chromanone oxime ether

The spread of cancer, coupled with the challenges posed by complex treatments, stands as one of the foremost medical issues in today's world. Researchers consistently strive to identify novel compounds with enhanced efficacy and reduced side effects. Aromatase, a pivotal enzyme in estrogen receptor-positive breast cancer, plays a significant role. Estrogens, crucial for human physiology, particularly in women, contribute to sexual development and reproduction. The adverse effects associated with specific aromatase inhibitors underscore the imperative to discover new inhibitors characterized by higher selectivity, lower toxicity, and improved potency.

This research is a basic study in which the semi-prepared aromatase kit was used to investigate synthetic compounds, specifically triazolyl chromanone oxime ethers. The most promising compounds were selected and subjected to molecular docking studies based on the inhibition results obtained.

Out of the 40 compounds examined, seven samples exhibiting the most pronounced inhibitory effects were chosen for further scrutiny and IC50 determination. Notably, derivatives 6b and 20b demonstrated the most robust inhibitory effects, with IC50 values of 0.37 and 0.69 μM, respectively. Examining the interactions between these compounds and the aromatase enzyme revealed a significant relationship with the enzyme's active site.

In conclusion, the evaluation of various derivatives containing the triazolyl chromanone oxime ether structure suggests their considerable potential as aromatase enzyme inhibitors. Further exploration involving the design of structures within this category holds the promise of yielding more effective derivatives for inhibiting this enzyme.

Background and Despite growing list of antifungal agents, their clinical value has been limited by their relatively high risk of toxicity, the emergence of drug resistance, and insufficiencies in their antifungal activity. This situation has led to an ongoing search for potent broad spectrum antifungal agents with low side effects, which can be administered both orally and parenterally. This paper describes synthesis and structural characterization of 2-methyl-3- triazolyl chromanone oxime ethers as potential antifungal agent. Bromination of 2-hydroxyacetophenones with copper (II) bromide followed by reaction with 1,2,4-triazole gave the corresponding α-triazolyl-2-hydroxyacetophenones, which separated as regioisomers. Ring closure of α-triazolyl-2-hydroxyacetophenones with acetaldehyde in acetic acid gave the corresponding 2-methyl-3-triazolyl chromanones predominantly in the trans configuration. The target compounds (oxime ether derivatives) were prepared by reacting corresponding 2-methyl-3-triazolyl chromanone derivatives with O-benzyl hydroxylamine hydrochlorides in methanol at room temperature. All of the target compounds were characterized by their 1H NMR, IR and mass spectral data. A convenient and efficient synthesis and structural characterization of 2-methyl-3-triazolyl chromanone oxime ether as potential antifungal agents has been achieved. 1H-NMR spectra were generally used to assign the stereochemistry of the isomers (E or Z form) of oxime ethers.