Arylsulfonamido-alkyl-sulfamates act as inhibitors of bovine carbonic anhydrase II
A small library of arylsulfonamido-alkyl sulfamates was prepared by a two-step synthesis from readily available starting materials. The compounds were tested for their ability to inhibit bovine carbonic anhydrase II. Several of them were found as good competitive inhibitors holding Ki values as low...
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Elsevier
2024-12-01
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| Series: | European Journal of Medicinal Chemistry Reports |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772417424000499 |
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| author | Toni C. Denner Niels V. Heise René Csuk |
| author_facet | Toni C. Denner Niels V. Heise René Csuk |
| author_sort | Toni C. Denner |
| collection | DOAJ |
| description | A small library of arylsulfonamido-alkyl sulfamates was prepared by a two-step synthesis from readily available starting materials. The compounds were tested for their ability to inhibit bovine carbonic anhydrase II. Several of them were found as good competitive inhibitors holding Ki values as low as Ki = 0.9 μM (compound 47b). The activity was influenced by the substitution pattern of the arylsulfonamide moiety as well as the length of the spacer to the distal sulfamate group. Molecular docking studies were used to substantiate these findings. For the aryl-substituted analogues, the increase in inhibitory activity for compounds with a shorter spacer can be explained by stabilization via aromatic π-interactions. For the cyclopropyl or methylsulfonyl substituted analogues, their inhibitory activity can be attributed to their reduced steric hindrance. These results provide a basis for designing effective CA II inhibitors. |
| format | Article |
| id | doaj-art-afb6e6bcd7b241d89be30adab3d497ad |
| institution | Kabale University |
| issn | 2772-4174 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | European Journal of Medicinal Chemistry Reports |
| spelling | doaj-art-afb6e6bcd7b241d89be30adab3d497ad2024-12-05T05:21:46ZengElsevierEuropean Journal of Medicinal Chemistry Reports2772-41742024-12-0112100177Arylsulfonamido-alkyl-sulfamates act as inhibitors of bovine carbonic anhydrase IIToni C. Denner0Niels V. Heise1René Csuk2Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), GermanyOrganic Chemistry, Martin-Luther-University Halle-Wittenberg, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), GermanyCorresponding author.; Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), GermanyA small library of arylsulfonamido-alkyl sulfamates was prepared by a two-step synthesis from readily available starting materials. The compounds were tested for their ability to inhibit bovine carbonic anhydrase II. Several of them were found as good competitive inhibitors holding Ki values as low as Ki = 0.9 μM (compound 47b). The activity was influenced by the substitution pattern of the arylsulfonamide moiety as well as the length of the spacer to the distal sulfamate group. Molecular docking studies were used to substantiate these findings. For the aryl-substituted analogues, the increase in inhibitory activity for compounds with a shorter spacer can be explained by stabilization via aromatic π-interactions. For the cyclopropyl or methylsulfonyl substituted analogues, their inhibitory activity can be attributed to their reduced steric hindrance. These results provide a basis for designing effective CA II inhibitors.http://www.sciencedirect.com/science/article/pii/S2772417424000499SulfamatesCarbonic anhydrase IIInhibitor |
| spellingShingle | Toni C. Denner Niels V. Heise René Csuk Arylsulfonamido-alkyl-sulfamates act as inhibitors of bovine carbonic anhydrase II European Journal of Medicinal Chemistry Reports Sulfamates Carbonic anhydrase II Inhibitor |
| title | Arylsulfonamido-alkyl-sulfamates act as inhibitors of bovine carbonic anhydrase II |
| title_full | Arylsulfonamido-alkyl-sulfamates act as inhibitors of bovine carbonic anhydrase II |
| title_fullStr | Arylsulfonamido-alkyl-sulfamates act as inhibitors of bovine carbonic anhydrase II |
| title_full_unstemmed | Arylsulfonamido-alkyl-sulfamates act as inhibitors of bovine carbonic anhydrase II |
| title_short | Arylsulfonamido-alkyl-sulfamates act as inhibitors of bovine carbonic anhydrase II |
| title_sort | arylsulfonamido alkyl sulfamates act as inhibitors of bovine carbonic anhydrase ii |
| topic | Sulfamates Carbonic anhydrase II Inhibitor |
| url | http://www.sciencedirect.com/science/article/pii/S2772417424000499 |
| work_keys_str_mv | AT tonicdenner arylsulfonamidoalkylsulfamatesactasinhibitorsofbovinecarbonicanhydraseii AT nielsvheise arylsulfonamidoalkylsulfamatesactasinhibitorsofbovinecarbonicanhydraseii AT renecsuk arylsulfonamidoalkylsulfamatesactasinhibitorsofbovinecarbonicanhydraseii |