The category of bifunctional building blocks overrides many others because of their fascinating wide applicability in synthetic chemistry. Aryl glyoxal is one of the key molecules that has been extensively used in heterocyclic chemistry to afford nearly all types of five- and six-membered heterocycles, which are the structural constituents of many natural products. The multicomponent reaction is a practical strategy to utilize this wonderful moiety with different types of starting materials to obtain numerous diverse oxygen heterocycles. This review covers the advancement of aryl glyoxal as a prime synthetic equivalent in recent years for the synthesis of oxygen heterocycles.
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http://dx.doi.org/10.1039/d2ra08315a | DOI Listing |
ACS Chem Neurosci
May 2024
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia 5756151818, Iran.
Neurodegenerative diseases (NDs) are one of the prominent health challenges facing contemporary society, and many efforts have been made to overcome and (or) control it. In this research paper, we described a practical one-pot two-step three-component reaction between 3,4-dihydronaphthalen-1(2)-one (), aryl(or heteroaryl)glyoxal monohydrates (-), and hydrazine monohydrate (NHNH•HO) for the regioselective preparation of some 3-aryl(or heteroaryl)-5,6-dihydrobenzo[]cinnoline derivatives (-). After synthesis and characterization of the mentioned cinnolines (-), the multi-targeting inhibitory properties of these heterocyclic scaffolds have been investigated upon various -type enzymes, including MAO-A, MAO-B, AChE, BChE, BACE-1, BACE-2, NQO-1, NQO-2, nNOS, iNOS, PARP-1, PARP-2, LRRK-2, GSK-3β, p38α MAPK, JNK-3, OGA, NMDA receptor, nSMase-2, IDO-1, COMT, LIMK-1, LIMK-2, RIPK-1, UCH-L1, PARK-7, and DHODH, which have confirmed their functions and roles in the neurodegenerative diseases (NDs), based on molecular docking studies, and the obtained results were compared with a wide range of approved drugs and well-known (with IC, EC, etc.
View Article and Find Full Text PDFJ Org Chem
April 2024
Department of Chemistry, Indian Institute of Technology Patna, Patna 801106, India.
Sci Rep
March 2024
Institute of Biochemistry, Heinrich Heine University Düsseldorf, Universitätsstraße 1, 40225, Düsseldorf, Germany.
Glyoxal oxidases, belonging to the group of copper radical oxidases (CROs), oxidize aldehydes to carboxylic acids, while reducing O to HO. Their activity on furan derivatives like 5-hydroxymethylfurfural (HMF) makes these enzymes promising biocatalysts for the environmentally friendly synthesis of the bioplastics precursor 2,5-furandicarboxylic acid (FDCA). However, glyoxal oxidases suffer from inactivation, which requires the identification of suitable redox activators for efficient substrate conversion.
View Article and Find Full Text PDFOrg Biomol Chem
March 2024
Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Astana, 010000, Kazakhstan.
We report highly enantioselective synthesis of L-α-hydroxy carboxylic acids (L-αHCAs) enzymatic intramolecular Cannizzaro reaction of (hetero)aryl glyoxals in the presence of glutathione-independent human glyoxalase DJ-1. Combined with the optimized synthesis of D-αHCAs using glyoxalases I and II, this approach offers a general, scalable and operationally simple access to both enantiomers of α-hydroxy acids in moderate to excellent yields with uniformly high enantioselectivity.
View Article and Find Full Text PDFSci Rep
October 2023
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran.
In the research, the core-shell procedure synthesized a novel magnetically separable heterogeneous nanocatalyst with high stability named FeO@CPTMO@dithizone-Ni. In this method, FeO was modified as a magnetic core using surfactant (SDS) and polyethylene glycol (PEG) coating; after functionalizing the magnetic nanoparticles with 3-chloropropyl-tri-methoxysilane and dithizone, Ni metal was immobilized. The prepared catalyst was identified and specified utilizing diverse physicochemical techniques involving FT-IR, XRD, SEM, EMA, BET, ICP, EDS, TGA, Raman, and TEM.
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