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Volume: 9, Issue: 5, May, 2019
DOI: 10.7324/JAPS.2019.90517



Research Article

Synthesis and characterization of novel 1,6-dihydropyrimidine derivatives for their pharmacological properties

Basavaraj Padmashali1, Ballekere Nanjundaswamy Chidananda2, Banuprakash Govindappa3, Siddesh M. Basavaraj4, Sandeep Chandrashekharappa2, Katharigatta N. Venugopala5 & 6

  Author Affiliations


Abstract

The present research work involves the use of commercially available thiophene-2-carbaldehyde as a starting material to construct novel pyrimidine compounds. Synthesis of pyrimidine derivatives has been done by the trimolecular Biginelli condensation reaction, which involves the use of thiophene-2-carbaldehyde with cyano ethylacetate and thiourea to yield 4-oxo-6-(thiophen-2-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (1). The intermediate 1 was methylated using methyl iodide and K2CO3 in dimethylformamide (DMF) which afforded dimethylated derivative 1-methyl-2-(methylthio)-6-oxo-4-(thiophen-2-yl)-1,6-dihydropyrimidine-5-carbonitrile (2). The intermediate compound 2 when refluxed with hydrazine hydrate in ethanol as a solvent led to the formation of the parent compound 2-hydrazineyl-1-methyl-6-oxo-4-(thiophen-2-yl)-1,6-dihydropyrimidine-5-carbonitrile (3), the parent compound 3 was used for the synthesis of carboxamides of N′-(5-cyano-1-methyl-6-oxo-4-(thiophen-2-yl)-1,6-dihydropyrimidin- 2-yl)substituted benzohydrazide (4a–d) and Schiff bases of (E)-2-(2-substituted benzylidenehydrazineyl)-1-methyl- 6-oxo-4-(thiophen-2-yl)-1,6-dihydropyrimidine-5-carbonitrile (5a–g). Selected title compounds are screened for antibacterial, analgesic, and antifungal activities.

Keywords:

Substituted 1, 6-dihydropyrimidine, synthesis, antibacterial, antifungal, analgesic.



Citation: Padmashali B, Chidananda BN, Govindappa B, Basavaraj SM, Chandrashekharappa S, Venugopala KN. Synthesis and characterization of novel 1,6-dihydropyrimidine derivatives for their pharmacological properties. J Appl Pharm Sci, 2019; 9(05):133–140.


Copyright: The Author(s). This is an open access article distributed under the Creative Commons Attribution Non-Commercial License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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