title: Synthesis of 5-isoxazol-3-yl-pyrimidine nucleosides as potential antileishmanial agents.
abstract: A simple and practical procedure for the preparation of C5-(isoxazol-3-yl)-pyrimidine nucleosides through 1,3-dipolar cycloaddition of the in situ formed C5-nitrile oxide substituted pyrimidine nucleosides with various terminal alkynes is presented. Compared with literature procedures, this new method has advantageous features such as readily available and inexpensive starting materials, simple procedure without using expensive transition metal catalyst, and broad scope of substrates. By employing this method, 30 nucleoside analogues were prepared in moderate yields. Biological studies on these C5-(isoxazol-3-yl)-pyrimidine nucleosides showed that most of them exhibited significant in vitro antileishmanial activity.
authors.affiliation: Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, PR China. Electronic address: shguo@htu.cn.
authors.forename: Shenghai
authors.initials: S
authors.lastname: Guo
authors.affiliation: Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, PR China.
authors.forename: Jiliang
authors.initials: J
authors.lastname: Wang
authors.affiliation: Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, PR China.
authors.forename: Xinying
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Chimiothérapie Antiparasitaire, Faculté de Pharmacie, CNRS, UMR 8076 (BioCIS), Université Paris-Sud, 92290 Châtenay-Malabry, France.
authors.forename: Sandrine
authors.initials: S
authors.lastname: Cojean
authors.affiliation: Chimiothérapie Antiparasitaire, Faculté de Pharmacie, CNRS, UMR 8076 (BioCIS), Université Paris-Sud, 92290 Châtenay-Malabry, France.
authors.forename: Philippe M
authors.initials: PM
authors.lastname: Loiseau
authors.affiliation: Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, PR China. Electronic address: xuesen.fan@htu.cn.
authors.forename: Xuesen
authors.initials: X
authors.lastname: Fan
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D006801:Humans; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007893:Leishmania donovani / Q000187:drug effects*; D007896:Leishmaniasis / Q000188:drug therapy; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000981:Antiprotozoal Agents; D007555:Isoxazoles; D011741:Pyrimidine Nucleosides
keywords: 1,3-Dipolar cycloaddition; Antileishmanial activity; Hybrid; Isoxazole; Pyrimidine nucleoside