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

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.

Promoting the Antimicrobial Potency of Synthesized Azo-azomethine Triazole Ligand by Metal Complexing

“…In addition, the overlapping CH signals appeared at 7.16 -8.35 ppm ascribing to the aromatic protons of the two phenyl rings. The noted chemical shift of H 8 , H 9 , H 22 (δ = 7.99, 8.18 ppm) is a characteristic downfield value of protons in o-position for the diazinyl moiety, whereas the downfield shift of the singlet peak of H 24 (8.07) and the up-filed shift of H 20 (7.16) suggested the presence of the hydroxyl group at ortho and meta positions to these two protons respectively [52][53][54]. The proton of the triazole ring appears at 8.35 ppm and a characteristic exchangeable proton of OH appears at 10.32.…”

Functionally Substituted Chemical Organic Compounds: Potential Antimicrobial Substances

“…Dextrose agar was used to determine antifungal properties against Candida albicans and Aspergillus niger. All the compounds showed considerable antimicrobial activity but it was concluded that pyrimidine derivatives having nitro group in their structure showed better antimicrobial properties as compared to other chalcones derivatives [33]. [2,3d] ]pyrimidin-10(4H)one exhibited maximum antimicrobial activity [34].…”

N−SO3H Functionalised Brønsted Acidic Ionic Liquid Catalysed Sequential One‐Pot Synthesis of 2‐Amino‐3‐Cyanopyridines via Claisen‐Schmidt Condensation Under Solvent‐free Condition

“…[34,35] The general route for the synthesis chalcones involve Claisen-Schmidt condensation between acetophenone derivatives and aromatic aldehydes, utilizing strong acidic or basic reagents/catalysts like NaOH, KOH, AlCl 3 and HCl. [36] These methods however have drawbacks associated with catalyst recovery, side-product formation, less product selectivity, longer reaction time, harsh reaction conditions and complicated isolation of products. [37] Eventually, a number of environmentally benign strategies were developed with ionic liquids, [25,[38][39][40] glycerine, [41] microwave [42] and ultrasound-assisted conditions [43] for the efficient synthesis of chalcones.…”

“…Additionally, chalcones represent a class of α, β‐unsaturated aromatic ketones that are present as the core unit in an array of biologically active molecules with antibacterial, anti‐inflammatory, antiviral, anticancer and antifungal activities [34,35] . The general route for the synthesis chalcones involve Claisen‐Schmidt condensation between acetophenone derivatives and aromatic aldehydes, utilizing strong acidic or basic reagents/catalysts like NaOH, KOH, AlCl 3 and HCl [36] . These methods however have drawbacks associated with catalyst recovery, side‐product formation, less product selectivity, longer reaction time, harsh reaction conditions and complicated isolation of products [37] .…”