Synthesis and in vitro anticancer activity of pyrazolo[1, 5-a]pyrimidines and pyrazolo[3, 4-d][1, 2, 3]triazines. Issue 21 (2nd November 2017)

• Record Type: Journal Article
• Authors: Hassan, Ashraf S.; Moustafa, Gaber O.; Awad, Hanem M.
• Is Part Of: Synthetic communications. Volume 47:Issue 21(2017)
• Page Start: 1963
• Page End: 1972
• Publication Date: 2017-11-02
• Subjects: 5-Aminopyrazole -- anticancer activity -- fused pyrazoles -- pyrazolo[1, 5-a]pyrimidines -- pyrazolo[1, 5-a]quinazolines -- pyrazolo[3, 4-d]triazines; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2017.1358368
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: A novel series of pyrazolo[1, 5- a ]pyrimidines14a–j and pyrazolo[1, 5- a ]quinazolines18a, b were synthesized via condensation of 5-amino-1 H -pyrazoles10a, b with 3-(dimethylamino)-1-aryl-prop-2-en-1-ones11a–e and 2-((dimethylamino)methylene)-5, 5-dimethylcyclohexane-1, 3-dione (15 ), respectively, in glacial acetic acid. Finally, treatment of10a, b with sodium nitrite (NaNO2 ) afforded pyrazolo[3, 4- d ]triazines20a, 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-2 H -tetrazolium bromide (MTT) assay. The results reveal that, the compounds14b and14h were the most potent in comparison with doxorubicin. The structure–activity relationship was discussed. GRAPHICAL ABSTRACT: