Synthesis, cytotoxicities, and carbonic anhydrase inhibition potential of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

被引：26

作者：

Bilginer, Sinan ^{[1
]}

Gul, Halise Inci ^{[1
]}

Erdal, Feyza Sena ^{[1
]}

Sakagami, Hiroshi ^{[2
]}

Levent, Serkan ^{[3
]}

Gulcin, Ilhami ^{[4
]}

Supuran, Claudiu T. ^{[5
]}

机构：

[1] Ataturk Univ, Fac Pharm, Dept Pharmaceut Chem, TR-25240 Erzurum, Turkey

[2] Meikai Univ, Meikai Univ Res Inst Odontol M RIO, Sch Dent, Sakado, Saitama, Japan

[3] Anadolu Univ, Fac Pharm, Dept Pharmaceut Chem, Eskisehir, Turkey

[4] Ataturk Univ, Fac Sci, Dept Chem, Erzurum, Turkey

[5] Univ Firenze, Neurofarba Dept, Florence, Italy

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2019年 / 34卷 / 01期

关键词：

Anticancer; benzoxazolone; carbonic anhydrase; chalcone; cytotoxic; MANNICH-BASES; ANTICANCER; DERIVATIVES; CHALCONES; APOPTOSIS; ACETYLCHOLINESTERASE; BIOACTIVITY; LICORICE; ACID;

D O I：

10.1080/14756366.2019.1670657

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In this study, new chalcone compounds having the chemical structure of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones (1?8) were synthesised and were characterised by H-1-NMR, C-13?-NMR, and HRMS spectra. Cytotoxic and carbonic anhydrase (CA) inhibitory effects of the compounds were investigated. Cytotoxicity results pointed out that compound 4, 6-[3-(4-trifluoromethylphenyl)-2-propenoyl]-3H-benzoxazol-2-one, showed the highest cytotoxicity (CC50) and potency-selectivity expression (PSE) value, and thus can be considered as a lead compound of this study. According to the CA inhibitory results, IC50 values of the compounds 1?8 towards hCA I were in the range of 29.74?69.57??M, while they were in the range of 18.14 ? 48.46??M towards hCA II isoenzyme. K-i values of the compounds 1?8 towards hCA I were in the range of 28.37???6.63?70.58???6.67??M towards hCA I isoenzyme and they were in the range of 10.85???2.14 ? 37.96???2.36??M towards hCA II isoenzyme.

引用

页码：1722 / 1729

页数：8

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