Synthesis, antitumor, and DNA binding behavior of novel 4-(2-Hydroxyquinolin-3-yl)-6-Phenyl-5, 6 dihydropyrimidin derivatives in aqueous medium

D.S. Lamani, K.R.V. Reddy, H.S.B. Naik, K.S.R. Pai, R. Kumar, H.R.P. Naik, L.R. Naik

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

This article deals with the synthesis of 4-(2-hydroxyquinolin-3-yl)-6- phenyl-5,6-dihydropyrimidin derivatives (2a-f), on condensation with various aromatic aldehydes and ketones in aqueous ethanolic NaOH solution yielding the corresponding chalcones (3). These chalcones were further reacted with thiourea/urea in the presence of a base, which led to the formation of the titled derivatives (2a-f). The newly synthesized heterocyles were characterized by elemental analysis, FTIR, 1HNMR, and electronic and mass spectral data. The compounds (2a and 2b) were evulated for in vitro cyctotoxicity against human breast adenocarcinoma cell (MCF-7). In MTT cytotoxicity studies, both quinolinde derivatives were found most effective. The binding interaction behavior of the compound (2a) and (2d) with calf thymus-DNA (CT-DNA) was studied by electronic spectra, viscosity measurements, and thermal denaturation studies. On binding to CT-DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) observed 4.3 × 105 M-1 for (2a), and 3.8 × 105 M-1 for (2d) suggested that compound (2a) binds more strongly with base pairs than (2d). © 2010 Taylor and Francis Group, LLC.
Original languageEnglish
Pages (from-to)591-605
Number of pages15
JournalNucleosides, Nucleotides and Nucleic Acids
Volume29
Issue number8
DOIs
Publication statusPublished - 2010

Fingerprint

Chalcones
Derivatives
Thiourea
DNA
MCF-7 Cells
Fourier Transform Infrared Spectroscopy
Ketones
Aldehydes
Viscosity
Base Pairing
Urea
Adenocarcinoma
Denaturation
Breast
Hot Temperature
Viscosity measurement
Cytotoxicity
Absorption spectra
Condensation
Chemical analysis

