Synthesis, Antitumor, and DNA Binding Behavior of Novel 4-(2-Hydroxyquinolin-3-yl)-6-Phenyl-5, 6 Dihydropyrimidin Derivatives in Aqueous Medium

REFERENCES

• Hasegawa , S. , Masunaga , K. , Muto , M. and Hanada , S. 1991 . Chem. Abstr. , JP 0232, 086 [90 32, 086], 1990; 114, 34897k
   Google Scholar
• Peacocke , A. R. 1973 . Heterocyclic Compounds: The Acridines , Edited by: Acheson , R. M. New York : Wiley Interscience .
   Google Scholar
• Ledochowski , A. 1976 . Ledakin-Anticancerous Medicine 1-Nitro-9-(3- dimethylaminopropylamino)acridine dihydrochloride monohydrate . Mater. Med. Polon. , 8 : 237 – 251 .
   PubMedGoogle Scholar
• Afonso , A. , Weinstein , J. and Gentles , M. J. 1995 . US , 5 : 382 Chem. Abstr. 5721995; 122, 213949r
   Google Scholar
• 1991 . Ukrainskii Khimicheskii Zhurrnal , Russion edition Vol. 57(12) , 1325 – 1328 .
   Google Scholar
• Ukrainets , V. , Taran , S. G. , Sidorenko , L. V. , Gorokhova , O. V. , Ogirenko , A. A. and Turov , N. I. 1996 . 4-Hydroxy-2-quinolones. 37. Simple synthesis of 1-R-2-oxo-3,4-dihydroxyquinolines . Khim.Geterotsikl. Soedin Filimonova , 8 : 1113 – 1118 .
   Google Scholar
• Petal , N. C. and Mehta , A. G. 2001 . Synthesis of bisazo acid dyes based on 4-hydroxy-1-phenylquinoline-2(1H)-one system and their dyeing performance on various fabrics . Asian J. Chem , 13 : 1385 – 1388 .
   Google Scholar
• Munawar , M. A. , Azad , M. , Siddiqu , H. L. and Nasim , H. F. 2008 . Synthesis and antimicrobial studies of some quinolinylpyrimidine derivatives . J. Chin. Chem. Soc , 55 : 394 – 400 .
   Web of Science ®Google Scholar
• Joshi , A. A. and Viswanathan , C. L. 2006 . Recent developments in antimalarial drug discovery . Anti-Infect Agent Med Chem , 5 : 105 – 122 .
   Google Scholar
• El-Sayed , O. A. , El-Baih , F. M.E. , El-Aqeel , Sh. I. , Al Bassam , B. A. and Hussein , M. E. 2002 . Novel 4-aminopyrimido[4,5-b]quinoline derivatives as potential antimicrobial agents . Boll. Chem. Farmac 141, 6 , : 461 – 465 .
   Google Scholar
• El-Sayed , O. A. , Al-Bassam , B. A. and Hussein , M. E. 2002 . Synthesis of some novel quinoline-3-carboxylic acids and pyrimidoquinoline derivatives as potential antimicrobial agents . Arch. Pharm. , 335 : 403 – 410 .
   PubMed Web of Science ®Google Scholar
• Glushkov , V. A. , Stryapunina , O. G. , Gorbunov , A. A. , Maiorova , O. A. , Slepukhin , P. A. , Ryabukhina , S. Ya. , Khorosheva , E. V. , Sokol , V. I. and Shklyaev , Y. V. 2010 . Synthesis of 1-substituted 2-azaspiro[4.5]deca-6, 9-diene-8-ones and 2-azaspiro[4.5]deca-1,6,9-triene-8-ones by a three-component condensation of 1,2,3-, 1,2,4- or 1,3,5-trimethoxybenzene with isobutyric aldehyde and nitriles . Tetrahedron , 66 : 721 – 729 .
   Web of Science ®Google Scholar
• El-Sayed , O. A. , Al-Turki , T. M. , Al-Daffiri , H. M. , Al-Bassam , B. A. and Hussein , M. E. 2004 . Pyrimidoquinoline derivatives as anti-inflammatory and antimicrobial agents . Boll. Chim. Farm. , 143 : 227 – 238 .
   PubMedGoogle Scholar
• Gatto , B. , Capranico , G. and Palumbo , M. 1999 . Drugs acting on DNA topoisomerases: Recent advances and future perspectives . Curr. Pharm. Des. , 5 : 195 – 215 .
