Transition-metal-free synthesis of oxazoles: valuable structural fragments in drug discovery

Ibrar, Aliya; Khan, Imtiaz; Abbas, Naeem; Farooq, Umar; Khan, Ajmal

doi:10.1039/c6ra19324b

Cited by 81 publications

(47 citation statements)

References 161 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A five‐membered heterocyclic aromatic ring compound, oxazole is one of the important platform having in a wide variation of biologically active compounds and natural products . In current years, its research has increase considerable attention from both industry and academia in view of its assorted pharmacological properties . Some oxazoles showed inhibitory activity of enzyme as well as against nitric oxide (NO) production in lipopolysaccharide (LPS)‐induced RAW 264.7 cells .…”

Section: Introductionmentioning

confidence: 99%

“…Some oxazoles showed inhibitory activity of enzyme as well as against nitric oxide (NO) production in lipopolysaccharide (LPS)‐induced RAW 264.7 cells . The reports available on substituted oxazoles can be used as agrochemicals, fluorescent dyes, corrosion inhibitors and find applications in photography and polymer industries . In addition, they can assist as significant rout in organic synthesis .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Fluorescence Spectroscopic Studies on the Interaction Between 2,5‐Diphenyl Oxazole and Triton X‐100 Micelle

Patil

Salunkhe²,

Mahanwar

et al. 2019

Macromolecular Symposia

View full text Add to dashboard Cite

The interaction between Triton X‐100 (TX‐100) and 2,5‐diphenyl oxazole (2,5‐DPO) has been investigated successfully by fluorescence and UV–vis study. The fluorescence resonance energy transfer (FRET) between donor TX‐100 and acceptor 2,5‐DPO was examined. UV–vis study shows that there is no formation of ground state complex between donor and acceptor pair in solution. The fluorescence emission and energy transfer efficiency has been determined in both premicellar and postmicellar condition. The distances r = 3.23 and 2.79 nm were calculated in premicellar and postmicellar solutions, respectively. The study indicates that energy transfer in postmicellar environment is remarkably higher than that in case of premicellar situation.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluorescence Spectroscopic Studies on the Interaction Between 2,5‐Diphenyl Oxazole and Triton X‐100 Micelle

Patil

Salunkhe²,

Mahanwar

et al. 2019

Macromolecular Symposia

View full text Add to dashboard Cite

show abstract

“…Some oxazoles also exhibited enzyme inhibitory activity. It is reported that substituted oxazoles can be used as agrochemicals, fluorescent dyes, corrosion inhibitors and find applications in photography and polymer industries . In addition, they can serve as important synthons in organic synthesis .…”

Section: Introductionmentioning

confidence: 99%

“…Particularly, 2,5‐substituted aryl or alkyl oxazoles are privileged scaffolds found in numerous natural products and pharmaceutical agents . They have been investigated as antidiabetic, anticancer, and antibacterial agents …”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis and In Vitro Biological Evaluation of 2,5‐Diaryloxazoles as Potential Nitric Oxide Production Inhibitors

Jang

Damodar

Kim

et al. 2017

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

An efficient first synthesis of 2,5‐diaryloxazoles 1–5 was accomplished from commercially inexpensive precursors and in overall yields of 38–48%. The synthesis proceeds via α‐aminoketones and cyclodehydration (Robinson–Gabriel reaction) as key step. Next, these oxazoles were examined for their inhibitory effect against nitric oxide (NO) production in lipopolysaccharide (LPS)‐induced RAW 264.7 cells and were found to display concentration‐dependent inhibition of NO production without cytotoxicity. Of note, compound 3 (70.7%; IC50 = 2.33 μM) was identified as a potent inhibitor in view of its comparable inhibitory effect with the positive control, N G‐monomethyl‐L‐arginine acetate (L‐NMMA) (79.3%; IC50 = 4.51 μM) followed by compounds 5 (68.3%; IC50 = 2.30 μM) and 2 (53.9%; IC50 = 6.31 μM). As a whole, compound 3 may hold great promise for further development of NO production targeted anti‐inflammatory agent.

show abstract

“…13,14 Among them, the cycloisomerization of N-propargyl amides has been widely employed as the effective and versatile synthesis of oxazoles (Scheme 3).…”

Section: -Iodane-mediated Cycloisomerization/functionalization Reactionsmentioning

confidence: 99%

Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions

Saitô¹

2017

Arkivoc

View full text Add to dashboard Cite

As a metal-free construction of oxazoles and furans concomitant with the introduction of oxygen functional groups or fluorine atoms into the side chains, we have developed λ 3 -iodane-mediated cycloisomerization/functionalization reactions of propargyl compounds. In these reactions, aryl-λ 3 -iodane ArI(X)Y works not only as a donor of heteroatomic functional groups but also as an activator of carbon-carbon triple bonds. Therefore, this methodology is not required any transition metal catalysts, which are frequently used in previous methods. Furthermore, this methodology can be extended to λ 3 -iodane-mediated [2+2+1] cycloaddition type reactions of alkynes, nitriles and heteroatoms for metal-free formation of oxazoles and imidazoles.

show abstract

Transition-metal-free synthesis of oxazoles: valuable structural fragments in drug discovery

Abstract: This review article encapsulates the recent developments in the metal-free approaches used to construct oxazole moiety.

Cited by 81 publications

References 161 publications

Fluorescence Spectroscopic Studies on the Interaction Between 2,5‐Diphenyl Oxazole and Triton X‐100 Micelle

Fluorescence Spectroscopic Studies on the Interaction Between 2,5‐Diphenyl Oxazole and Triton X‐100 Micelle

Efficient Synthesis and In Vitro Biological Evaluation of 2,5‐Diaryloxazoles as Potential Nitric Oxide Production Inhibitors

Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions

Contact Info

Product

Resources

About