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Palladium(II)-Catalyzed Reaction of Lawsones and Propargyl Carbonates: Construction of 2,3-Furanonaphthoquinones and Evaluation as Potential Indoleamine 2,3-Dioxygenase Inhibitors.
Feng, Xi; Qiu, Xiaqiu; Huang, Huidan; Wang, Jubo; Xu, Xi; Xu, Pengfei; Ge, Ruijia; Liu, Xiaojin; Li, Zhiyu; Bian, Jinlei.
Affiliation
  • Feng X; State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Design and Optimization , China Pharmaceutical University , Nanjing 210009 , China.
  • Qiu X; Department of Medicinal Chemistry, School of Pharmacy , China Pharmaceutical University , Nanjing 210009 , China.
  • Huang H; State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Design and Optimization , China Pharmaceutical University , Nanjing 210009 , China.
  • Wang J; Department of Medicinal Chemistry, School of Pharmacy , China Pharmaceutical University , Nanjing 210009 , China.
  • Xu X; Department of Pharmaceutical Engineering , China Pharmaceutical University , Nanjing 210009 , China.
  • Xu P; State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Design and Optimization , China Pharmaceutical University , Nanjing 210009 , China.
  • Ge R; Department of Medicinal Chemistry, School of Pharmacy , China Pharmaceutical University , Nanjing 210009 , China.
  • Liu X; State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Design and Optimization , China Pharmaceutical University , Nanjing 210009 , China.
  • Li Z; Department of Medicinal Chemistry, School of Pharmacy , China Pharmaceutical University , Nanjing 210009 , China.
  • Bian J; State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Design and Optimization , China Pharmaceutical University , Nanjing 210009 , China.
J Org Chem ; 83(15): 8003-8010, 2018 08 03.
Article in En | MEDLINE | ID: mdl-29882670
An efficient reaction utilizing propargyl carbonates through Claisen rearrangement to synthesize furanonaphthoquinones is described. The remarkable transformation exhibits excellent functional group tolerance, affording the target furanonaphthoquinones in moderate to good yields (41-85%) under mild reaction conditions. Scaled-up preparation of the model product can make this reaction a method of choice for synthesis of furanonaphthoquinone derivatives. The resulting furanonaphthoquinones were evaluated as potential indoleamine 2,3-dioxygenase inhibitors in vitro.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Palladium / Quinones / Carbonates / Naphthoquinones / Indoleamine-Pyrrole 2,3,-Dioxygenase Limits: Humans Language: En Journal: J Org Chem Year: 2018 Type: Article Affiliation country: China
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Palladium / Quinones / Carbonates / Naphthoquinones / Indoleamine-Pyrrole 2,3,-Dioxygenase Limits: Humans Language: En Journal: J Org Chem Year: 2018 Type: Article Affiliation country: China