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Synthesis, Characterization, and Biological Activity of 4-(2-Hydroxy-5-(aryl-diazenyl)phenyl)-6-(aryl)pyrimidin-2-ols Derivatives

DOI: 10.1155/2013/582079

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Abstract:

With the aim of synthesizing new heterocyclic compounds and exploring biological potency, new series of chalcones, that is, 3-(2-hydroxy-5-(aryl-diazenyl)phenyl)-1-(aryl)prop-2-en-1-one and their pyrimidine derivatives, that is, 4-(2-hydroxy-5-(aryl-diazenyl)phenyl)-6-(aryl)pyrimidin-2-ols were synthesized using different aromatic amines and salicylaldehyde as starting moieties. The structures of newly synthesized compounds were confirmed using different spectroscopic techniques such as IR, 1H-NMR, 13C-NMR, and mass spectral analysis, and elemental analysis. The newly synthesized pyrimidines derivatives were screened for their in vitro antibacterial and antifungal activities. It was observed that some of the newly synthesized compounds had shown promising activity against several bacterial and fungal stains. Anti-bacterial activity and anti-fungal activity studies revealed that pyrimidine derivatives consisting of nitro group in their molecular structure possess better activity than their corresponding chalcones. 1. Introduction Chalcones (1,3-diaryl-2-propen-1-ones), one of the major classes of natural products belonging to the flavonoid family, have been recently the subjects of great interest for their interesting pharmacological activities [1, 2]. In fact, the pharmacological properties of chalcones are due to the presence of both α,β-unsaturation and an aromatic ring [3]. Many biological activities have been attributed to this group, such as cytotoxic [4, 5], antimalarial [6, 7], antileishmanial [8, 9], anti-inflammatory [10, 11], anti-HIV [12], antifungal [13], antioxidant [14], and as tyrosine kinase inhibitors [15]. Due to their abundance in plants and ease of synthesis, this class of compounds has generated great interest for possible therapeutic uses [16, 17]. Of the many methods available for the synthesis of chalcones, the most widely used method is the base catalyzed Claisen-Schmidt reaction [18] in which the condensation of a ketone with an aldehyde is carried out in the presence of aqueous NaOH [19], Ba(OH)2 [20], KOH, and so forth. The acid catalyzed methodologies include the use of silica sulfuric acid [21], AlCl3, dry HCl, and so forth [22]. Chalcone derivatives are very versatile as physiologically active compounds and substrates for the evaluation of various organic syntheses. Chalcones are valuable intermediates in the synthesis of many active pharmaceutical drugs like biosynthesis of flavonoids and Auwers synthesis of flavones [23]. Pyrimidine and its derivatives are most important nitrogen based heterocycles which play a vital

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