Cite this

@article{33851728bab44335bb7ae2eb34146055,
title = "Synthesis, antitumor, and DNA binding behavior of novel 4-(2-Hydroxyquinolin-3-yl)-6-Phenyl-5, 6 dihydropyrimidin derivatives in aqueous medium",
abstract = "This article deals with the synthesis of 4-(2-hydroxyquinolin-3-yl)-6- phenyl-5,6-dihydropyrimidin derivatives (2a-f), on condensation with various aromatic aldehydes and ketones in aqueous ethanolic NaOH solution yielding the corresponding chalcones (3). These chalcones were further reacted with thiourea/urea in the presence of a base, which led to the formation of the titled derivatives (2a-f). The newly synthesized heterocyles were characterized by elemental analysis, FTIR, 1HNMR, and electronic and mass spectral data. The compounds (2a and 2b) were evulated for in vitro cyctotoxicity against human breast adenocarcinoma cell (MCF-7). In MTT cytotoxicity studies, both quinolinde derivatives were found most effective. The binding interaction behavior of the compound (2a) and (2d) with calf thymus-DNA (CT-DNA) was studied by electronic spectra, viscosity measurements, and thermal denaturation studies. On binding to CT-DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) observed 4.3 × 105 M-1 for (2a), and 3.8 × 105 M-1 for (2d) suggested that compound (2a) binds more strongly with base pairs than (2d). {\circledC} 2010 Taylor and Francis Group, LLC.",
author = "D.S. Lamani and K.R.V. Reddy and H.S.B. Naik and K.S.R. Pai and R. Kumar and H.R.P. Naik and L.R. Naik",
note = "Cited By :2 Export Date: 10 November 2017 CODEN: NNNAF Correspondence Address: Reddy, K. R. V.; Department of Studies in Industrial Chemistry, Jnana Sahyadri Kuvempu University, Shankaraghatta-577 451, Shimoga District, Karnataka, India; email: venurashmi30@rediffmail.com Chemicals/CAS: DNA, 9007-49-2; Aldehydes; Antineoplastic Agents; Chalcones; DNA, 9007-49-2; Hydroxyquinolines; Ketones; Pyrimidines; Tetrazolium Salts; Thiazoles; Water, 7732-18-5; thiazolyl blue, 298-93-1 References: Hasegawa, S., Masunaga, K., Muto, M., Hanada, S., (1991) Chem. Abstr., pp. 34897k. , JP 0232, 086 [90 32, 086], 1990, 114; Peacocke, A.R., (1973) In Heterocyclic Compounds: The Acridines, , Acheson, R. M., Ed.; Wiley Interscience: New York; Ledochowski, A., Ledakin-Anticancerous Medicine 1-Nitro-9- (3-dimethylaminopropylamino) acridine dihydrochloride monohydrate (1976) Mater. Med. Polon., 8, pp. 237-251; Afonso, A., Weinstein, J., Gentles, M., (1995) J. US, 5, p. 382. , Chem. Abstr. 5721995, 122, 213949r; (1991) Ukrainskii Khimicheskii Zhurrnal (Russion Edition), 57 (12), pp. 1325-1328; Ukrainets, V., Taran, S.G., Sidorenko, L.V., Gorokhova, O.V., Ogirenko, A.A., Turov, N.I., 4-Hydroxy- 2-quinolones. 