Synthesis of 5-isoxazol-3-yl-pyrimidine nucleosides as potential antileishmanial agents. 2015

Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
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.

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.

UI MeSH Term Description Entries
D007555 Isoxazoles Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions. Isoxazole
D007893 Leishmania donovani A parasitic hemoflagellate of the subgenus Leishmania leishmania that infects man and animals and causes visceral leishmaniasis (LEISHMANIASIS, VISCERAL). The sandfly genera Phlebotomus and Lutzomyia are the vectors. Leishmania (Leishmania) donovani,Leishmania leishmania donovani,Leishmania donovanus,Leishmania leishmania donovanus,donovani, Leishmania leishmania,donovanus, Leishmania,donovanus, Leishmania leishmania,leishmania donovanus, Leishmania
D007896 Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL). Leishmania Infection,Infection, Leishmania,Infections, Leishmania,Leishmania Infections,Leishmaniases
D011741 Pyrimidine Nucleosides Pyrimidines with a RIBOSE attached that can be phosphorylated to PYRIMIDINE NUCLEOTIDES. Nucleosides, Pyrimidine
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000981 Antiprotozoal Agents Substances that are destructive to protozoans. Schizonticides,Agents, Antiprotozoal
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs

Related Publications

Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
May 1998, Bioorganic & medicinal chemistry letters,
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
June 1973, Chemical & pharmaceutical bulletin,
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
December 1992, The Journal of antibiotics,
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
February 2010, Acta crystallographica. Section E, Structure reports online,
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
April 1999, Die Pharmazie,
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
April 2000, Nucleosides, nucleotides & nucleic acids,
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
April 2021, Journal of medicinal chemistry,
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
March 2014, Bioorganic & medicinal chemistry letters,
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
November 1990, Farmaco (Societa chimica italiana : 1989),
Shenghai Guo, and Jiliang Wang, and Xinying Zhang, and Sandrine Cojean, and Philippe M Loiseau, and Xuesen Fan
July 2008, Archives of pharmacal research,
Copied contents to your clipboard!