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

Molecules. 2019 Nov 21;24(23):4236. doi: 10.3390/molecules24234236.

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: 2-benzylidene-1-tetralone; antibacterial activity; antiproliferative activity; indazole.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Bacteria / drug effects*
  • Cell Proliferation / drug effects*
  • Drug Design*
  • Hemolysis / drug effects
  • Humans
  • Indazoles / chemistry*
  • Neoplasms / drug therapy*
  • Neoplasms / pathology
  • Tumor Cells, Cultured

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Indazoles