A study of the reaction of phenyl magnesium bromide with various N-(cyanomethyl)oxazolidines showed that product formation (essentially 3-imidazolines and 2-aminomorpholines) is highly sensitive to the substitution pattern and stereochemistry, and appears to involve initial complexation of the Grignard reagent to ring-oxygen.

Aim and Objective:: Nowadays, developing effective antibiotics for bacteria control has become difficult due to increased resistance to the available medicines in the market. Essential oils have very interesting biological properties; some of their components have very powerful antiviral and antibacterial properties. Carthamus caeruleus is a plant that has antibacterial and antioxidant activity due to the presence of an acetylenic compound, Carlina oxide. The aim of this work was to provide for the first time the chemical modifications to the structure of Carlina oxide and the in-silico study of these analogues. Materials and Methods:: The essential oil of Carthamus caeruleus was extracted by steam distillation in a Clevenger-type apparatus. Carlina oxide component was separated by column chromatography. Five new analogues were synthetized and identified by spectroscopic analyses (RMN, IR and SM). Molecular docking simulation study was performed using Molecular Operating Environment software (MOE) on three enzymes of bacterial origin (Streptococcus pyogenesis and Enterococcus faecalis). Results:: Five new compounds derived from Carlina oxide were synthesized (IM8-IM12), and their structures were characterized by infrared (IR), 1H and 13C nuclear magnetic resonance (NMR). The new synthesized compounds were evaluated as mSpeB, DHFR from Enterococcus faecalis and DNA gyrase inhibitors by a docking analysis using MOE. These results show interesting ligand interactions with the three enzymes, and the best result was attributed to the complexes formed with IM9, which had the lowest score. Conclusion:: In fact, these new compounds could lead to powerful approaches for the research and development of new antibiotics.

The reaction of the model combined aminonitrile-oxazolidine system I with a variety of Cn'ignard and other organometallic reagents leads to the heterocyclic structures 3-imidazolines 2 and 2aminomorpholines 3 by tandem addition/substitution reactions. The regioselectivity of the initial attack, and hence the relative proportions of products, varies with the nature of the reagent and the presence of Lewis acidity in the mixture.