Design and Synthesis of New 6-Nitro and 6-Amino-3,3a,4,5-Tetrahydro-2<i>H</i>-Benzo[<i>g</i>]indazole Derivatives: Antiproliferative and Antibacterial Activity

Abstract

New substituted benzo[g]indazoles functionalized with a 6-nitro and 6-amino groups have been synthesized by the reaction of benzylidene tetralones with hydrazine in acetic acid. The resulting conformationally-constrained compounds were evaluated for their antiproliferative activity against selected cancer cell lines. The nitro-based indazoles 11a, 11b, 12a and 12b have shown IC50 values between 5−15 μM against the lung carcinoma cell line NCI-H460. Moreover, the nitro compounds were tested for antibacterial activity where compounds 12a and 13b have shown MIC values of 250 and 62.5 μg/mL against N. gonorrhoeae with no hemolytic activity in human red blood cells (RBC).

Keywords

• indazole
• 2-benzylidene-1-tetralone
• antiproliferative activity
• antibacterial activity