Synthesis, antitumor, and DNA binding behavior of novel 4-(2-hydroxyquinolin-3-yl)-6-phenyl-5, 6 dihydropyrimidin derivatives in aqueous medium.
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, (1)HNMR, and electronic and mass spectral data. The compounds (2a and 2b) were evaluated 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 (K(b)) observed 4.3 x 10(5) M(-1) for (2a), and 3.8 x 10(5) M(-1) for (2d) suggested that compound (2a) binds more strongly with base pairs than (2d).
Lamani
Devappa S
DS
Department of Studies in Industrial Chemistry, Jnana Sahyadri Kuvempu University, Shankaraghatta, Shimoga District, Karnataka, India.
Reddy
K R Venugopala
KR
Naik
H S Bhojya
HS
Pai
K S R
KS
Kumar
Ravishankar
R
Naik
H R Prakash
HR
Naik
L R
LR
D000042:Absorption; D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D005260:Female; D006801:Humans; D006912:Hydroxyquinolines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009691:Nucleic Acid Denaturation; D011743:Pyrimidines / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013057:Spectrum Analysis; D013778:Tetrazolium Salts; D013844:Thiazoles; D014783:Viscosity; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D000970:Antineoplastic Agents; D047188:Chalcones; D006912:Hydroxyquinolines; D007659:Ketones; D011743:Pyrimidines; D013778:Tetrazolium Salts; D013844:Thiazoles; D014867:Water; D004247:DNA; C022616:thiazolyl blue