37. Simple synthesis of 1-R-2-oxo-3,4- dihydroxyquinolines (1996) Khim.Geterotsikl. Soedin Filimonova., 8, pp. 1113-1118; Petal, N.C., Mehta, A.G., Synthesis of bisazo acid dyes based on 4-hydroxy-1-phenylquinoline-2(1H)- one system and their dyeing performance on various fabrics (2001) Asian J. Chem., 13, pp. 1385-1388; Munawar, M.A., Azad, M., Siddiqu, H.L., Nasim, F.H., Synthesis and antimicrobial studies of some quinolinylpyrimidine derivatives (2008) J. Chin. Chem. Soc, 55, pp. 394-400; Joshi, A.A., Viswanathan, C.L., Recent developments in antimalarial drug discovery. (2006) Anti-Infect Agent Med Chem, 5, pp. 105-122; El-Sayed, O.A., El-Baih, F.M.E., El-Aqeel, Sh.I., Al Bassam, B.A., Hussein, M.E., Novel 4- aminopyrimido[4,5-b]quinoline derivatives as potential antimicrobial agents (2002) Boll. Chem. Farmac, 141 (6), pp. 461-465; El-Sayed, O.A., Al-Bassam, B.A., Hussein, M.E., Synthesis of some novel quinoline-3-carboxylic acids and pyrimidoquinoline derivatives as potential antimicrobial agents (2002) Arch. Pharm., 335, pp. 403-410; Glushkov, V.A., Stryapunina, O.G., Gorbunov, A.A., Maiorova, O.A., Slepukhin, P.A., Ryabukhina, S.Ya., Khorosheva, E.V., Shklyaev, Y.V., 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 (2010) Tetrahedron, 66, pp. 721-729; El-Sayed, O.A., Al-Turki, T.M., Al-Daffiri, H.M., Al-Bassam, B.A., Hussein, M.E., Pyrimidoquinoline derivatives as anti-inflammatory and antimicrobial agents (2004) Boll. Chim. Farm., 143, pp. 227-238; Gatto, B., Capranico, G., Palumbo, M., Drugs acting on DNA topoisomerases: Recent advances and future perspectives (1999) Curr. Pharm. Des., 5, pp. 195-215; Cao, Y., He, W.X., Studies of interaction between Safranine T and double helix DNA by Spectral methods (1998) Spectrochim. Acta., 54, pp. 883-892; Singh, M.P., Joseph, T., Kumar, S., Lown, J.W., (1992) Chem. Res. Toxicol., p. 5597; Baez, A., Gonzalez, F.A., Vazquez, D., Waring, M., Interaction between a 3-nitrobenzothioazole[3, 2-a] quinolinium antitumor drug (1983) Biochem. Pharm., 32, pp. 2089-2094; Tilak Raj, T., Ambekar, S.Y., Synthesis of 4-amino pyrimido [4,5:4, 5] thieno (2,3-b) quinoline- 4(3H)-ones (1988) J. Chem. Res., 50, pp. 537-551; Li, C.J., Organic reactions in aqueous media with a focus on carbon-carbon bond formations (2005) Chem. Rev., 105, pp. 3095-3166; Kiran, B.M., Nandeshwarappa, B.P., Vaidya, V.P., Mahadevan, K.M., Chemistry of substituted quinolines: Thieno[2,3-b] and thiopyrano[2,3-b]quinolines (2007) Phosphorus Sulfur Silicon, 182, pp. 969-980; Nandeshwarappa, B.P., Aruna Kumar, D.B., Bhojya Naik, H.S., Mahadevan, K.M., A fast and largescale synthesis of 3-formyl-2-mercaptoquinolines (2006) Phosphorus, Sulfur Silicon. Relat. Elem., 181, pp. 1545-1556; Nandeshwarappa, B.P., Arun Kumar, D.B., Bhojya Naik, H.S., Mahadevan, K.M., An efficient microwave-assisted synthesis of thieno[2,3-b]quinolines under solvent-free conditions (2005) J. Sulfur. Chem., 26, pp. 373-379; Lamani, D.S., Venugopala Reddy, K.R., Bhojya Naik, H.S., Savyasachi, A., Naik, H.R., Synthesis and DNA binding studies of novel heterocyclic substituted quinoline Schiff bases: A potent antimicrobial agent. (2008) Nucleosides, Nucleotides Nucleic Acids, 27, pp. 1197-1210; Carlos, A.I., Rocio, F.G., Mari, L., Quiroga, A., Carbonell, F.C., Ernest, G., Synthesis and antitumor evaluation of new thiazolo[5,4-b]quinoline derivatives (1997) J. Med. Chem., 40, pp. 668-676; Leong, C.O., Mgaskell, E.A., Martin, R.T., Heydon, P.B., Farmer, M.C., Bibby, P.A., Cooper, J.A., Stevens, Br., 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. (2003) J. Cancer., 88, pp. 470-477; Zuby, G.L., (1988) Biochemistry, , 2nd ed. McMillan, New York; McCoubery, A., Latham, H.C., Cook, P.R., Rodger, A., Lowe, G., 4-Picoline-2, 2:6,2-terpyridineplatinum(II)-A potent intercalator of DNA (1996) FEBS Lett., 380, pp. 73-78; (1992) Molecular Biophysical Chemistry, , Li, G.G.; Wang, H.M.; Li, A.Z.; Eds., Beijing: Higher Education Publisher; Fairley, T.A., Tidwell, R.R., Donkor, I., Naiman, N.A., Ohemeng, K.A., Lombardy, R.J., Bentley, J.A., Cory, M.J., Structure DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles). (1993) J. Med. Chem., 36, pp. 1746-1753; Cohen, G., Eisenberg, H., Viscosity and sedimentation study of sonicated DNA-proflavin complexes. (1969) Biopolymers, 8, pp. 45-55; Prabhakara, M.C., Bhojya Naik, H.S., Krishna, V., Kumaraswamy, H.M., 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 (2007) Nucleosides Nucleotides Nucleic Acids, 26, pp. 459-471; Lamani, D.S., Venugopala Reddy, K.R., Bhojya Naik, H.S., Prakash Naik, H.R., Sridhar, A.M., 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 (2008) J. Macromolecular Sci, Part A., 45, pp. 857-864; Shahabuddin, S., Gopal, M., Sathees, M., Raghavan, C., Intercalating and antitumour activity of 4-oxopyrimido[4',5':4,5] thieno(2,3-b)quinoline-4(3H)-one (2007) J. Cancer Mol., 3, pp. 139-146; Prabhakara, M.C., Basavaraju, B., Bhojya Naik, H.S., Co(III) and Ni(II) complexes containing bioactive ligands: Synthesis DNA binding, and photocleavage studies (2007) Bioinorg. Chem. Appl., 320 (7), pp. 1-7; Gopal, M., Shenoy, S., Doddamani, L.S., 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 (2003) J. Photochem. Photobiol., 72, pp. 69-78; Mee, S.L., Pierre, A., Markovits, J., Atassi, G., Sablon, A.J., Saucier, J.M., S16020-2, a New highly cytotoxic antitumor olivacine derivative: DNA interaction and DNA topoisomerase II inhibition. (1998) J. Molcular Pharmacol, 53, pp. 213-220; Mossman, T., Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays (1983) J. Immun. Meth., 65, pp. 55-63; Dua, P., Gude, R.P., Antiproliferative and Antiproteolytic activity of Pentoxifylline in cultures of B16F10 melanoma cells (2006) Cancer Chemother. Pharmacol., 58, pp. 195-202; Reichmann, M.E., Rice, S.A., Thomas, C.A., Doty, P., A furhter examination of the molecular weight and size of deoxy pentose nucleic acid (1954) J. Am. Chem. Soc., 76, pp. 3047-3053; Wolfe, A., Shimer, G.H., Meehan, T., Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. (1987) Biochemistry., 26, pp. 6392-6396; Raja, A., Rajendiran, V., Maheswari, P.U., Copper(II) complexes of tridentate pyridylmethylethylenediamines: Role of ligand steric hindrance on DNA binding and cleavage (2005) J. Inorg. Biochem., 99, pp. 1717-1732; Zhang, H., Liu, C.S., Bu, X.H., Yang, M., Synthesis crystal structure, cytotoxic activity and DNAbinding properties of the copper (II) and zinc (II) complexes with 1-[3-(2-pyridyl)pyrazol-1- ylmethyl]naphthalene (2005) J. Inorg. Biochem., 99, pp. 1119-1125",
year = "2010",
doi = "10.1080/15257770.2010.496275",
language = "English",
volume = "29",
pages = "591--605",
journal = "Nucleosides and Nucleotides",
issn = "0732-8311",
publisher = "Taylor and Francis Ltd.",
number = "8",

