title: Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation.
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.
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. zhangchen@mail.sioc.ac.cn
authors.forename: Chen
authors.initials: C
authors.lastname: Zhang
authors.forename: Dao-Min
authors.initials: DM
authors.lastname: Zhuang
authors.forename: Jia
authors.initials: J
authors.lastname: Li
authors.forename: Si-Yuan
authors.initials: SY
authors.lastname: Chen
authors.forename: Xiao-Long
authors.initials: XL
authors.lastname: Du
authors.forename: Jian-Yong
authors.initials: JY
authors.lastname: Wang
authors.forename: Jing-Yun
authors.initials: JY
authors.lastname: Li
authors.forename: Biao
authors.initials: B
authors.lastname: Jiang
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Yao
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry / Q000494:pharmacology*; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D004305:Dose-Response Relationship, Drug; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors* / Q000235:genetics / Q000378:metabolism; D015497:HIV-1 / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D008958:Models, Molecular; D015394:Molecular Structure; D009154:Mutation; D019289:Pyruvic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000814:Aniline Compounds; D019380:Anti-HIV Agents; D018894:Reverse Transcriptase Inhibitors; C513102:ethyl trifluoropyruvate; D019289:Pyruvic Acid; C514824:reverse transcriptase, Human immunodeficiency virus 1; D054303:HIV Reverse Transcriptase; C023650:aniline