Synthesis of 4-(2-substituted hydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects

被引:63
作者
Gul, Halise Inci [1 ]
Kucukoglu, Kaan [1 ]
Yamali, Cem [1 ]
Bilginer, Sinan [1 ]
Yuca, Hafize [2 ]
Ozturk, Iknur [2 ]
Taslimi, Parham [3 ]
Gulcin, Ilhami [3 ,4 ]
Supuran, Claudiu T. [5 ]
机构
[1] Ataturk Univ, Fac Pharm, Dept Pharmaceut Chem, Erzurum, Turkey
[2] Ataturk Univ, Fac Pharm, Erzurum, Turkey
[3] Ataturk Univ, Fac Sci, Dept Chem, Erzurum, Turkey
[4] King Saud Univ, Coll Sci, Dept Zool, Riyadh, Saudi Arabia
[5] Univ Florence, Chim Bioorgan Lab, Polo Sci, Florence, Italy
关键词
2-Acethylfuran; 2-acethylthiophene; acetophenones; carbonic anhydrase; enzyme inhibition; indanone; sulfonamide; TROUT ONCORHYNCHUS-MYKISS; ERYTHROCYTES IN-VITRO; THERAPEUTIC APPLICATIONS; SULFONAMIDE DERIVATIVES; ENZYME-ACTIVITY; ISOENZYMES I; ISOZYMES I; ISOFORMS I; PURIFICATION; PEROXIDASE;
D O I
10.3109/14756366.2015.1047359
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, 4-(2-substituted hydrazinyl)benzenesulfonamides were synthesized by microwave irradiation and their chemical structures were confirmed by H-1 NMR, (CNMR)-C-13, and HRMS. Ketones used were: Acetophenone (S1), 4-methylacetophenone (S2), 4-chloroacetophenone (S3), 4-fluoroacetophenone (S4), 4-bromoacetophenone (S5), 4-methoxyacetophenone (S6), 4-nitroacetophenone (S7), 2-acetylthiophene (S8), 2-acetylfuran (S9), 1-indanone (S10), 2-indanone (S11). The compounds S9, S10 and S11 were reported for the first time, while S1-S8 was synthesized by different method than literature reported using microwave irradiation method instead of conventional heating in this study. The inhibitory effects of 4-(2-substituted hydrazinyl) benzenesulfonamide derivatives (S1-S11) against hCA I and II were studied. Cytosolic hCA I and II isoenzymes were potently inhibited by new synthesized sulphonamide derivatives with K-is in the range of 1.79 +/- 0.22-2.73 +/- 0.08 nM against hCA I and in the range of 1.72 +/- 0.58-11.64 +/- 5.21nM against hCA II, respectively.
引用
收藏
页码:568 / 573
页数:6
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