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Synthesis, cytotoxic, and carbonic anhydrase inhibitory effects of new 2‐(3‐(4‐methoxyphenyl)‐5‐(aryl)‐4,5 ‐dihydro‐1 H ‐pyrazol‐1‐yl)benzo[ d ]thiazole derivatives
Author(s) -
Tugrak Mehtap,
Gul Halise Inci,
Sakagami Hiroshi,
Gulcin Ilhami
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3985
Subject(s) - chemistry , thiazole , stereochemistry , carbonic anhydrase , carbonic anhydrase ii , aryl , cytotoxicity , potency , enzyme , carbonic anhydrase i , selectivity , ic50 , thiophene , mtt assay , in vitro , biochemistry , organic chemistry , alkyl , catalysis
2‐(3‐[4‐Methoxyphenyl]‐5‐aryl‐4,5‐dihydro‐1 H ‐pyrazol‐1‐yl)benzo[ d ]thiazoles ( 1b‐7b ) were synthesized for the first time except 1b , and spectral methods such as 1 H NMR, 13 C NMR and HRMS were utilized to illuminate the chemical structures of the synthesized compounds. Phenyl ( 1b ), 2‐methoxyphenyl ( 2b ), 4‐methoxyphenyl ( 3b ), 4‐methoxy‐3‐hydroxyphenyl ( 4b ), 2,5‐dimethoxyphenyl ( 5b ), 3,4,5‐trimethoxyphenyl ( 6b ), or thiophene‐2‐yl ( 7b ) was used as a aryl part. The inhibitory effects of the compounds were evaluated toward human carbonic anhydrase I and II enzymes (hCA I and hCA II). In vitro cytotoxic effects of the compounds against human oral squamous carcinomas and human normal oral cells were carried out via MTT. The compounds ( 1b‐7b ) had Ki values of 36.87 ± 11.62‐66.24 ± 2.99 μM (hCA I) and 22.66 ± 1.41‐89.95 ± 6.25 μM (hCA II). Compounds 1b (Ki = 36.87 ± 11.62 μM) toward hCA I, 6b (Ki = 22.66 ± 1.41 μM) toward hCA II had significant enzyme inhibitory potency. Compound 6b had the highest tumor selectivity (TS = 29.3) and potency selectivity expression (PSE = 272.3) values. Therefore, compounds 1b and 6b with CAs inhibition effect and compound 6b with the cytotoxicity may be forwarded to further studies as potent compounds.