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Vol. 26 No. 22 (2014): Vol 26 Issue 22

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Synthesis of Phenylcarbamic Acid and 2-[2-Oxo-3-(4-substituted phenylimino)-indolin-1-yl]acetohydrazide Derivatives as Promising Antifungal Agents

https://doi.org/10.14233/ajchem.2014.17566
Zainab Al Marhoon
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Ahmed Abdel-Megeed
Department of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia ; Department of Botany and Microbiology, Faculty of Agriculture, Saba Basha, Alexandria University, Alexandria, Egypt
Essam N. Sholkamy
Department of Botany and Microbiology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia ; Department of Botany and Microbiology, Faculty of Agriculture, Saba Basha, Alexandria University, Alexandria, Egypt
M. Rafiq H. Siddiqui
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia`
Ayman El-Faham
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia ; Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia 21321, Alexandria, Egypt

Corresponding Author(s) : Ahmed Abdel-Megeed

aamahmoud@ksu.edu.sa

Asian Journal of Chemistry, Vol. 26 No. 22 (2014): Vol 26 Issue 22

Abstract

Four phenylcarbamic acid methyl ester derivatives were prepared by oxidative transformation of isatin's Schiff bases (Baeyer-Villiger oxidation) under conventional heating as well as microwave irradiation. The ester derivatives were treated with hydrazine hydrate under microwave irradiation to afford the hydrazide derivatives in less reaction time and good yield. 2-(2-Oxo-3-(4-substituted phenylimino)indolin-1-yl)acetohydrazide derivatives were also prepared from isatin's Schiff bases under microwave irradiation in less reaction time and high yield and purity. The synthesized compounds exhibited promising antifungal activity particularly against the human pathogenic Candida albicans. While they did not show any activity against the Streptococcus pyogenes, Staphylococcus aureus, Salmonella typhi, Klebsiella pneumoniae, Pseudomonas aeruginosa, Aspergillus flavus and Aspergillus niger.

Keywords

Isatin Schiff bases Microwave irradiation Phenylcarbamic acid hydrazide Candida albicans Antimicrobial activity
Al Marhoon, Z., Abdel-Megeed, A., N. Sholkamy, E., Rafiq H. Siddiqui, M., & El-Faham, A. (2014). Synthesis of Phenylcarbamic Acid and 2-[2-Oxo-3-(4-substituted phenylimino)-indolin-1-yl]acetohydrazide Derivatives as Promising Antifungal Agents. Asian Journal of Chemistry, 26(22), 7665–7672. https://doi.org/10.14233/ajchem.2014.17566
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