Synthesis of α-bromocarbonyl compounds: recent advances

Vekariya, Rajesh H.

doi:10.1016/j.tet.2014.04.027

Cited by 42 publications

(22 citation statements)

References 119 publications

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“…In the first step, 1‐(substituted phenyl)ethanone derivatives were brominated using copper(II) bromide in ethyl acetate resulting in 2‐bromo‐1‐(substituted phenyl)ethanones. For these types of bromination reactions, acetic‐acid medium is generally used; however, in the current study, copper(II) bromide was preferred since in acetic medium, structures containing phenolic parts can direct the bromine to be substituted over the ring system. In the second step, through the Hantzsch thiazole synthesis, 2‐bromo‐1‐(substituted phenyl)ethanones and various pyridinethioamides were reacted in ethanol to obtain either 2/3/4‐[2‐(pyridin‐2/3/4‐yl)thiazol‐4‐yl]phenol or 4‐substituted‐2‐[2‐(pyridin‐2/3/4‐yl)thiazol‐4‐yl]phenol structured compounds with yields ranging from 65 to 82% (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Pyridine‐substituted thiazolylphenol derivatives: Synthesis, modeling studies, aromatase inhibition, and antiproliferative activity evaluation

Ertaş

Şahin

Berk

et al. 2018

Archiv der Pharmazie

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Drugs used in breast cancer treatments target the suppression of estrogen biosynthesis. During this suppression, the main goal is to inhibit the aromatase enzyme that is responsible for the cyclization and structuring of estrogens either with steroid or non-steroidal-type inhibitors. Non-steroidal derivatives generally have a planar aromatic structure attached to the triazole ring system in their structures, which inhibits hydroxylation reactions during aromatization by coordinating the heme group. Bioisosteric replacement of the triazole ring system and development of aromatic/cyclic structures of the side chain can increase the selectivity for aromatase enzyme inhibition. In this study, pyridine-substituted thiazolylphenol derivatives, which are non-steroidal triazole bioisosteres, were synthesized using the Hantzsch method, and physical analysis and structural determination studies were performed. The IC values of the compounds were determined by a fluorescence-based aromatase inhibition assay. Then, their antiproliferative activities on the MCF7 and HEK 293 cell lines were evaluated with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Furthermore, the crystal structure of human placental aromatase was subjected to a series of docking experiments to identify the possible interactions between the most active structure and the active site. Lastly, an in silico technique was performed to analyze and predict the drug-likeness, molecular and ADME properties of the synthesized molecules.

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Section: Resultsmentioning

confidence: 99%

Pyridine‐substituted thiazolylphenol derivatives: Synthesis, modeling studies, aromatase inhibition, and antiproliferative activity evaluation

Ertaş

Şahin

Berk

et al. 2018

Archiv der Pharmazie

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“…The α‐bromination of carbonyl compounds under electrochemical conditions has received much attention due to the fact that the resulting products are useful intermediates in the syntheses of biologically active compounds …”

Section: Electrochemical α‐Halogenation Of Carbonyl Compoundsmentioning

confidence: 99%

Recent Advances in the Electrochemical α‐C–H Bond Functionalization of Carbonyl Compounds

Liang

Zeng

et al. 2018

Adv Synth Catal

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The α‐C–H functionalization of carbonyl compounds represents a cornerstone of organic chemistry. Site‐selective α‐C−H bond functionalization of carbonyl compounds to afford more versatile functionalized groups has become a promising strategy for atom‐economical C−C and C−X bond formation. Organic electrosynthesis is revolutionizing the nature of organic synthesis, and this field has seen explosive growth in recent years. In this review, we discuss advances in the use of electrochemistry for the α‐C–H oxidative functionalization of carbonyl compounds published since 2000.

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“…Other useful bromine carriers are dibromodimethylhydantoin, dioxane dibromide, pyridine hydrobromide dibromide, and various quaternary ammonium polybromides [38].…”

Section: Bromination Using Bromine Carriersmentioning

confidence: 99%