   PubMed Web of Science ®Google Scholar
• Cao , Y. and He , W. X. 1998 . Studies of interaction between Safranine T and double helix DNA by Spectral methods . Spectrochim. Acta. , 54 : 883 – 892 .
   Web of Science ®Google Scholar
• Singh , M. P. , Joseph , T. , Kumar , S. and Lown , J. W. 1992 . Chem. Res. Toxicol. , : 5597
   Google Scholar
• Baez , A. , Gonzalez , F. A. , Vazquez , D. and Waring , M. 1983 . Interaction between a 3-nitrobenzothioazole[3, 2-a] quinolinium antitumor drug . Biochem. Pharm. , 32 : 2089 – 2094 .
   PubMed Web of Science ®Google Scholar
• Tilak Raj , T. and Ambekar , S. Y. 1988 . Synthesis of 4-amino pyrimido [4′,5′:4,5] thieno (2,3-b) quinoline- 4(3H)-ones . J. Chem. Res. , 50 : 537 – 551 .
   Google Scholar
• Li , C. J. 2005 . Organic reactions in aqueous media with a focus on carbon-carbon bond formations . Chem. Rev. , 105 : 3095 – 3166 .
   PubMed Web of Science ®Google Scholar
• Kiran , B. M. , Nandeshwarappa , B. P. , Vaidya , V. P. and Mahadevan , K. M. 2007 . Chemistry of substituted quinolines: Thieno[2,3-b] and thiopyrano[2,3-b]quinolines . Phosphorus Sulfur Silicon , 182 : 969 – 980 .
   Web of Science ®Google Scholar
• Nandeshwarappa , B. P. , Aruna Kumar , D. B. , Bhojya Naik , H. S. and Mahadevan , K. M. 2006 . A fast and large-scale synthesis of 3-formyl-2-mercaptoquinolines . Phosphorus, Sulfur Silicon. Relat. Elem. , 181 : 1545 – 1556 .
   Web of Science ®Google Scholar
• Nandeshwarappa , B. P. , Arun Kumar , D. B. , Bhojya Naik , H. S. and Mahadevan , K. M. 2005 . An efficient microwave-assisted synthesis of thieno[2,3-b]quinolines under solvent-free conditions . J. Sulfur. Chem. , 26 : 373 – 379 .
   Web of Science ®Google Scholar
• Lamani , D. S. , Venugopala Reddy , K. R. , Bhojya Naik , H. S. , Savyasachi , A. and Naik , H. R. 2008 . Synthesis and DNA binding studies of novel heterocyclic substituted quinoline Schiff bases: a potent antimicrobial agent . Nucleosides, Nucleotides Nucleic Acids , 27 : 1197 – 1210 .
   PubMed Web of Science ®Google Scholar
• Carlos , A. I. , Rocio , F. G. , Mari , L. , Quiroga , A. , Carbonell , F. C. and Ernest , G. 1997 . Synthesis and antitumor evaluation of new thiazolo[5,4-b]quinoline derivatives . J. Med. Chem. , 40 : 668 – 676 .
   PubMedGoogle Scholar
• Leong , C. O. , MGaskell , E. A. , Martin , R. T. , Heydon , P. B. , Farmer , M. C. , Bibby , P. A. , Cooper , J. A. , Double , T. D. , Bradshaw , M. F. and Stevens , Br. 2003 . Anti-tumor drug candidate 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole induces single-strand breaks and DNA-protein cross-links in sensitive MCF-7 breast cancer cells . J. Cancer. , 88 : 470 – 477 .
   Web of Science ®Google Scholar
• Zuby , G. L. 1988 . Biochemistry , 2nd ed , New York : McMillan .
   Google Scholar
• McCoubery , A. , Latham , H. C. , Cook , P. R. , Rodger , A. and Lowe , G. 1996 . 4-Picoline-2,2′:6′,2″-terpyridine- platinum(II)—A potent intercalator of DNA . FEBS Lett , 380 : 73 – 78 .
   PubMed Web of Science ®Google Scholar
• Li , G. G. , Wang , H. M. and Li , A. Z. 1992 . Molecular Biophysical Chemistry , Beijing : Higher Education Publisher .
   Google Scholar
• Fairley , T. A. , Tidwell , R. R. , Donkor , I. , Naiman , N. A. , Ohemeng , K. A. , Lombardy , R. J. , Bentley , J. A. and Cory , M. J. 1993 . Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles) . J. Med. Chem. , 36 : 1746 – 1753 .
