title: Synthesis, characterization, anticancer, antimicrobial and carbonic anhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives.
abstract: In the present study, a series of new hybrid compounds containing chalcone and methanoisoindole units 7a-n ((3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione) were synthesized, characterized and investigated for their anticancer activity against C6 gliocarcinoma cell in rats, and antimicrobial activity against some human pathogen microorganisms. The compounds 7e, 7h, 7j, 7k, 7L and 7n showed very high anticancer activity with the inhibition range of 80.51-97.02% compared to 5-FU. Some of the compounds exhibited anti-microbial activity. Also, they evaluated for inhibition effects against human carbonic anhydrase I, and II isoenzymes (hCA I and II) with Ki values in the range of 405.26-635.68pM for hCA I, and 245.40-489.60pM for hCA II, respectively. These results demonstrated that 3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl)phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives could be used in different biomedical applications.
authors.affiliation: Cumhuriyet University, Vocational School of Health Services, 58140 Sivas, Turkey. Electronic address: ukocyigit@cumhuriyet.edu.tr.
authors.forename: Umit M
authors.initials: UM
authors.lastname: Kocyigit
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey. Electronic address: yakup.budak@gop.edu.tr.
authors.forename: Yakup
authors.initials: Y
authors.lastname: Budak
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey.
authors.forename: Meliha Burcu
authors.initials: MB
authors.lastname: Gürdere
authors.affiliation: Department of Molecular Biology and Genetics, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey.
authors.forename: Şaban
authors.initials: Ş
authors.lastname: Tekin
authors.affiliation: Department of Molecular Biology and Genetics, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey.
authors.forename: Tuğba Kul
authors.initials: TK
authors.lastname: Köprülü
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey.
authors.forename: Fatih
authors.initials: F
authors.lastname: Ertürk
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey.
authors.forename: Kezban
authors.initials: K
authors.lastname: Özcan
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey; Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia.
authors.forename: İlhami
authors.initials: İ
authors.lastname: Gülçin
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey.
authors.forename: Mustafa
authors.initials: M
authors.lastname: Ceylan
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002599:Chalcone / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D006801:Humans; D054833:Isoindoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D009181:Mycoses / Q000188:drug therapy; D009369:Neoplasms / Q000188:drug therapy; D051381:Rats; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D002257:Carbonic Anhydrase Inhibitors; D054833:Isoindoles; D002599:Chalcone; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II
keywords: Anticancer; Antimicrobial; C6; Carbonic anhydrase; Chalcone; Isoindole