Synthesis and antitumor activity of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group

A series of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group were synthesized by successively nucleophilic substitutions of 5′-deoxy-5′-amino-ribonucleosides with 2,4-dichloropyrimidine and then with various fatty amines under microwave irradiation. Their anticancer activitie...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2011-02, Vol.21 (3), p.916-919
Hauptverfasser:	Wang, Kerang, Wu, Ling, Qin, Zhanbin, Yan, Xinhao, Li, Xiaoliu, Chen, Hua, Zhang, Pingzhu, Zhang, Jinchao
Format:	Artikel
Sprache:	eng
Schlagworte:	amines Anticancer anticarcinogenic activity Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antitumor activity Biological and medical sciences Cell Line, Tumor Drug Screening Assays, Antitumor Fatty amine General aspects Humans inhibitory concentration 50 irradiation Medical sciences Microwaves Nucleophilic substitution Pharmacology. Drug treatments Pyrimidine Pyrimidines - chemistry Ribonucleoside ribonucleosides Ribonucleosides - chemical synthesis Ribonucleosides - chemistry Ribonucleosides - pharmacology
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Zusammenfassung:	A series of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group were synthesized by successively nucleophilic substitutions of 5′-deoxy-5′-amino-ribonucleosides with 2,4-dichloropyrimidine and then with various fatty amines under microwave irradiation. Their anticancer activities in vitro were preliminarily evaluated. Compounds 7a and 8a only exhibited anticancer activity against A549 cell line with the IC 50 values of 10.73 and 10.99 μM, respectively. In addition, 7h and 8h showed potent activities against both A549 and Hela cell lines with the IC 50 values of 12.71, 8.55 and 8.44, 5.55 μM, respectively.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2010.12.069