Syntheses of 4-(3,5-Bisphenylmethylene-4-oxo-piperidin-1-yl)-4-oxo-but-2Z-enoic Acid Arylamides as Candidate Cytotoxic Agents

References

• Dimmock , J.R. , Arora , V.K. , Quail , J.W. , Pugazhenthi , U. , Allen , T.M. , Kao , G.Y. and De Clercq , E. 1994 . Cytotoxic evaluation of some 3,5-diarylidene-4-piperidones and various related quaternary ammonium compounds and analogs . J. Pharm. Sci. , 83 ( 8 ) : 1124 – 1130 .
   PubMed Web of Science ®Google Scholar
• Dimmock , J.R. , Arora , V.K. , Chen , M. , Allen , T.M. and Kao , G.Y. 1994 . Cytotoxic evaluation of some N-acyl and N-acyloxy analogues of 3,5-bis(arylidene)-4-piperidones . Drug Des. Discovery , 12 ( 1 ) : 19 – 28 .
   PubMedGoogle Scholar
• Dimmock , J.R. , Padmanilayam , M.P. , Puthucode , R.N. , Nazarali , A.J. , Motaganhalli , N.L. , Zello , G.A. , Quail , J.W. , Oloo , E.O. , Kraatz , H.B. , Prisciak , J.S. , Allen , T.M. , Santos , C.L. , Balzarini , J. , De Clercq , E. and Manavathu , E.K. 2001 . A conformational and structure-activity relationship study of cytotoxic 3,5-bis(arylidene)-4-piperidones and related N-acryloyl analogues . J. Med. Chem. , 44 ( 4 ) : 586 – 593 .
   PubMed Web of Science ®Google Scholar
• Dimmock , J.R. , Arora , V.K. , Duffy , M.J. , Reid , R.S. , Allen , T.M. and Kao , G.Y. 1992 . Evaluation of some N-acyl analogues of 3,5-bis(arylidene)-4-piperidones for cytotoxic activity . Drug Des. Discovery , 8 ( 4 ) : 291 – 299 .
   PubMedGoogle Scholar
• Baluja , G. , Municio , A.M. and Vega , S. 1964 . Reactivity of some α,β-unsaturated ketones towards sulfhydryl compounds and their antifungal activity . Chem. Ind. (London) , 50 : 2053 – 2054 .
   Google Scholar
• Dimmock , J.R. , Erciyas , E. , Raghavan , S.K. and Kirkpatrick , D.L. 1990 . Evaluation of the cytotoxicity of some Mannich bases of acetophenone against the EMT6 tumor . Pharmazie , 45 ( 10 ) : 755 – 757 .
   PubMed Web of Science ®Google Scholar
• Dimmock , J.R. , Raghavan , S.K. , Logan , B.M. and Bigam , G.E. 1983 . Antileukemic evaluation of some Mannich bases derived from 2-arylidene-1,3-diketones . Eur. J. Med. Chem. , 18 ( 3 ) : 248 – 254 .
   Web of Science ®Google Scholar
• Mutus , B. , Wagner , J.D. , Talpas , C.J. , Dimmock , J.R. , Phillips , O.A. and Reid , R.S. 1989 . 1-p-Chlorophenyl-4,4-dimethyl-5-diethylamino-1-penten-3-one hydrobromide, a sulfhydryl-specific compound which reacts irreversibly with protein thiols but reversibly with small molecular weight thiols . Anal. Biochem. , 177 ( 2 ) : 237 – 243 .
   PubMed Web of Science ®Google Scholar
• Perrin , D.D. , Dempsey , B. and Serjeant , E.P. 1981 . pKa Prediction of Organic Acids and Bases p. 123 London : Chapman and Hall .
   Google Scholar
• Barakat , M.Z. , Shehab , S.K. and El-Sadr , M.M. 1957 . Some maleimides, maleamic acids and phthalimides . J. Chem. Soc. , : 4133 – 4135 .
   Web of Science ®Google Scholar
• Arora , V.K. 1991 . Synthesis of thiol-depleting agents with selective toxicity to malignant cells Saskatoon : University of Saskatchewan . PhD Thesis
   Google Scholar
• Canoira , L. and Rodriguez , J.G. 1988 . Synthesis and isomerization of the N,N-dimethylamides of the 2′-chloromaleanilic acids . J. Chem. Res. Miniprint , 11 : 2836 – 2855 .
   Google Scholar
• Machida , M. , Machida , M.I. and Kanaoka , Y. 1977 . Hydrolysis of N-substituted maleamides: Stability of fluorescence thiol reagents in aqueous media . Chem. Pharm. Bull. , 25 ( 10 ) : 2739 – 2743 .
   Web of Science ®Google Scholar
• Roth , M. 1979 . Spiro-β-lactams from [2+2] cycloaddition of ketenes to iminolactones . Helv. Chim. Acta , 62 ( 6 ) : 1966 – 1977 .
   Web of Science ®Google Scholar
• Capraro , H.G. , Winkler , T. and Martin , P. 1983 . [2+2] Cycloaddition of maleic isoimides with ketenes and reaction of spiro-β-lactams to muconic and tetramic acids . Helv. Chim. Acta. , 66 ( 1 ) : 362 – 378 .
   Web of Science ®Google Scholar
• Roderick , W.R. and Bhatia , P.L. 1963 . Action of trifluoroacetic anhydride on N-substituted amic acids . J. Org. Chem. , 28 ( 8 ) : 2018 – 2024 .
   Web of Science ®Google Scholar
• Canoira , L. and Rodriguez , J.G. 1985 . Synthesis of oxindole derivatives from N-alkenyl-o-chloroamines with zero-valent Nickel complex . J. Heterocyclic Chem. , 22 ( 6 ) : 1511 – 1518 .
   Web of Science ®Google Scholar
• Silverstein , R.M. , Bassler , G.C. and Morrill , T.C. 1991 . “ Proton spin-coupling constants ” . In Spectrometric Identification of Organic Compounds, , 5th Edition p. 221 New York : John Wiley & Sons, Inc. .
   Google Scholar
• “ CS Chem3D Pro® Computational Chemistry Software ” . Cambridge, MA 02140–2317, , USA : CambridgeSoft Corporation . 100 Cambridge Park Drive
   Google Scholar
• Siegel , M. and Pressman , D. 1954 . The reactions of antiserum homologous to the p-azomaleanilate and p-azofumaranilate ion groups . J. Am. Chem. Soc. , 76 : 2863 – 2866 .
   Web of Science ®Google Scholar
• Casy , A.F. , Harper , N.J. and Dimmock , J.R. 1964 . Tertiary alcohols and related compounds from 2-dimethylaminomethylcyclohexanone . J. Chem. Soc. , Oct : 3635 – 3638 .
   Web of Science ®Google Scholar
• Dimmock , J.R. , Phillips , O.A. , Wonko , S.L. , Hickie , R.A. , Tuer , T.G. , Ambrose , S.J. , Reid , R.S. , Mutus , B. and Talpas , C.J. 1989 . Evaluation of some Mannich bases of conjugated styryl ketones and related compounds versus the WiDr colon cancer in vitro . Eur. J. Med. Chem. , 24 ( 3 ) : 217 – 226 .
   Web of Science ®Google Scholar
• Albert , A. and Serjeant , E.P. 1984 . The Determination of Ionization Constants, A Laboratory Manual. , 3rd Ed. p. 151 London : Chapman and Hall .
   Google Scholar