Synthesis and in vitro anticancer activity of pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-d][1,2,3]triazines

被引：60
|
作者：
Hassan, Ashraf S. [1 ]
Moustafa, Gaber O. [2 ]
Awad, Hanem M. [3 ]
机构：
[1] Natl Res Ctr, Dept Organometall & Organometalloid Chem, Cairo 12622, Egypt
[2] Natl Res Ctr, Dept Peptide Chem, Cairo, Egypt
[3] Natl Res Ctr, Dept Tanning Mat & Leather Technol, Cairo, Egypt
来源：
SYNTHETIC COMMUNICATIONS | 2017年 / 47卷 / 21期
关键词：
5-Aminopyrazole; anticancer activity; fused pyrazoles; pyrazolo[1; 5-a]pyrimidines; 5-a]quinazolines; pyrazolo[3,4-d]triazines; ANTIMICROBIAL ACTIVITY; BIOLOGICAL EVALUATION; ANTITUMOR-ACTIVITY; SCHIFF-BASES; DERIVATIVES; CYTOTOXICITY; PYRAZOLOPYRIMIDINES; MOIETY; THIOGLYCOSIDES; ANTIOXIDANT;
D O I：
10.1080/00397911.2017.1358368
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel series of pyrazolo[1,5-a]pyrimidines 14a-j and pyrazolo[1,5-a]quinazolines 18a, b were synthesized via condensation of 5-amino-1H-pyrazoles 10a, b with 3-(dimethylamino)-1-aryl-prop-2-en-1-ones 11a-e and 2-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione (15), respectively, in glacial acetic acid. Finally, treatment of 10a, b with sodium nitrite (NaNO2) afforded pyrazolo[3,4-d]triazines 20a, b. Structures of compounds were confirmed by their spectral data. These compounds were screened for their in vitro cytotoxic activities against human cancer cell lines (HepG-2 and MCF-7) using 3-[4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. The results reveal that, the compounds 14b and 14h were the most potent in comparison with doxorubicin. The structure-activity relationship was discussed.
引用
收藏
页码：1963 / 1972
页数：10
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