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

• Published in: Bioorganic chemistry Vol. 70; pp. 118 - 125
• Main Authors: Kocyigit, Umit M., Budak, Yakup, Gürdere, Meliha Burcu, Tekin, Şaban, Köprülü, Tuğba Kul, Ertürk, Fatih, Özcan, Kezban, Gülçin, İlhami, Ceylan, Mustafa
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.02.2017; Elsevier
• Subjects: Animals; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Anticancer; Antimicrobial; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Bacteria - drug effects; Bacterial Infections - drug therapy; Biochemistry & Molecular Biology; Carbonic anhydrase; Carbonic Anhydrase I - antagonists & inhibitors; Carbonic Anhydrase II - antagonists & inhibitors; Carbonic Anhydrase Inhibitors - chemical synthesis; Carbonic Anhydrase Inhibitors - chemistry; Carbonic Anhydrase Inhibitors - pharmacology; Cell Line, Tumor; Chalcone; Chalcone - chemical synthesis; Chalcone - chemistry; Chalcone - pharmacology; Chemistry; Chemistry, Organic; Fungi - drug effects; Humans; Isoindole; Isoindoles - chemical synthesis; Isoindoles - chemistry; Isoindoles - pharmacology; Life Sciences & Biomedicine; Mycoses - drug therapy; Neoplasms - drug therapy; Physical Sciences; Rats; Science & Technology; Structure-Activity Relationship; Antimicrobial; C6; Carbonic anhydrase; Anticancer; Isoindole; Chalcone; BUTYRYLCHOLINESTERASE; ISOENZYMES I; LACTOPEROXIDASE; DISCOVERY; SULFAMIDES; POTENT; CHALCONE DERIVATIVES; ACETYLCHOLINE ESTERASE; ANTIOXIDANT; GLUTATHIONE-S-TRANSFERASE
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2016.12.001

[Display omitted] •Synthesis of new hybrid compounds containing chalcone and methanoisoindole units.•Anticancer and antimicrobial activities of newly synthesized compounds were evaluation.•Inhibition effects of newly synthesized compounds against hCA I, and II were determined.•IC50 values of the most effective compounds against hCA I, and II are 466.35 and 352.49pM, respectively. 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.