Synthesis of certain new fused pyranopyrazole and pyranoimidazole incorporated into 8-hydroxyquinoline through a sulfonyl bridge at position 5 with evaluation of their in-vitro antimicrobial and antiviral activities | ||
| Egyptian Pharmaceutical Journal | ||
| Volume 11, Issue 2, December 2012, Pages 116-123 PDF (503.88 K) | ||
| DOI: 10.7123/01.EPJ.0000421482.33940.0b | ||
| Authors | ||
| Emad M. Kassem; Eslam R. El-Sawy; Howaida I. Abd-Alla; Adel H. Mandour; Dina Abdel-Mogeed; Mounir M. El-Safty | ||
| Abstract | ||
| Background and objectives Heterocyclic systems with a quinoline nucleus display a wide spectrum of biological activities such as antimicrobial and antiviral activities. The aim of the present study was the synthesis of new fused pyranopyrazoles, and , and pyranoimidazoles, and , incorporated to 8-hydroxyquinoline through a sulfonyl bridge at position 5 and evaluation of their antimicrobial and antiviral activities. Methods The synthesis of the titled quinoline derivatives was achieved through cyclization of 8-hydroxyquinoline-5-sulfonyl chloride () with 2º-acetyl-2-cyanoacetohydrazide, 2-cyanoacetic acid hydrazide, and 3-amino-5-pyrazolone to afford , , and , respectively. Moreover, reaction of with glycine gives , which on heterocyclization with ammonium thiocyanate yielded the 2-thioxoimidazolidin-2-one derivative . Cyclocondensation reaction of , , , and with different arylidene malononitriles afforded fused systems, , , , and , respectively. The synthesized compounds were evaluated for their in-vitro antimicrobial activity using the disc diffusion method. In addition, they were evaluated for their in-vitro antiviral activity against avian paramyxovirus type 1 (APMV-1) and laryngotracheitis virus (LTV). Results and conclusion In-vitro antimicrobial activity of the newly synthesized compounds included an inhibitory effect toward the growth of and (Gram-negative bacteria). Furthermore, of the six selected compounds (, , , , and ) tested for their antiviral activity, compounds , , and at a concentration range of 3–4 µg/ml showed marked viral inhibitory activity for APMV-1 of 5000 tissue culture infected dose fifty (TCID) and LTV of 500 TCID in Vero cell cultures on the basis of their cytopathic effect. Chicken embryo experiments show that compounds , , and possess high antiviral activity , with inhibitory concentration fifty (IC) ranging from 3 to 4 µg/egg against avian APMV-1 and LTV and toxic concentration fifty (CC) ranging from 200 to 300 µg/egg. | ||
| Keywords | ||
| Antimicrobial; Antiviral activities; 8-hydroxyquinoline-5-sulfonyl chloride; pyrano[2,3-] pyrazole; pyrano[2,3-]imidazole | ||
|
Statistics Article View: 38 PDF Download: 34 |
||
