Abstract
2-Amino-4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile (3) was synthesized by treating cyclohexanone (1) with 2-benzylidenemalononitrile (2) in the presence of ammonium acetate. The reactivity of compound 3 towards dimethylformamide dimethyl acetal (DMF-DMA), carbon disulfide, urea, thiourea, formamide, formic acid, acetyl chloride and isothiocyanate were studied. In addition, the antimicrobial activity of some selected derivatives is reported.
Highlights
Pyrimidoquinolines are important compounds because of their biological properties, which are known to depend mainly on the nature and position of substituents, and include antimalarial [1], anticancer [2], antimicrobial [3, 4], and anti-inflammatory activities [5, 6]
Our aim in the work presented was to synthesize pyrimido[4,5-b]quinolines using tetrahydroqinolinecarbonitriles as building blocks. Such a synthesis of condensed azines is of biological interest due to the formal isoelectronic relationship that exists between the pyrimidine ring and tetrahydroquinoline [12,13,14,15,16,17,18,19,20,21,22,23]
The antifungal activity assays showed that compounds 12, 20a, 22 and 24 display moderate activity against C. albicans, while compound 9a shows strong activity against A. niger and compound 13 shows strong activity against S. cerevisiae
Summary
Pyrimidoquinolines are important compounds because of their biological properties, which are known to depend mainly on the nature and position of substituents, and include antimalarial [1], anticancer [2], antimicrobial [3, 4], and anti-inflammatory activities [5, 6]. Our aim in the work presented was to synthesize pyrimido[4,5-b]quinolines using tetrahydroqinolinecarbonitriles as building blocks Such a synthesis of condensed azines is of biological interest due to the formal isoelectronic relationship that exists between the pyrimidine ring and tetrahydroquinoline [12,13,14,15,16,17,18,19,20,21,22,23]
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