Synthesis and evaluation of new benzodioxole-based dithiocarbamate derivatives as potential anticancer agents and hCA-I and hCA-II inhibitors
| Autor: | Ahmet Özdemir, Belgin Sever, Mehlika Dilek Altıntop, Seyedeh Sara Soleimani, Hayrunnisa Nadaroglu, Kaan Kucukoglu, Gülşen Akalın Çiftçi, Zafer Asım Kaplancıklı |
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| Přispěvatelé: | Anadolu Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, Altıntop, Mehlika Dilek, Sever, Belgin, Çiftçi, Gülsen Akalın, Özdemir, Ahmet, Kaplancıklı, Zafer Asım |
| Rok vydání: | 2016 |
| Předmět: |
Carbonic Anhydrase I
Stereochemistry Cell Survival Antineoplastic Agents 01 natural sciences Medicinal chemistry Carbonic Anhydrase II chemistry.chemical_compound Structure-Activity Relationship Thiocarbamates Cell Line Tumor Drug Discovery Ic50 values medicine Cytotoxic T cell Animals Humans Benzodioxoles Dithiocarbamate Carbonic Anhydrase Inhibitors Inhibitory effect IC50 Cancer Pharmacology chemistry.chemical_classification Cisplatin Dose-Response Relationship Drug 010405 organic chemistry Chemistry Organic Chemistry General Medicine Human Carbonic Anhydrase 0104 chemical sciences Sodium salt Rats 010404 medicinal & biomolecular chemistry Benzodioxole Acetamide medicine.drug |
| Zdroj: | European journal of medicinal chemistry. 125 |
| ISSN: | 1768-3254 |
| Popis: | WOS: 000390496600012 PubMed ID: 27657811 In the current work, new benzodioxole-based dithiocarbamate derivatives were synthesized via the reaction of N-(1,3-benzodioxol-5-ylmethyl)-2-chloroacetamide with appropriate sodium salts of N,N-disubstituted dithiocarbamic acids. These derivatives were evaluated for their cytotoxic effects on A549 human lung adenocarcinoma and C6 rat glioma cell lines. N-(1,3-Benzodioxol-5-ylmethyl)-2-[4-(4-nitrophenyl)-1-piperazinylthiocarbamoylthio]acetamide (10) can be identified as the most promising anticancer agent against C6 cell line due to its notable inhibitory effect on C6 cells with an IC50 value of 23.33 +/- 7.63 mu g/mL when compared with cisplatin (IC50 = 19.00 +/- 5.29 mu g/mL). On the other hand, compound 10 did not show any significant cytotoxic activity against A549 cell line. The compounds were also tested for their in vitro inhibitory effects on hCA-I and hCA-II. Generally, the tested compounds were more effective on CAs than acetazolamide, the reference agent. Among these compounds, N-(1,3-benzodioxol-5-ylmethyl)-2-[(morpholinyl)thiocarbamoylthio]acetamide (3) and N-(1,3-benzodioxol-5-ylmethyl)-2-[(thiomorpholinyl)thiocarbamoylthio]acetamide (4) were found to be the most effective compounds on hCA-I with IC50 values of 0.346 nM and 0.288 nM, and hCA-II with IC50 values of 0.287 nM and 0338 nM, respectively Anadolu University Scientific Research Projects Commission [1404S123] This study was supported by Anadolu University Scientific Research Projects Commission under the grant no: 1404S123. |
| Databáze: | OpenAIRE |
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