A multifaceted approach comprising MCR (multicomponent reaction), amination and stereoselective reduction reactions was used to synthesize new pyrrolidine-based iminosugars. The key step of this strategy involves the contruction of a highly functionalised pyrroldine ring skeleton through MCR approach. Subsequently, amination and reduction reactions to the ring skeleton provide a quick access to new pyrrolidine-based imino sugars. The iminosugars were then tested against alpha glucosidase activity in which one compound (4-((4-methoxyphenyl)amino)pyrrolidin-3-ol), was found to be the most potent at low dosage.
A convenient method for the activation of aryl‐oximes is reported using 1,1,2,2‐tetrafluoro‐N,N‐dimethylethylamine (TFEDMA) as a scalable and efficient reagent. Aryl‐aldoximes led to aryl‐cyanides while aryl‐ketoximes provided aryl‐amides in moderate to excellent yields. The iminium form of TFEDMA acted as a fluorinated version of the well‐known Vilsmeier reagent. Aryl cyanides and aryl amides are valuable synthetic units in natural products and drug candidates. The cyano group is also useful in polymer chemistry for the preparation of photovoltaic cells and LEDs.
Methicillin-resistant Staphylococcus aureus (MRSA) continues to be one of the main causes of hospital-acquired infections in all regions of the world, while linezolid is one of the only commercially available oral antibiotics available against this dangerous gram-positive pathogen. In this study, the antibacterial activity from 32 analogues of synthetic gamma-lactam heterocycles against MRSA was determined. Amongst screened analogues for the minimum inhibitory concentration (MIC) assay, compound MFM514 displayed good inhibitory activity with MIC values of 7.8–15.6 µg/mL against 30 MRSA and 12 methicillin-sensitive S. aureus (MSSA) clinical isolates, while cytotoxicity evaluations displayed a mean inhibitory concentration (IC50) value of > 625 µg/mL, displaying a potential to becoming as a lead compound. In subsequent animal studies for MFM514, a single-dose oral acute toxicity test revealed an estimated mean lethal dose (LD50) value of <5000 mg/kg, while in the mice infection test, a mean effective dose (ED50) value of 29.39 mg/kg was obtained via oral administration. These results suggest that gamma-lactam carbon skeleton, particularly MFM514, is highly recommended to be evaluated further as a new safe and efficacious orally delivered antibacterial agent against MRSA.
The asymmetric unit of the title compound, C9H15NO4, consists of a functionalized pyrrolidine ring having an envelope conformation, synthesized as an ethyl ester. The molecule has three chiral centres and crystallized as a racemic mixture. In the crystal, molecules are linked by pairwise O—H...O bonds, generating dimers with twofold rotational symmetry.
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