title: Synthesis of 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene Derivatives and Evaluations of Their Carbonic Anhydrase Isoenzymes Inhibitory Effects.
abstract: Rearrangement of 1,6-bis(3,4-dimethoxyphenyl)hexane-1,6-dione (8) gave two isomeric products having cyclopentene moiety. Starting from the major product (3,4-dimethoxyphenyl)[2-(3,4-dimethoxyphenyl)cyclopent-1-en-1-yl]methanone (11), eight new compounds (16-23) were obtained by the reactions such as reduction (by catalytic hydrogenation and NaBH4 ), nitration, 1,4-addition, bromination, and esterification reactions. Carbonic anhydrases (CA, E.C.4.2.1.1) are ubiquitous metalloenzymes present in almost all living organism that catalyze a simple reaction, the conversion of carbon dioxide (CO2 ) and water (H2 O) to bicarbonate ion (HCO3 (-) ) and a proton (H(+) ). CA isoenzymes I and II (hCA I and II) inhibition effects of synthesized eleven new and four known compounds (8-13 and 15-23) were investigated. Inhibition studies of the hCA I and II with 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene derivatives revealed that they possess effective inhibitory potency. Cytosolic hCA I and II isoenzymes were potently inhibited by new synthesized 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene derivatives with Ki s in the range of 313.16-1537.00 nm against hCA I and in the range of 228.31-1927.31 nm against hCA II, respectively.
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey.
authors.forename: Tekin
authors.initials: T
authors.lastname: Artunç
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey.|Department of Food Technology, Oltu Vocational School, Atatürk University, Oltu-Erzurum, Turkey.
authors.forename: Yasin
authors.initials: Y
authors.lastname: Çetinkaya
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey.|Faculty of Sciences and Letters, Aǧri Ibrahim Cecen University, Aǧri, Turkey.
authors.forename: Hülya
authors.initials: H
authors.lastname: Göçer
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, 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 Science, Atatürk University, Erzurum, Turkey.
authors.forename: Abdullah
authors.initials: A
authors.lastname: Menzek
authors.affiliation: Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey.
authors.forename: Ertan
authors.initials: E
authors.lastname: Şahin
authors.affiliation: Dipartimento NEUROFARBA, Sezione di Scienze Farmaceutiche, Università degli Studi di Firenze, Via Ugo Schiff 6, Sesto Fiorentino (Firenze), I-50019, Italy.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D000840:Anisoles / Q000138:chemical synthesis / Q000737:chemistry*; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular
chemical_list: D000840:Anisoles; D002257:Carbonic Anhydrase Inhibitors; D007527:Isoenzymes; C005299:veratrole
keywords: Aldol condensation; Friedel-Crafts reaction; bromination; carbonic anhydrase; cyclopentenyl; enzyme inhibition