Synthesis, Characterization and Investigation of the Biological Activities of Certain Adamantane-1-Carbohydrazide Hydrazones

Tez Türü: Yüksek Lisans

Tezin Yürütüldüğü Kurum: Omdurman Islamic University, Pharmacy, Pharmaceutical chemistry, Sudan

Tez Danışmanı: Dr. Tilal Elsaman

Tezin Onay Tarihi: 2018

Tezin Dili: İngilizce

Özet:

Study objectives: To synthesize, characterize and investigate the biological activities of certain admantane-1-carbohydrazide hydrazones.

Methods: Schiff’s condensation reaction was employed to synthesize fifteen Schiff base compounds (H1-H15) by reacting equimolar quantities of appropriate isatin and adamantane-1-carbohydrazide. The products were purified by recrystallization and their respective chemical structures were deduced using various spectral tools (IR, MS, ¹H NMR and ¹³C NMR). The synthesized compounds (H1, H2, H4, H5, H13 and H14) were investigated against (70mg/kg) pentylenetetrazole-induced seizure model. All synthesized compounds (H1-H15) were evaluated against influenza A H1N1 virus by hemagglutination inhibition assay.

Results: Most of biologically tested compounds exhibited protection activities against pentylenetetrazole-induced seizure model. Interestingly compound H13 showed the highest seizure protection (67%) when compared to standard phenobarbital 30mg/kg (25% inhibition). All synthesized compounds increased the latency of convulsion and decrease the duration of seizure in comparison to the negative control. Compounds (H1-H15) were found to be active against influenza A virus and showed positive hemagglutination inhibition in safe concentrations. All compounds showed low docking energies than standard drug phenobarbital and amantidine when docked into GABA_A and influenza matrix protein 2, respectively.

Conclusion: All synthesized compounds are active against influenza A virus and represent a good candidate of newer anti-influenza virus drugs. H13 was found to be the most active compound against pentylenetetrazole-induced convulsion. The compounds could be envisioned as a promising and potential lead compound for drug discovery projects.