Organic & Biomolecular Chemistry 2013-09-14

Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation.

Chen Zhang, Dao-Min Zhuang, Jia Li, Si-Yuan Chen, Xiao-Long Du, Jian-Yong Wang, Jing-Yun Li, Biao Jiang, Jian-Hua Yao

Index: Org. Biomol. Chem. 11(34) , 5621-33, (2013)

Full Text: HTML

Abstract

Diverse reactivity by coupling of substituted anilines with ethyl trifluoropyruvate was developed under microwave irradiation without catalysts to generate 3-trifluoromethyl-3-hydroxy oxindoles, aromatic hydroxy trifluoromethyl esters, and 1,2-dicarbonyl compounds in a fast and efficient manner. The plausible mechanism for obtaining different products was proposed. Furthermore, the anti-HIV activity of aromatic hydroxy trifluoromethyl esters was first reported. The best inhibitory activity against wild-type HIV-1 IIIB was exemplified by trifluoromethyloxindole 3q with an IC50 = 5.8 μM, which also displayed potential activity against Y181C mutant virus with an IC50 = 7.5 μM. More significantly, the activities of oxindoles 3q and 3r to inhibit K103N/Y181C double mutant HIV-1 reverse transcriptase (RT) are probably similar to that of the second-generation nonnucleoside inhibitor HBY 097 by docking calculation.

Related Compounds

  • Anilinium chloride
  • Pyruvic acid
  • <4-13C>Aniline-4-...
  • Aniline
  • Anilin-<1-13C>
  • Aniline-15N

Related Articles:

Multifunctional Magnetic Gd(3+) -Based Coordination Polymer Nanoparticles: Combination of Magnetic Resonance and Multispectral Optoacoustic Detections for Tumor-Targeted Imaging in vivo.

2015-11-11

[Small 11 , 5675-86, (2015)]

Polyamide nanofiltration membranes to remove aniline in aqueous solutions.

2014-01-01

[Environ. Technol. 35(9-12) , 1175-81, (2014)]

Design, synthesis, and evaluation of (E)-N-substituted benzylidene–aniline derivatives as tyrosinase inhibitors

2012-11-01

[Eur. J. Med. Chem. 57 , 383-90, (2012)]

Ugi multicomponent reaction product: the inhibitive effect on DNA oxidation depends upon the isocyanide moiety.

2013-09-06

[J. Org. Chem. 78(17) , 8696-704, (2013)]

Novel amphiphilic polymeric ionic liquid-solid phase micro-extraction membrane for the preconcentration of aniline as degradation product of azo dye Orange G under sonication by liquid chromatography-tandem mass spectrometry.

2014-07-04

[J. Chromatogr. A. 1349 , 24-9, (2014)]

More Articles...