Novel Amalgamation of 2-Styrylchromones and 1,2,4-Triazole: Synthesis, Antimicrobial Evaluation and Docking Study

Synthesis, antimicrobial evaluation, and molecular docking studies of novel chromone based 1,2,3-triazoles

“…Therefore, in continuation of our earlier work on the synthesis of chromone derivatives [33], and owing to the significant features of nitrogen containing heterocycles to modulate the physiochemical properties, herein, we designed and synthesized 1,2,3-triazole tethered chromone derivatives in a single molecular framework to investigate the influence on biological activity and evaluated for their antimicrobial activity with molecular docking study.…”

An Overview of 2‐Styrylchromones: Natural Occurrence, Synthesis, Reactivity and Biological Properties

“…[72] Figure 5). [73] Compounds 139 and 141 presented excellent activity against C. albicans (MIC 25 μg mL -1 ) in comparison with the standard fluconazole (MIC 50 μg mL -1 ). Docking studies indicated good binding interaction at the active site of fungal enzyme P-450 cytochrome lanosterol 14 α-demethylase, whereas good pharmacokinetics and drug-like properties were obtained from ADMET predictions.…”

“…The classical approach involves a three-step sequence: (i) condensation of appropriate 2′-hydroxyacetophenones with cinnamoyl chlorides, (ii) base-promoted Baker-Venkataraman rearrangement [62,63] of the formed esters 31 into the 5-aryl-3-hydroxy-1-(2-hydroxyaryl)penta-2,4-dien-1-ones 32 (in equilibrium with the corresponding diketone form), and (iii) cyclodehydration to afford the desired 2-SCs 33 (Scheme 8). The cinnamoyl chlorides used in the esterification step may be commercially available or can be prepared in situ by treatment of the corresponding cinnamic acids with phosphoryl chloride in dry pyridine at room temperature or 60-90°C [7,8,18,19,32,45,47,[64][65][66][67][68][69][70][71][72][73][74] or with N,N-dicyclohexylcarbodiimide (DCC) in the presence of a catalytic amount of 4-pyrrolidinepyridine (4-PPy) in dichloromethane at room temperature. [13,75] Transposition of the cinnamoyl group from the 2′-position to position 2 of the acetophenone occurs in the presence of potassium hydroxide with DMSO [13,18,19,7,8,32,[67][68][69]71,73] or pyridine [47,64,70,73,74] as solvent, of sodium hydride in THF at reflux [8,45,65] or under less conventional c...…”

“…[75] The last step was originally achieved in a strongly acidic medium (sulfuric acid in acetic acid at reflux), but this is rarely used nowadays. [64,70,74] It has been replaced by use of milder reagent systems, including the use of a few drops of diluted hydrochloric acid in acetic acid, [73] of p-toluenesulfonic acid (PTSA) in DMSO [13,18,19,7,8,65,67,68,72] or of a catalytic amount of iodine in DMSO. [13,18,8,45,68] Individual attempts with use of concentrated sulfuric acid in ethanol at reflux, [66] grinding with phosphorus pentoxide under solventfree conditions [76] and with potassium carbonate in water under classical heating at reflux or under microwave-assisted conditions [77] have also been reported (Scheme 8).…”

“…The results indicate that shorter reaction times and better yields are obtained with the ultrasound-assisted method. [73] The synthesis of 3-substituted 2-SCs by this three-step strategy involves the previously mentioned penta-2,4-dien-1-ones. Various 3-bromo-2-styrylchromones 34 were obtained when 5-aryl-3-hydroxy-1-(2-hydroxyaryl)penta-2,4-dien-1-ones 32 were treated with bromine in 1,4-dioxane [64] and with phenyltrimethylammonium tribromide (PTT) in THF at room temperature (Scheme 9).…”