Parallel synthesis of novel antitumor agents: 1,2,3-triazoles bearing biologically active sulfonamide moiety and their 3D-QSAR

College of Pharmaceutical Science, Zijin Campus, Zhejiang University, Hangzhou 310058, People's Republic of China.
Molecular Diversity (Impact Factor: 1.9). 07/2011; 15(4):927-46. DOI: 10.1007/s11030-011-9324-3
Source: PubMed


A 60-member 1,2,3-triazoles bearing biologically active sulfonamide moiety library was synthesized via azide-alkyne cycloaddition and examined for cytotoxic activity against human leukemia cell line HL-60. 25 of them were evaluated further in four additional cancer cell lines (HepG2, A549, PC3, SGC7901). Most of the 25 compounds showed moderate cytotoxic activities against the tested cell lines. Furthermore, the structure-activity relationships were discussed and a reliable 3D-QSAR model with good prediction (r²cv = 0.64, r² = 0.958) was generated on the basis of our synthesized 1,2,3-triazoles for their cytotoxic activities against the HL-60 cell line. The contour map of the CoMFA should aid in the design of new antitumor agents.

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    • "Moreover, some compounds have better pharmacological profiles such as oral absorption with low side effects. Furthermore, triazoles bearing sulfonamide moiety have been reported to exert antimicrobial (Ezabadi et al., 2008; Faidallah et al., 2011; Thomas et al., 2011; Wang et al., 2010; Wilkinson et al., 2007), antimalarial (Boechat et al., 2011), and antitumor (Ou et al., 2011) activities. "
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    ABSTRACT: A new series of 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide derivatives 5 were synthesized through the Click approach and evaluated for their cytotoxic activity against four cancer cell lines (HuCCA-1, HepG2, A549, and MOLT-3). Most of the synthesized triazoles 5 displayed cytotoxicity against MOLT-3 cell line, except for analogs 5a–c and 5e. Significantly, 4-phenyltriazoles (5a and 5n), 4-(naphthalen-2-yloxy)methyltriazole 5d, as well as 4-((2-oxo-2H-chromen-7-yl)oxy)methyltriazole 5l showed higher cytotoxic activity against HepG2 cells than the reference drug, etoposide. Interestingly, the 4-phenyltriazole 5a was the most potent and promising compound with IC50 value of 9.07 μM against HepG2 cell line. The analog 5a also exerted the highest cytotoxic activity against HuCCA-1 cells. This finding provides the novel lead molecules for further development.
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