}

Synthesis, antitumor, and DNA binding behavior of novel 4-(2-Hydroxyquinolin-3-yl)-6-Phenyl-5, 6 dihydropyrimidin derivatives in aqueous medium. / Lamani, D.S.; Reddy, K.R.V.; Naik, H.S.B.; Pai, K.S.R.; Kumar, R.; Naik, H.R.P.; Naik, L.R.

In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 29, No. 8, 2010, p. 591-605.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis, antitumor, and DNA binding behavior of novel 4-(2-Hydroxyquinolin-3-yl)-6-Phenyl-5, 6 dihydropyrimidin derivatives in aqueous medium

AU - Lamani, D.S.

AU - Reddy, K.R.V.

AU - Naik, H.S.B.

AU - Pai, K.S.R.

AU - Kumar, R.

AU - Naik, H.R.P.

AU - Naik, L.R.

N1 - Cited By :2 Export Date: 10 November 2017 CODEN: NNNAF Correspondence Address: Reddy, K. R. V.; Department of Studies in Industrial Chemistry, Jnana Sahyadri Kuvempu University, Shankaraghatta-577 451, Shimoga District, Karnataka, India; email: venurashmi30@rediffmail.com Chemicals/CAS: DNA, 9007-49-2; Aldehydes; Antineoplastic Agents; Chalcones; DNA, 9007-49-2; Hydroxyquinolines; Ketones; Pyrimidines; Tetrazolium Salts; Thiazoles; Water, 7732-18-5; thiazolyl blue, 298-93-1 References: Hasegawa, S., Masunaga, K., Muto, M., Hanada, S., (1991) Chem. Abstr., pp. 34897k. , JP 0232, 086 [90 32, 086], 1990, 114; Peacocke, A.R., (1973) In Heterocyclic Compounds: The Acridines, , Acheson, R. M., Ed.; Wiley Interscience: New York; Ledochowski, A., Ledakin-Anticancerous Medicine 1-Nitro-9- (3-dimethylaminopropylamino) acridine dihydrochloride monohydrate (1976) Mater. Med. Polon., 8, pp. 237-251; Afonso, A., Weinstein, J., Gentles, M., (1995) J. US, 5, p. 382. , Chem. Abstr. 5721995, 122, 213949r; (1991) Ukrainskii Khimicheskii Zhurrnal (Russion Edition), 57 (12), pp. 1325-1328; Ukrainets, V., Taran, S.G., Sidorenko, L.V., Gorokhova, O.V., Ogirenko, A.A., Turov, N.I., 4-Hydroxy- 2-quinolones. 37. Simple synthesis of 1-R-2-oxo-3,4- dihydroxyquinolines (1996) Khim.Geterotsikl. Soedin Filimonova., 8, pp. 1113-1118; Petal, N.C., Mehta, A.G., Synthesis of bisazo acid dyes based on 4-hydroxy-1-phenylquinoline-2(1H)- one system and their dyeing performance on various fabrics (2001) Asian J. Chem., 13, pp. 1385-1388; Munawar, M.A., Azad, M., Siddiqu, H.L., Nasim, F.H., Synthesis and antimicrobial studies of some quinolinylpyrimidine derivatives (2008) J. Chin. Chem. Soc, 55, pp. 394-400; Joshi, A.A., Viswanathan, C.L., Recent developments in antimalarial drug discovery. (2006) Anti-Infect Agent Med Chem, 5, pp. 105-122; El-Sayed, O.A., El-Baih, F.M.E., El-Aqeel, Sh.I., Al Bassam, B.A., Hussein, M.E., Novel 4- aminopyrimido[4,5-b]quinoline derivatives as potential antimicrobial agents (2002) Boll. Chem. Farmac, 141 (6), pp. 461-465; El-Sayed, O.A., Al-Bassam, B.A., Hussein, M.E., Synthesis of some novel quinoline-3-carboxylic acids and pyrimidoquinoline derivatives as potential antimicrobial agents (2002) Arch. Pharm., 335, pp. 403-410; Glushkov, V.A., Stryapunina, O.G., Gorbunov, A.A., Maiorova, O.A., Slepukhin, P.A., Ryabukhina, S.Ya., Khorosheva, E.V., Shklyaev, Y.V., 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 (2010) Tetrahedron, 66, pp. 721-729; El-Sayed, O.A., Al-Turki, T.M., Al-Daffiri, H.M., Al-Bassam, B.A., Hussein, M.E., Pyrimidoquinoline derivatives as anti-inflammatory and antimicrobial agents (2004) Boll. Chim. Farm., 143, pp. 227-238; Gatto, B., Capranico, G., Palumbo, M., Drugs acting on DNA topoisomerases: Recent advances and future perspectives (1999) Curr. Pharm. Des., 5, pp. 195-215; Cao, Y., He, W.X., Studies of interaction between Safranine T and double helix DNA by Spectral methods (1998) Spectrochim. Acta., 54, pp. 883-892; Singh, M.P., Joseph, T., Kumar, S., Lown, J.W., (1992) Chem. Res. Toxicol., p. 5597; Baez, A., Gonzalez, F.A., Vazquez, D., Waring, M., Interaction between a 3-nitrobenzothioazole[3, 2-a] quinolinium antitumor drug (1983) Biochem. Pharm., 32, pp. 2089-2094; Tilak Raj, T., Ambekar, S.Y., Synthesis of 4-amino pyrimido [4,5:4, 5] thieno (2,3-b) quinoline- 4(3H)-ones (1988) J. Chem. Res., 50, pp. 537-551; Li, C.J., Organic reactions in aqueous media with a focus on carbon-carbon bond formations (2005) Chem. Rev., 105, pp. 3095-3166; Kiran, B.M., Nandeshwarappa, B.P., Vaidya, V.P., Mahadevan, K.M., Chemistry