M. K. Regal, S. Shabana, S. El‐Metwally
Feb 1, 2020
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Influential Citations
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Journal
Russian Journal of Organic Chemistry
Abstract
Abstract Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate ( 1 ) exhibits a moderate cytotoxic activity against the MCF-7 mammary gland cancer cell line and HePG2 hepatocellular carcinoma cell line and a weak activity against the HCT-116 human colorectal carcinoma cell line. In order to enhance the cytotoxic activity of this compound, it was modified by changing the side-chain substituent and/or forming a new heterocyclic ring fused to the pyridine ring. Heating compound 1 with chloroacetyl chloride gave a mixture of two isomeric O -acylation products ethyl 4-(2-chloroacetoxy)-7-(trifluoromethyl)-quinoline-3-carboxylate and 3-chloro-8-(trifluoromethyl)-2 H -pyrano[3,2- c ]quinoline-2,4(3 H )-dione, whereas the reaction with acetyl chloride in NaOH formed an N -acylation product 1-acetyl-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid. The reactions of compound 1 with urea, thiourea, hydrazine hydrate, hydroxylamine, o -phenylenediamine, phenyl isothiocyanate, and ethyl acetoacetate yielded the corresponding condensation products 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]urea, 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]thiourea, 7-(trifluoromethyl)-1,2-dihydropyrazolo[4,3- c ]quinolin-3-one, 7-(trifluoromethyl)isoxazolo[4,5- c ]quinolin-3(2 H )-one, 3-(trifluoromethyl)-13 H -benzo[2,3][1,4]diazepino[6,5- c ]quinolin-7-ol, 3-phenyl-2-thioxo-8-(trifluoromethyl)-2,3-dihydro-4 H -[1,3]oxazino[5,6- c ]quinolin-4-one and ethyl 8-(trifluoromethyl)-2-methyl-4-oxo-4 H -pyrano[3,2- c ]quinolone 3-carboxylate, respectively. The structures of the synthesized compounds were confirmed by elemental analysis and spectral data.