Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 591-605 |
| Number of pages | 15 |
| Journal | Nucleosides, Nucleotides and Nucleic Acids |
| Volume | 29 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2010 |
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In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 29, No. 8, 2010, p. 591-605.
Research output: Contribution to journal › Article › peer-review
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. 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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
SN - 1525-7770
VL - 29
SP - 591
EP - 605
JO - Nucleosides, Nucleotides and Nucleic Acids
JF - Nucleosides, Nucleotides and Nucleic Acids
IS - 8
ER -