Synthesis and biological evaluation of 3-hydroxymethyl-5-(1H-1,2,3-triazol) isoxazolidines

被引：29

作者：

Romeo, Roberto ^{[1
]}

Giofre, Salvatore V. ^{[1
]}

Carnovale, Caterina ^{[1
]}

Campisi, Agata ^{[2
]}

Parenti, Rosalba ^{[3
]}

Bandini, Lorenzo ^{[4
]}

Chiacchio, Maria A. ^{[2
]}

机构：

[1] Dipartimento Sci Farmaco & Prodotti Salute, I-98168 Messina, Italy

[2] Dipartimento Sci Farmaco, I-95125 Catania, Italy

[3] Dipartimento Sci Biomed, Sez Fisiol, I-95125 Catania, Italy

[4] Ist Igiene Sanita Pubbl, Dipartimento GF Ingrassia, I-95123 Catania, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2013年 / 21卷 / 24期

关键词：

Modified nucleosides; Click-chemistry; Antitumor agents; 1,3-Dipolar cycloaddition; FTC-133 and 8305C cell lines; PHOSPHONATED CARBOCYCLIC 2'-OXA-3'-AZANUCLEOSIDES; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; TISSUE TRANSGLUTAMINASE; ANTIVIRAL ACTIVITY; ANALOGS; NUCLEOSIDES; CULTURES; NITRONE; DESIGN;

D O I：

10.1016/j.bmc.2013.10.001

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A synthetic approach towards a series of 3-hydroxymethyl-5-(1H-1,2,3-triazol) isoxazolidines has been reported, according to a procedure based on the cycloaddition reaction, under microwave irradiation, of a nitrone with 1-vinyl triazoles, prepared by a click reaction of azides with alkynes. Biological tests show that the synthesized compounds are able to inhibit proliferation of follicular and anaplastic human thyroid cancer cell lines, with IC50 values ranging from 3.87 to 8.76 mu M. The obtained compounds induce caspase-3 activation and DNA fragmentation prevalently in follicular human thyroid cancer cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：7929 / 7937

页数：9

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