of substituted quinolines: Thieno[2,3-b] and thiopyrano[2,3-b]quinolines (2007) Phosphorus Sulfur Silicon, 182, pp. 969-980; Nandeshwarappa, B.P., Aruna Kumar, D.B., Bhojya Naik, H.S., Mahadevan, K.M., A fast and largescale synthesis of 3-formyl-2-mercaptoquinolines (2006) Phosphorus, Sulfur Silicon. Relat. Elem., 181, pp. 1545-1556; Nandeshwarappa, B.P., Arun Kumar, D.B., Bhojya Naik, H.S., Mahadevan, K.M., An efficient microwave-assisted synthesis of thieno[2,3-b]quinolines under solvent-free conditions (2005) J. Sulfur. Chem., 26, pp. 373-379; Lamani, D.S., Venugopala Reddy, K.R., Bhojya Naik, H.S., Savyasachi, A., Naik, H.R., Synthesis and DNA binding studies of novel heterocyclic substituted quinoline Schiff bases: A potent antimicrobial agent. (2008) Nucleosides, Nucleotides Nucleic Acids, 27, pp. 1197-1210; Carlos, A.I., Rocio, F.G., Mari, L., Quiroga, A., Carbonell, F.C., Ernest, G., Synthesis and antitumor evaluation of new thiazolo[5,4-b]quinoline derivatives (1997) J. Med. Chem., 40, pp. 668-676; Leong, C.O., Mgaskell, E.A., Martin, R.T., Heydon, P.B., Farmer, M.C., Bibby, P.A., Cooper, J.A., Stevens, Br., 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. (2003) J. Cancer., 88, pp. 470-477; Zuby, G.L., (1988) Biochemistry, , 2nd ed. McMillan, New York; McCoubery, A., Latham, H.C., Cook, P.R., Rodger, A., Lowe, G., 4-Picoline-2, 2:6,2-terpyridineplatinum(II)-A potent intercalator of DNA (1996) FEBS Lett., 380, pp. 73-78; (1992) Molecular Biophysical Chemistry, , Li, G.G.; Wang, H.M.; Li, A.Z.; Eds., Beijing: Higher Education Publisher; Fairley, T.A., Tidwell, R.R., Donkor, I., Naiman, N.A., Ohemeng, K.A., Lombardy, R.J., Bentley, J.A., Cory, M.J., Structure DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles). (1993) J. Med. Chem., 36, pp. 1746-1753; Cohen, G., Eisenberg, H., Viscosity and sedimentation study of sonicated DNA-proflavin complexes. (1969) Biopolymers, 8, pp. 45-55; Prabhakara, M.C., Bhojya Naik, H.S., Krishna, V., Kumaraswamy, H.M., 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 (2007) Nucleosides Nucleotides Nucleic Acids, 26, pp. 459-471; Lamani, D.S., Venugopala Reddy, K.R., Bhojya Naik, H.S., Prakash Naik, H.R., Sridhar, A.M., 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 (2008) J. Macromolecular Sci, Part A., 45, pp. 857-864; Shahabuddin, S., Gopal, M., Sathees, M., Raghavan, C., Intercalating and antitumour activity of 4-oxopyrimido[4',5':4,5] thieno(2,3-b)quinoline-4(3H)-one (2007) J. Cancer Mol., 3, pp. 139-146; Prabhakara, M.C., Basavaraju, B., Bhojya Naik, H.S., Co(III) and Ni(II) complexes containing bioactive ligands: Synthesis DNA binding, and photocleavage studies (2007) Bioinorg. Chem. Appl., 320 (7), pp. 1-7; Gopal, M., Shenoy, S., Doddamani, L.S., 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 (2003) J. Photochem. Photobiol., 72, pp. 69-78; Mee, S.L., Pierre, A., Markovits, J., Atassi, G., Sablon, A.J., Saucier, J.M., S16020-2, a New highly cytotoxic antitumor olivacine derivative: DNA interaction and DNA topoisomerase II inhibition. (1998) J. Molcular Pharmacol, 53, pp. 213-220; Mossman, T., Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays (1983) J. Immun. Meth., 65, pp. 55-63; Dua, P., Gude, R.P., Antiproliferative and Antiproteolytic activity of Pentoxifylline in cultures of B16F10 melanoma cells (2006) Cancer Chemother. Pharmacol., 58, pp. 195-202; Reichmann, M.E., Rice, S.A., Thomas, C.A., Doty, P., A furhter examination of the molecular weight and size of deoxy pentose nucleic acid (1954) J. Am. Chem. Soc., 76, pp. 3047-3053; Wolfe, A., Shimer, G.H., Meehan, T., Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. (1987) Biochemistry., 26, pp. 6392-6396; Raja, A., Rajendiran, V., Maheswari, P.U., Copper(II) complexes of tridentate pyridylmethylethylenediamines: Role of ligand steric hindrance on DNA binding and cleavage (2005) J. Inorg. Biochem., 99, pp. 1717-1732; Zhang, H., Liu, C.S., Bu, X.H., Yang, M., Synthesis crystal structure, cytotoxic activity and DNAbinding properties of the copper (II) and zinc (II) complexes with 1-[3-(2-pyridyl)pyrazol-1- ylmethyl]naphthalene (2005) J. Inorg. Biochem., 99, pp. 1119-1125