   PubMed Web of Science ®Google Scholar
• Cohen , G. and Eisenberg , H. 1969 . Viscosity and sedimentation study of sonicated DNA-proflavin complexes . Biopolymers , 8 : 45 – 55 .
   Web of Science ®Google Scholar
• Prabhakara , M. C. , Bhojya Naik , H. S. , Krishna , V. and Kumaraswamy , H. M. 2007 . Binding and oxidative cleavage studies of DNA by mixed ligand Co(III) and Ni(II) complexes of quinolo[3,2-b]benzodiazapine and 1,10-phenanthroline . Nucleosides Nucleotides Nucleic Acids , 26 : 459 – 471 .
   PubMed Web of Science ®Google Scholar
• Lamani , D. S. , Venugopala Reddy , K. R. , Bhojya Naik , H. S. , Prakash Naik , H. R. and Sridhar , A. M. 2008 . Synthesis of diquinolineno[1,3,7,9]tetraazacyclododecine-7,15 (14H, 16H)-dibenzene, and DNA binding studies of macrocyclic Co(II), Cu(II) complexes: as new class of antimicrobial agent . J. Macromolecular Sci, Part A. , 45 : 857 – 864 .
   Web of Science ®Google Scholar
• Shahabuddin , S. , Gopal , M. , Sathees , M. and Raghavan , C. 2007 . Intercalating and antitumour activity of 4-oxopyrimido[4’,5’:4,5]thieno(2,3-b)quinoline-4(3H)-one . J. Cancer Mol. , 3 : 139 – 146 .
   Google Scholar
• Prabhakara , M. C. , Basavaraju , B. and Bhojya Naik , H. S. 2007 . Co(III) and Ni(II) complexes containing bioactive ligands: Synthesis, DNA binding, and photocleavage studies . Bioinorg. Chem. Appl. , 320 ( 7 ) : 1 – 7 .
   Google Scholar
• Gopal , M. , Shenoy , S. and Doddamani , L. S. 2003 . 4-Anilinopyrimido[4’5’:4,5]selenolo(2,3- quinoline and 4-piperazino pyrimido[4’5’:4,5]selenolo(2,3-b)quinoline: New DNA intercalating chromophores with antiproliferative activity . J. Photochem. Photobiol. , 72 : 69 – 78 .
   Web of Science ®Google Scholar
• Mee , S. L. , Pierre , A. , Markovits , J. , Atassi , G. , Sablon , A. J. and Saucier , J. M. 1998 . S16020–2, a New highly cytotoxic antitumor olivacine derivative: DNA interaction and DNA topoisomerase II inhibition . J. Molcular Pharmacol , 53 : 213 – 220 .
   PubMed Web of Science ®Google Scholar
• Mossman , T. 1983 . Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays . J. Immun. Meth. , 65 : 55 – 63 .
   PubMed Web of Science ®Google Scholar
• Dua , P. and Gude , R. P. 2006 . Antiproliferative and Antiproteolytic activity of Pentoxifylline in cultures of B16F10 melanoma cells . Cancer Chemother. Pharmacol. , 58 : 195 – 202 .
   PubMed Web of Science ®Google Scholar
• Reichmann , M. E. , Rice , S. A. , Thomas , C. A. and Doty , P. 1954 . A furhter examination of the molecular weight and size of deoxy pentose nucleic acid . J. Am. Chem. Soc. , 76 : 3047 – 3053 .
   Web of Science ®Google Scholar
• Wolfe , A. , Shimer , G. H. and Meehan , T. 1987 . Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA . Biochemistry. , 26 : 6392 – 6396 .
   PubMed Web of Science ®Google Scholar
• Raja , A. , Rajendiran , V. and Maheswari , P. U. 2005 . Copper(II) complexes of tridentate pyridylmethylethylenediamines: role of ligand steric hindrance on DNA binding and cleavage . J. Inorg. Biochem. , 99 : 1717 – 1732 .
   PubMed Web of Science ®Google Scholar
• Zhang , H. , Liu , C. S. , Bu , X. H. and Yang , M. 2005 . Synthesis, crystal structure, cytotoxic activity and DNA-binding properties of the copper (II) and zinc (II) complexes with 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene . J. Inorg. Biochem. , 99 : 1119 – 1125 .
   PubMed Web of Science ®Google Scholar