title: Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives.
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 (2.51-4.06μM). The best hCA I inhibition was observed in 5H-benzocycloheptene-7-carbonitrile (Ki: 2.88±0.86μM). On the other hand, 5-oxo-5H-benzocycloheptatriene-7-carbonitrile showed the powerful inhibitory effect against hCA II (Ki: 2.51±0.34μM).
authors.affiliation: Ağri İbrahim Çeçen University, Faculty of Science and Art, Department of Chemistry, 04100 Agri, Turkey; Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum, Turkey. Electronic address: mguney@atauni.edu.tr.
authors.forename: Murat
authors.initials: M
authors.lastname: Güney
authors.affiliation: Konya Necmettin Erbakan University, Ahmet Keleşoglu Education Faculty, Department of Chemistry, 42099 Konya, Turkey. Electronic address: acoskun@konya.edu.tr.
authors.forename: Ahmet
authors.initials: A
authors.lastname: Coşkun
authors.affiliation: Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum, Turkey; Gumushane University, Vocational School of Health Services, Department of Medical Services and Techniques, 29100 Gumushane, Turkey.
authors.forename: Fevzi
authors.initials: F
authors.lastname: Topal
authors.affiliation: Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum, Turkey.
authors.forename: Arif
authors.initials: A
authors.lastname: Daştan
authors.affiliation: Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum, Turkey; King Saud University, Department Zoology, College of Science, Saudi Arabia. Electronic address: igulcin@atauni.edu.tr.
authors.forename: Ilhami
authors.initials: I
authors.lastname: Gülçin
authors.affiliation: Università degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy. Electronic address: claudiu.supuran@unifi.it.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors* / Q000378:metabolism; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors* / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D013329:Structure-Activity Relationship; D014334:Tropolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D002257:Carbonic Anhydrase Inhibitors; D007527:Isoenzymes; D014334:Tropolone; C003730:tropone; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II
keywords: Benzocycloheptatriene; Benzotropone; Carbonic anhydrase inhibition; Nitrile-substituted drugs; Oxidation; Rearrangement