Design, synthesis and biological evaluation of 2,4-disubstituted oxazole derivatives as potential PDE4 inhibitors

Li, Yasheng; Hu, De-Kun; Zhao, Dongsheng; Liu, Xingyu; Jin, Hongwei; Song, Gaopeng; Cui, Zi‐Ning; Zhang, Lian-Hui

doi:10.1016/j.bmc.2017.01.047

Cited by 20 publications

(2 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In general, 1,3-oxazoles are valuable compounds: these entities are widespread in natural objects, [41,42] and comprise useful scaffold for design of artificial drugs, [43][44][45][46][47][48][49] polymers, [50] and fluorescent materials. [51] In particular, 1,3-oxazoles bearing sulfonyl functionalities in the 4 th position are of particular interest due to their high pharmacological potential.…”

Section: Resultsmentioning

confidence: 99%

Gold‐Catalyzed Oxygen Transfer to Alkynylsulfones: A Diazo‐Free Route to 4‐Sulfonyl‐1,3‐Oxazoles

et al. 2022

View full text Add to dashboard Cite

The gold-catalyzed annulation of alkynylsulfones, involving pyridine N-oxides (as O-atom transfer reagents) and nitriles (as C=N synthons), comprises a diazo-free route to valuable 4-sulfonyl-1,3-oxazoles. This reaction operates under relatively mild conditions (IPrAuNTf 2 5 mol %, rt or 60 °C), and a number of functionalities was compatible (35 examples; 14-95%). In most cases, the SO 2 fragment, which is typically expulsed in the previously reported Au-catalyzed O-transfers to alkynylsulfones, retains in the heterocyclic products. The postulated reaction mechanism suggests a key role of reactive gold α-oxo carbene intermediates formed via the O-atom transfer.

show abstract

Section: Resultsmentioning

confidence: 99%

Gold‐Catalyzed Oxygen Transfer to Alkynylsulfones: A Diazo‐Free Route to 4‐Sulfonyl‐1,3‐Oxazoles

et al. 2022

View full text Add to dashboard Cite

show abstract

“…In the area of medicinal chemistry, five-membered heterocyclic compounds, especially heterocycles having more than one hetero atom, have shown a diverse range of biological activities. Among them, thiazolidinone, which bears a sulfur atom at 1-position, a nitrogen atom at 3-position and a carbonyl group at 2-, 4-, or 5-positions, has received a great deal of attention over the years since it is a significant and versatile moiety that has occupied a prominent position in medicinal chemistry [15,16,17,18,19,20,21,22,23,24]. Derivatives containing a thiazolidinone moiety have demonstrated a wide range of pharmacological properties, including anti-HIV, anti-malarial, anti-inflammatory and hypoglycaemic activities [25,26,27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking Analysis, and Carbonic Anhydrase Inhibitory Evaluations of Benzenesulfonamide Derivatives Containing Thiazolidinone

Zhang

Yin

et al. 2019

Molecules

View full text Add to dashboard Cite

To find novel human carbonic anhydrase (hCA) inhibitors, we synthesized thirteen compounds by combining thiazolidinone with benzenesulfonamide. The result of the X-ray single-crystal diffraction experiment confirmed the configuration of this class of compounds. The enzyme inhibition assays against hCA II and IX showed desirable potency profiles, as effective as the positive controls. The docking studies revealed that compounds (2) and (7) efficiently bound in the active site cavity of hCA IX by forming sufficient interactions with active site residues. The fragment of thiazolidinone played an important role in the binding of the molecules to the active site.

show abstract

Three‐Component [2+2+1] Gold(I)‐Catalyzed Oxidative Generation of Fully Substituted 1,3‐Oxazoles Involving Internal Alkynes

2019

View full text Add to dashboard Cite

Three‐component [2+2+1] gold(I)‐catalyzed reaction of internal alkynes (alkynyl esters or ‐ketones), nitriles, and 2‐chloropyridine N‐oxide led to a wide range of fully substituted 1,3‐oxazoles (32 examples; up to 92% isolated yields). Nitrile R3CN species, employed in the reaction as both reactants and solvents, comprise conventional nitriles (R3=Alk, Ar) and also push‐pull systems such as cyanamides (R3=NH2 and NAlk2) and the thiocyanate (R3=SPr). The advantages of the developed method include mild reaction conditions, high functional‐group tolerance, broad range of substituents R1/R3 along with a possibility of easy modification of COR2 or the amino group when R1=NH2.magnified image

show abstract

Design, synthesis and biological evaluation of 2,4-disubstituted oxazole derivatives as potential PDE4 inhibitors

Cited by 20 publications

References 22 publications

Gold‐Catalyzed Oxygen Transfer to Alkynylsulfones: A Diazo‐Free Route to 4‐Sulfonyl‐1,3‐Oxazoles

Gold‐Catalyzed Oxygen Transfer to Alkynylsulfones: A Diazo‐Free Route to 4‐Sulfonyl‐1,3‐Oxazoles

Synthesis, Molecular Docking Analysis, and Carbonic Anhydrase Inhibitory Evaluations of Benzenesulfonamide Derivatives Containing Thiazolidinone

Three‐Component [2+2+1] Gold(I)‐Catalyzed Oxidative Generation of Fully Substituted 1,3‐Oxazoles Involving Internal Alkynes

Contact Info

Product

Resources

About