PY - 2010

Y1 - 2010

N2 - This article deals with the synthesis of 4-(2-hydroxyquinolin-3-yl)-6- phenyl-5,6-dihydropyrimidin derivatives (2a-f), on condensation with various aromatic aldehydes and ketones in aqueous ethanolic NaOH solution yielding the corresponding chalcones (3). These chalcones were further reacted with thiourea/urea in the presence of a base, which led to the formation of the titled derivatives (2a-f). The newly synthesized heterocyles were characterized by elemental analysis, FTIR, 1HNMR, and electronic and mass spectral data. The compounds (2a and 2b) were evulated for in vitro cyctotoxicity against human breast adenocarcinoma cell (MCF-7). In MTT cytotoxicity studies, both quinolinde derivatives were found most effective. The binding interaction behavior of the compound (2a) and (2d) with calf thymus-DNA (CT-DNA) was studied by electronic spectra, viscosity measurements, and thermal denaturation studies. On binding to CT-DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) observed 4.3 × 105 M-1 for (2a), and 3.8 × 105 M-1 for (2d) suggested that compound (2a) binds more strongly with base pairs than (2d). © 2010 Taylor and Francis Group, LLC.

AB - This article deals with the synthesis of 4-(2-hydroxyquinolin-3-yl)-6- phenyl-5,6-dihydropyrimidin derivatives (2a-f), on condensation with various aromatic aldehydes and ketones in aqueous ethanolic NaOH solution yielding the corresponding chalcones (3). These chalcones were further reacted with thiourea/urea in the presence of a base, which led to the formation of the titled derivatives (2a-f). The newly synthesized heterocyles were characterized by elemental analysis, FTIR, 1HNMR, and electronic and mass spectral data. The compounds (2a and 2b) were evulated for in vitro cyctotoxicity against human breast adenocarcinoma cell (MCF-7). In MTT cytotoxicity studies, both quinolinde derivatives were found most effective. The binding interaction behavior of the compound (2a) and (2d) with calf thymus-DNA (CT-DNA) was studied by electronic spectra, viscosity measurements, and thermal denaturation studies. On binding to CT-DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) observed 4.3 × 105 M-1 for (2a), and 3.8 × 105 M-1 for (2d) suggested that compound (2a) binds more strongly with base pairs than (2d). © 2010 Taylor and Francis Group, LLC.

U2 - 10.1080/15257770.2010.496275

DO - 10.1080/15257770.2010.496275

M3 - Article

VL - 29

SP - 591

EP - 605

JO - Nucleosides and Nucleotides

JF - Nucleosides and Nucleotides

SN - 0732-8311

IS - 8

ER -