We describe that vinyl-oxadiazoles function as a new and efficient nucleophilic partner for the Morita-Baylis-Hillman (MBH) reaction. The reaction between 5-vinyl-3-aryl-1,2,4-oxadiazoles and aromatic and aliphatic aldehydes, catalyzed by DABCO in the absence of solvent, showed high efficiency to afford a new class of heterocyclic MBH adducts with potential biological activity on yields up to 99% and short reaction times. These synthetically attractive adducts bear a heterocyclic scaffold of large pharmaceutical and commercial interest associated with a plethora of biological effects and technological applications. We also demonstrate their synthetic usefulness by a photoinduced addition reaction to a polyfunctionalized amino alcohol.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.8b02402DOI Listing

Publication Analysis

Top Keywords

vinyl-124-oxadiazoles behave
4
behave nucleophilic
4
nucleophilic partners
4
partners morita-baylis-hillman
4
morita-baylis-hillman reactions
4
reactions describe
4
describe vinyl-oxadiazoles
4
vinyl-oxadiazoles function
4
function efficient
4
efficient nucleophilic
4

Similar Publications

Adjuvant chemotherapy is a well-established treatment for large-breed dogs with appendicular osteosarcoma; however, it is unclear if it improves outcomes in small-breed dogs due to limited focused studies. This retrospective study aimed to investigate the oncologic outcomes of dogs weighting less than 15 kg with appendicular osteosarcoma that underwent curative resection with or without postoperative adjuvant chemotherapy. Endpoints were time to distant progression (TTDP) and overall survival (OS).

View Article and Find Full Text PDF

Parkinson's disease (PD) is the second most common neurodegenerative disease in the world. Currently, PD is incurable, and the diagnosis of PD mainly relies on clinical manifestations. The central pathological event in PD is the abnormal aggregation and deposition of misfolded α-synuclein (α-Syn) protein aggregates in the Lewy body (LB) in affected brain areas.

View Article and Find Full Text PDF

Cytotoxic ROS-Consuming Mn(III) Synzymes: Structural Influence on Their Mechanism of Action.

Int J Mol Sci

December 2024

Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, 43124 Parma, Italy.

ROS (i.e., reactive oxygen species) scavenging is a key function of various Mn-based enzymes, including superoxide dismutases (SODs) and catalases, which are actively linked to oxidative stress-related diseases.

View Article and Find Full Text PDF

Dimer Is Not Double: The Unexpected Behavior of Two-Floor Peptide Nanosponge.

Molecules

December 2024

Department of Chemical Science and Technologies, University of Rome "Tor Vergata", Via della Ricerca Scientifica, 00133 Rome, Italy.

Using the framework of an investigation of the stimuli-responsive behavior of peptide assembly on a solid surface, this study on the behavior of a chemisorbed peptide on a gold surface was performed. The studied peptide is a dimeric form of the antimicrobial peptide Trichogin GAIV, which was also modified by substituting the glycine with lysine residues, while the N-terminus octanoyl group was replaced by a lipoic one that was able to bind to the gold surface. In this way, a chemically linked peptide assembly that is pH-responsive was obtained because of the protonation/deprotonation of the sidechains of the Lys residues.

View Article and Find Full Text PDF

Introduction: Fracture liaison services (FLS), often staffed by radiographers, identify and treat patients over the age of 50 at high risk of future fractures by intervening after the first fracture. Vertebral fragility fractures (VFF) are particularly disabling and are highly predictive of future fracture but are underdiagnosed as they often do not come to clinical attention. To review the behaviour traits of patient with opportunistically identified VFF's (OIVFF), local FLS data can be used to compare outcomes of OIVFF's with acute VFF's (AVFF) and non-hip/spine fragility fractures (NHSFF).

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!