Synthesis, Spectral, Anti-Liver Cancer and Free Radical Scavenging Activity of New Azabicyclic Thienoyl Hydrazone Derivatives

M. Manimaran¹, A. Ganapathi^2*, T. Balasankar²

¹Department of Chemistry, Annamalai University, Annamalai Nagar, India.
²Chemistry Section, FEAT, Annamalai University, Annamalai Nagar, India.

DOI: 10.4236/ojmc.2015.53004                

Abstract

To exploit the potential biological activities of azabicyclic based, seven 2r, 4c-diaryl-3-azabicyclo [3.3.1] nonan-9-one-2’-thienoyl hydrazone were synthesized. The structural elucidation and stereochemistry of these compound assigned by FT-IR, ¹H, ¹³C and 2D NMR spectral data. The Structural Activity Relationship (SAR) of the target compounds were examined for their in vitro anti-proliferative, antioxidant and antimicrobial activities. The initial screen was treated against human liver cancer cell lines (HepG2) with IC₅₀ values determined by MTT assay. Fluoro substitution at para position of phenyl ring compound 12 showed more antiproliferative activity against HepG2 at half maximum inhibitory concentration (IC₅₀ = 3.76 μg/mL) than other target hydrazones. The mechanism of the antitumor action of active compound 12 was investigated through Hoechst stain 33342 analyses. It indicated that the compound inhibited HepG2 cancer cells proliferation by triggering apoptotic cell death. The Free radical scavenging activity of all synthesized compounds were evaluated with , and radicals. The compounds 11 (IC₅₀ rang 3.78 - 4.31 μg/mL) and 15 (IC₅₀ rang 4.61 - 5.16 μg/mL) were exhibited higher free radical scavenging activity than standard BHT drug. Besides, all the target compounds were screened for their in vitro antibacterial and antifungal activity against a spectrum of microbial organisms by using twofold dilution method. These studies proved that halogen substituted compounds 12, 13 and 14 were showed excellent inhibitory potency at lowest minimum inhibitory concentration (MIC) range of 6.25 - 25.5 μg/mL. Nevertheless, multiple mechanisms regulating the antioxidant and anticancer effects of the hybrid molecules need to be further investigations.

Keywords

2-Thienoyl Hydrzones, Antioxidant, Anticancer, Cytotoxicity, Antimicrobial Activity

Conflicts of Interest

The authors declare no conflicts of interest.

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