Synthesis,Characterization and Evaluation of the Anticancer and Antimicrobial Activities of Some Novel Benzazole and Benzazine Derivatives

Naglaa Z.H Eleiwa,Samar.M Mouneir,Wesam Saber Shehab

doi:10.24297/jac.v3i3.927

Naglaa Z.H Eleiwa, Samar.M Mouneir + Show 1 more

Open Access

https://doi.org/10.24297/jac.v3i3.927

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Abstract

The present study was designed to synthesize and develop new useful lead compounds (some novel benzazole and benzazine derivatives ) of simple structure , exhibiting optimal in vitro anticancer and antimicrobial potency. Phenylenediamine derivative 1 was condensed with dithiocarboxylic acid derivatives 2 and produced benzimidazole derivative 4. The benzotriazepines 8 and 10 were formed by the reaction of 1 with dicarbonyl derivatives followed by intermolecular coupling reaction. The synthesis of benzotriazine12, benzotriazole 14,17, benzimidazole16 and benzothiadiazine 19 from compound 1 was also described. The Synthesized Compounds were characterized by Spectral Studies like IR, H1 – NMR and Analysis Spectra .The title compounds were screened for their possible In vitro anticancer and antimicrobial activities. Among the synthesized compounds, some have shown promisingly remarkable activities against different cancer cell lines (MCF-7 human breast cancer cells, HepG2 human hepatocarcinoma cells and PC3 human prostate cancer cells)and moderate to high antibacterial and antifungal activities. The obtained results showed that the most active compounds could be useful as a template for future design, modification and investigation to produce more active analogs.

Highlights

Cancer is a broad term used to encompass several malignant diseases. It defined as the uncontrolled and undifferentiated growth of abnormal cells that can affect every organ in the body and sometimes forming excess tissue known as tumor
O-phenylenediamine seemed of suitable located functionally for further heterocyclization giving benzazoles and benzazines, the fusion of imidazole to benzene ring was achieved by one pot procedure via refluxing ophenylenediamine derivative and dithiocarboxylic acid derivatives
The synthetic strategy toward the desired benzotriazepines depended on the condensation of o-phenylenediamine derivative 1 with dicarbonyl compound followed by diazotization and subsequent intramolecular coupling afforded the final benzazepine compounds. condensation of compound 1 and acetylacetone gave the enaminic product 5 that undergo intramolecular heterocyclization via diazotization through the coupling of electrophilic nitrogen to the nucleophilic carbon

Summary

1.INTRODUCTION

Cancer is a broad term used to encompass several malignant diseases. It defined as the uncontrolled and undifferentiated growth of abnormal cells that can affect every organ in the body and sometimes forming excess tissue known as tumor. The reaction mixture was further stirred for 1 hour, and the separated solid product was filtered off, washed with water, dried and crystallized from toluene and gave compound 7. The reaction mixture was further stirred for 1 hour, and the separated solid product was filtered off, washed with water, dried and crystallized from benzene and gave compound 10. Further the depth of the agar in the plate is a factor to be considered in the disc diffusion method This method is well documented and standard zones of inhibition have been determined for susceptible and resistant values.Blank paper disks (Schleicher & Schuell, Spain) with a diameter of 8.0 mm were impregnated 10μ of tested concentration of the stock solutions. Agar-based methods such as Etest and disk diffusion can be good alternatives because they are simpler and faster than broth-based methods [22,23]

3.RESULTS and Discussion

C N Ph N H

4.CONCLUSION

5.REFERENCES