Oxidation of cyanobenzocycloheptatrienes: Synthesis,photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives |
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| Institution: | 1. A?ri ?brahim Çeçen University, Faculty of Science and Art, Department of Chemistry, 04100 Agri, Turkey;2. Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum, Turkey;3. Konya Necmettin Erbakan University, Ahmet Kele?oglu Education Faculty, Department of Chemistry, 42099 Konya, Turkey;4. Gumushane University, Vocational School of Health Services, Department of Medical Services and Techniques, 29100 Gumushane, Turkey;5. King Saud University, Department Zoology, College of Science, Saudi Arabia;6. Università degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy;1. Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy;2. Dipartimento di Scienze della Salute, “Magna Graecia” University of Catanzaro, Campus Universitario “S. Venuta”, Viale Europa Loc. Germaneto, 88100 Catanzaro, Italy;3. Pharmaceutical Chemistry and Centre of Excellence for Pharmaceutical Sciences, School of Pharmacy, North-West University, Private Bag X6001, Potchefstroom 2520, South Africa;4. Istituto di Metodologie Chimiche, Laboratorio di Risonanza Magnetica “Annalaura Segre”, CNR, via Salaria km 29.300, 00015 Monterotondo, Rome, Italy;1. Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey;2. Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd., Boston, MA 02125, USA;1. Laboratory for Organic and Bioorganic Chemistry, “Jo?ef Stefan” Institute, Jamova 39, 1000 Ljubljana, Slovenia;2. Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ve?na pot 113, 1000 Ljubljana, Slovenia;3. Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, PA, USA;1. Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey;2. East Anatolia High-Technology Application and Research Center (DAYTAM), Atatürk University, 25240 Erzurum, Turkey;3. Narman Vocational Training High School, Narman, Erzurum, Turkey |
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| Abstract: | The oxidation of some cyanocycloheptatrienes with CrO3 and pyridine was investigated and a few new nitrile functionalised benzotropone derivatives were obtained. Photooxygenation reaction of these products was also studied. The structures of the formed products were determined on the basis of NMR spectroscopy and the formation mechanism of unusual products was discussed. Human carbonic anhydrase isoenzymes I, and II (hCA I and hCA II) inhibition properties of nitrile functionalized new benzotropone derivatives were also studied. Both CA isozymes were inhibited in the low micromolar range by these nitrile functionalized benzotropone analogues. The newly synthesized benzotropone derivatives showed inhibition constants in the sub-micromolar range (2.51–4.06 μM). The best hCA I inhibition was observed in 5H-benzocycloheptene-7-carbonitrile (Ki: 2.88 ± 0.86 μM). On the other hand, 5-oxo-5H-benzocycloheptatriene-7-carbonitrile showed the powerful inhibitory effect against hCA II (Ki: 2.51 ± 0.34 μM). |
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| Keywords: | Benzocycloheptatriene Benzotropone Oxidation Rearrangement Nitrile-substituted drugs Carbonic anhydrase inhibition |
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