Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors
A new series of phthalazine substituted urea and thiourea derivatives were synthesized, and their inhibitory effects on the activity of purified human carbonic anhydrases (hCAs I and II) were evaluated. 2H-Indazolo[2,1-b]phthalazine-trione derivative (1) was prepared with 4-nitrobenzaldehyde, dimedo...
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| Format: | Article |
| Language: | English |
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Wiley
2013-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2013/742178 |
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| author | Nurcan Berber Mustafa Arslan Emre Yavuz Cigdem Bilen Nahit Gencer |
| author_facet | Nurcan Berber Mustafa Arslan Emre Yavuz Cigdem Bilen Nahit Gencer |
| author_sort | Nurcan Berber |
| collection | DOAJ |
| description | A new series of phthalazine substituted urea and thiourea derivatives were synthesized, and their inhibitory effects on the activity of purified human carbonic anhydrases (hCAs I and II) were evaluated. 2H-Indazolo[2,1-b]phthalazine-trione derivative (1) was prepared with 4-nitrobenzaldehyde, dimedone, and phthalhydrazide in the presence of TFA in DMF, and nitro group was reduced to amine derivative (2) with SnCl2·2H2O. The compound was reacted with isocyanates and isothiocyanates to get the final products (3a–p). The results showed that all the synthesized compounds inhibited the CA isoenzymes activity. 3a (IC50 = 6.40 µM for hCA I and 6.13 µM for hCA II) has the most inhibitory effect. The synthesized compounds are very bulky to be able to bind near the zinc ion, and they much more probably bind as the coumarin derivatives. |
| format | Article |
| id | doaj-art-8309390ea6784a6a9e95a3f357f2b031 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-8309390ea6784a6a9e95a3f357f2b0312025-02-03T01:11:45ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/742178742178Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase InhibitorsNurcan Berber0Mustafa Arslan1Emre Yavuz2Cigdem Bilen3Nahit Gencer4Department of Chemistry, Faculty of Art and Sciences, Sakarya University, 54147 Sakarya, TurkeyDepartment of Chemistry, Faculty of Art and Sciences, Sakarya University, 54147 Sakarya, TurkeyDepartment of Chemistry, Faculty of Art and Sciences, Balikesir University, 10145 Balikesir, TurkeyDepartment of Chemistry, Faculty of Art and Sciences, Balikesir University, 10145 Balikesir, TurkeyDepartment of Chemistry, Faculty of Art and Sciences, Balikesir University, 10145 Balikesir, TurkeyA new series of phthalazine substituted urea and thiourea derivatives were synthesized, and their inhibitory effects on the activity of purified human carbonic anhydrases (hCAs I and II) were evaluated. 2H-Indazolo[2,1-b]phthalazine-trione derivative (1) was prepared with 4-nitrobenzaldehyde, dimedone, and phthalhydrazide in the presence of TFA in DMF, and nitro group was reduced to amine derivative (2) with SnCl2·2H2O. The compound was reacted with isocyanates and isothiocyanates to get the final products (3a–p). The results showed that all the synthesized compounds inhibited the CA isoenzymes activity. 3a (IC50 = 6.40 µM for hCA I and 6.13 µM for hCA II) has the most inhibitory effect. The synthesized compounds are very bulky to be able to bind near the zinc ion, and they much more probably bind as the coumarin derivatives.http://dx.doi.org/10.1155/2013/742178 |
| spellingShingle | Nurcan Berber Mustafa Arslan Emre Yavuz Cigdem Bilen Nahit Gencer Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors Journal of Chemistry |
| title | Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors |
| title_full | Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors |
| title_fullStr | Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors |
| title_full_unstemmed | Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors |
| title_short | Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors |
| title_sort | synthesis and evaluation of new phthalazine urea and thiourea derivatives as carbonic anhydrase inhibitors |
| url | http://dx.doi.org/10.1155/2013/742178 |
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