New Imidazolidineiminothione, Imidazolidin-2-one and Imidazoquinoxaline  Derivatives: Synthesis and Evaluation of Antibacterial and Antifungal Activities.
A series of new 5-imino-4-thioxo-2-imidazolidinone derivatives3with various halogenated and alkylated aromatic substituents atN1andN3was synthesized. Imidazolidineiminothione derivatives3were prepared from the reaction ofN-arylcyanothioformamide derivatives with aryl isocyanates. These compounds were used as key synthons for the preparation of wide variety of new substituted imidazole compounds. Imine hydrolysis of3with ethanolic HCl produced the corresponding 4-thioxo-2,5-imidazolidindiones4.Condensation of3with benzophenonhydrazone furnished the corresponding 4-azine derivatives5. Monohydrazono and dihydrazono derivatives6and8were obtained upon treatment of imidazolidinone derivatives3with hydrazine hydrate. Finally, imidazolidinones3were reacted witho-phenylenediamines or pyrazol-5(4H)-ones and afforded the corresponding imidazoquinoxaline and imidazolidin-4-ylidenepyrazolone-5(4H)-one derivatives11and12,respectively. Evaluation of the antibacterial and antifungal activities for the synthesized compounds was carried out to probe their activities. Most of the tested compounds showed significant activities. The best antimicrobial activity was observed for 1-(3-ethoxyphenyl)-6-methyl-1-phenyl-1H-imidazo[4,5-b]quinoxalin-2(3H)-ones(11c)followed by 5-imino-3-(3-methoxy- phenyl)-1-phenyl-4-thioxoimidazolidin-2-one(3f).
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo,Egypt;
Yousry A
YA
Ammar
Applied Organic Chemistry Department, National Research Centre, Cairo,Egypt;; Faculty of Science and Arts, Mohail Asser, King Khalid University,Saudi Arabia;
Marwa A M Sh
MA
El-Sharief
Pharmacognosy Department, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451,Saudi Arabia;
Mostafa M
MM
Ghorab
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo,Egypt;
Yehia A
YA
Mohamed
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo,Egypt;
Ahmed
A
Ragab
Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo,Egypt.
Samir Y
SY
Abbas
N-arylcyanothioformanilides; antibacterial and antifungal activities; imidazolidineiminothiones; imidazolidinone; imidazoquinoxaline