Synthesis and biological evaluation of novel flavone/triazole/benzimidazole hybrids and flavone/isoxazole-annulated heterocycles as antiproliferative and antimycobacterial agents

Mol Divers. 2018 Nov;22(4):803-814. doi: 10.1007/s11030-018-9833-4. Epub 2018 Jun 4.

Abstract

A series of new flavone/isoxazole fused heterocycles 5a-f and flavone/1,2,3-triazole/benzimidazole hybrid heterocycles compounds 7a-t were synthesized via an intramolecular cyclization and Cu(I)-catalyzed click 1,3-dipolar cycloaddition. The products were evaluated for their antiproliferative activity against human breast cancer cell line (MCF-7) using sulforhodamine B assay (SRB) and antimycobacterial activity using turbidometric assay. The majority of the tested compounds exhibited antiproliferative activity and antimycobacterial activity. Compounds 7l, 7q and 7r showed moderate antiproliferative activity with IC50 values 17.9, 14.2, 19.1 [Formula: see text], respectively, and compound 5a showed moderate antimycobacterial activity with 41.7% of inhibition at 30 [Formula: see text] concentration.

Keywords: 1, 2, 3-Triazole; 8-Formyl-7-hydroxy flavones; Antimycobacterial activity; Antiproliferative activity; Click chemistry; Cycloaddition.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Cell Proliferation / drug effects
  • Chemistry Techniques, Synthetic
  • Flavones / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Isoxazoles / pharmacology*
  • MCF-7 Cells
  • Microbial Sensitivity Tests
  • Triazoles / chemistry*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Benzimidazoles
  • Flavones
  • Isoxazoles
  • Triazoles