Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological Activities
Eleven conjugates between dihydroartemisinin (DHA) with thiols containing both ether and thioether bonds were designed, synthesized by a two-step procedure including etherification and S-alkylation. Analysis of the NMR spectral data indicated that the dimer of DHA with thiols 6-mercaptopurine and 2-...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2023-01-01
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| Series: | Heteroatom Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2023/6761186 |
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| author | Ngoc Hung Truong Thi Hong Ha Tran Kim Chi Hoang Duc Bao Ninh Viet Duc Le Duc Anh Le Van Chinh Luu |
| author_facet | Ngoc Hung Truong Thi Hong Ha Tran Kim Chi Hoang Duc Bao Ninh Viet Duc Le Duc Anh Le Van Chinh Luu |
| author_sort | Ngoc Hung Truong |
| collection | DOAJ |
| description | Eleven conjugates between dihydroartemisinin (DHA) with thiols containing both ether and thioether bonds were designed, synthesized by a two-step procedure including etherification and S-alkylation. Analysis of the NMR spectral data indicated that the dimer of DHA with thiols 6-mercaptopurine and 2-mercaptoimidazole was produced with yields of 31% and 62%, respectively. Furthermore, the tautomerization of thiol 5-methoxy-2-mercaptobenzimidazole led to the formation of a mixture of two isomers in which they might be interchangeable through a dynamic tautomeric equilibrium in the solution. Screening in vitro biological activities revealed that most of the synthesized conjugates showed good cytotoxic and anti-inflammatory activity, while three of them displayed α-glucosidase inhibitory activity. Notably, two conjugates 5d and 5e of DHA with thiols 2-mercaptopyrimidine and 2-mercaptobenzothiazole had an effect in all tested activities in which conjugate 5e is the most potent. |
| format | Article |
| id | doaj-art-40bdba517df74a189cbdf55a561bd897 |
| institution | Kabale University |
| issn | 1098-1071 |
| language | English |
| publishDate | 2023-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Heteroatom Chemistry |
| spelling | doaj-art-40bdba517df74a189cbdf55a561bd8972025-02-03T06:04:51ZengWileyHeteroatom Chemistry1098-10712023-01-01202310.1155/2023/6761186Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological ActivitiesNgoc Hung Truong0Thi Hong Ha Tran1Kim Chi Hoang2Duc Bao Ninh3Viet Duc Le4Duc Anh Le5Van Chinh Luu6Institute of Natural Products ChemistryInstitute of Natural Products ChemistryInstitute of Natural Products ChemistryTruman State UniversitySchool of Chemical EngineeringInstitute of Chemistry and MaterialInstitute of Natural Products ChemistryEleven conjugates between dihydroartemisinin (DHA) with thiols containing both ether and thioether bonds were designed, synthesized by a two-step procedure including etherification and S-alkylation. Analysis of the NMR spectral data indicated that the dimer of DHA with thiols 6-mercaptopurine and 2-mercaptoimidazole was produced with yields of 31% and 62%, respectively. Furthermore, the tautomerization of thiol 5-methoxy-2-mercaptobenzimidazole led to the formation of a mixture of two isomers in which they might be interchangeable through a dynamic tautomeric equilibrium in the solution. Screening in vitro biological activities revealed that most of the synthesized conjugates showed good cytotoxic and anti-inflammatory activity, while three of them displayed α-glucosidase inhibitory activity. Notably, two conjugates 5d and 5e of DHA with thiols 2-mercaptopyrimidine and 2-mercaptobenzothiazole had an effect in all tested activities in which conjugate 5e is the most potent.http://dx.doi.org/10.1155/2023/6761186 |
| spellingShingle | Ngoc Hung Truong Thi Hong Ha Tran Kim Chi Hoang Duc Bao Ninh Viet Duc Le Duc Anh Le Van Chinh Luu Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological Activities Heteroatom Chemistry |
| title | Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological Activities |
| title_full | Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological Activities |
| title_fullStr | Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological Activities |
| title_full_unstemmed | Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological Activities |
| title_short | Novel Thioethers of Dihydroartemisinin Exhibiting Their Biological Activities |
| title_sort | novel thioethers of dihydroartemisinin exhibiting their biological activities |
| url | http://dx.doi.org/10.1155/2023/6761186 |
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