properties. Arch Pharm Chem Life Sci 2012;345:349–59
   PubMed Web of Science ®Google Scholar
• Nesterov VN. 3,5-Bis(4-methoxybenzylidene)-1-methyl-4-piperidone and 3,5-bis(4-methoxybenzylidene)-1-methyl-4-oxopiperidiniumchloride: potential biophotonic materials. Acta Cryst 2004;C60:o806–9
   Google Scholar
• Jha A, Mukherjee C, Prasad AK, et al. E,E,E-1-(4-Arylamino-4-oxo-2-butenoyl)-3,5-bis(arylidene)-4-piperidones: a topographical study of some novel potent cytotoxins. Bioorg Med Chem 2007;15:5854–65
   PubMed Web of Science ®Google Scholar
• Das S, Das U, Selvakumar P, et al. 3,5-Bis(benzyli dene)-4-oxo-1-phosphonopiperidines and related diethyl esters: potent cytotoxins with multi-drug-resistance reverting properties. ChemMedChem 2009;4:1831–40
   PubMed Web of Science ®Google Scholar
• Das U, Alcorn J, Shrivastav A, et al. Design, synthesis and cytotoxic properties of novel 1-[4-(2-alkylaminoethoxy) phenylarbonyl]-3,5-bis(arylidene)-4-piperidones and related compounds. Eur J Med Chem 2007;42:71–80
   PubMed Web of Science ®Google Scholar
• Hou GG, Ma JP, Wang L, et al. Co-crystallization of oxadiazole-bridged pyridyl-N-oxide building modules with R-aromatics (R = –OH, –NH2 and –COOH). CrystEngComm 2010;12:4287–303
   Web of Science ®Google Scholar
• Hou GG, Zhao HJ, Sun JF, et al. Synthesis, structure and luminescence of co-crystals with hexagonal channels: arranging disposition and π–π interactions. CrystEngComm 2013;15:577–85
   Web of Science ®Google Scholar