Synthesis of Indolo[3,2-b]carbazoles via an Anomeric-Based Oxidation Process: A Combined Experimental and Computational Strategy

NoIndolo[3,2-b]carbazole is a molecule of great biological significance, as it is formed in vivo after consumption of cruciferous vegetables. The reaction of 1H-indole and various aldehydes in the presence of a catalytic amount of N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide as an efficient and homogeneous catalyst in acetonitrile at 50°C produces 6,12-disubstituted 5,7-dihydroindolo[2,3-b]carbazole with an in good to excellent yield. The presented technique offers a fast and robust method, by the use of inexpensive commercially available starting materials toward 6,12- disubstituted 5,7-dihydroindolo[2,3-b]carbazole. A new anomeric-based oxidation was kept in mind for the final step of the indolo[2,3-b]carbazoles synthesis. The suggested anomeric-based oxidation mechanism was supported by experimental and theoretical evidences.The Grant of Allameh Tabataba’i’s Award, Grant Number: BN09

Study on antibacterial activity of newly synthesized derivatives of pyranopyrazole, pyrazolo[1,2-b]phtalazine and bis-pyrazole

<p>In recent years, due to a sharp increase of antibiotic resistance, synthesized derivative compounds have been considered as a superseded source for new drugs. With regard to the high therapeutic behavior of isatin derivatives from many aspects of drug discovery, in this study, the antibacterial effects of newly synthesized derivatives of pyranopyrazole, pyrazolo[1,2-b]phtalazine and bis-pyrazole against Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Enterococcus faecalis were examined.</p><p>Twelve individual compounds were weighted and prepared at a final concentration of 1 mg/mL in dimethyl sulfoxide (DMSO). Bacterial test organisms were maintained in nutrient agar slants at 4ºC and subcultured in Petri plates prior to use. The tested compounds are randomly added into the wells with a 100 μl volume on the plate under sterile condition and then were incubated at 37ºC for 24 hours. All experiments were repeated three times and the mean values are reported as the results. The antibacterial effects of the compounds that produced ≥ 8mm zone of inhibition were tested quantitatively by Micro broth dilution method for determination of minimal inhibitory concentration (MIC) value. After incubation overnight, the first tube with clean appearance determined the MIC.</p><p>According to the results, the MIC of the compounds defined as c and d against S. aureus is 64 (μg/ml). It is found that the synthesized compounds are only effective against S. aureus.</p><p>The comparison of the maximum zone of inhibition (22±0.4) and MICs between the present study and those in literature, shows the privilege of using compound c and d against S. aureus.</p&gt