Discovery of tetrazole thioethers: An efficient, environmentally friendly and metal-free S-arylation using diaryliodonium salts
An efficient, environmentally friendly, and metal-free method for the synthesis of functionalized tetrazole thioethers via the S-arylation of tetrazole-5-thiones using diaryliodonium salts as aryl transfer reagents has been developed. This novel methodology provides rapid access to tetrazole thioeth...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-11-01
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| Series: | Journal of Saudi Chemical Society |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610324001388 |
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| author | Xiaogang Li Xuesong Wang Yan Wang Yinfeng Tan Dong Liu Xueying Zhang Youbin Li Junyu Xu |
| author_facet | Xiaogang Li Xuesong Wang Yan Wang Yinfeng Tan Dong Liu Xueying Zhang Youbin Li Junyu Xu |
| author_sort | Xiaogang Li |
| collection | DOAJ |
| description | An efficient, environmentally friendly, and metal-free method for the synthesis of functionalized tetrazole thioethers via the S-arylation of tetrazole-5-thiones using diaryliodonium salts as aryl transfer reagents has been developed. This novel methodology provides rapid access to tetrazole thioether derivatives under facile conditions. Our study underscores the chemoselectivity of unsymmetrical diaryliodonium salts, emphasizing their preference for the transfer of sterically hindered and electron-deficient aryl groups. Notably, the synthesized compound 3h exhibits antitumor activity against A2780 (ovarian cancer) and MDA-MB-231 (breast cancer) tumor cells. In silico studies predict these compounds to possess good drug-likeness and low toxicity risk. These findings highlight the potential of functionalized tetrazole thioethers as antiproliferative agents and pave the way for further development and optimization in future investigations. |
| format | Article |
| id | doaj-art-37c81918ee3148999762c01b101109af |
| institution | Kabale University |
| issn | 1319-6103 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj-art-37c81918ee3148999762c01b101109af2024-12-19T10:52:38ZengElsevierJournal of Saudi Chemical Society1319-61032024-11-01286101943Discovery of tetrazole thioethers: An efficient, environmentally friendly and metal-free S-arylation using diaryliodonium saltsXiaogang Li0Xuesong Wang1Yan Wang2Yinfeng Tan3Dong Liu4Xueying Zhang5Youbin Li6Junyu Xu7Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, ChinaEngineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, ChinaEngineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, ChinaEngineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, ChinaEngineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, ChinaEngineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, ChinaEngineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, China; Corresponding author.Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, China; International Joint Research Center of Human-machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Haikou Key Laboratory of Li Nationality Medicine, Hainan Academy of Medical Sciences, Haikou 571199, China; Corresponding author at: Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, Hainan Provincial Key Laboratory of R&D on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, China.An efficient, environmentally friendly, and metal-free method for the synthesis of functionalized tetrazole thioethers via the S-arylation of tetrazole-5-thiones using diaryliodonium salts as aryl transfer reagents has been developed. This novel methodology provides rapid access to tetrazole thioether derivatives under facile conditions. Our study underscores the chemoselectivity of unsymmetrical diaryliodonium salts, emphasizing their preference for the transfer of sterically hindered and electron-deficient aryl groups. Notably, the synthesized compound 3h exhibits antitumor activity against A2780 (ovarian cancer) and MDA-MB-231 (breast cancer) tumor cells. In silico studies predict these compounds to possess good drug-likeness and low toxicity risk. These findings highlight the potential of functionalized tetrazole thioethers as antiproliferative agents and pave the way for further development and optimization in future investigations.http://www.sciencedirect.com/science/article/pii/S1319610324001388Tetrazole thioetherDiaryliodonium saltsMetal-free cross-couplingSelective arylationAntitumor |
| spellingShingle | Xiaogang Li Xuesong Wang Yan Wang Yinfeng Tan Dong Liu Xueying Zhang Youbin Li Junyu Xu Discovery of tetrazole thioethers: An efficient, environmentally friendly and metal-free S-arylation using diaryliodonium salts Journal of Saudi Chemical Society Tetrazole thioether Diaryliodonium salts Metal-free cross-coupling Selective arylation Antitumor |
| title | Discovery of tetrazole thioethers: An efficient, environmentally friendly and metal-free S-arylation using diaryliodonium salts |
| title_full | Discovery of tetrazole thioethers: An efficient, environmentally friendly and metal-free S-arylation using diaryliodonium salts |
| title_fullStr | Discovery of tetrazole thioethers: An efficient, environmentally friendly and metal-free S-arylation using diaryliodonium salts |
| title_full_unstemmed | Discovery of tetrazole thioethers: An efficient, environmentally friendly and metal-free S-arylation using diaryliodonium salts |
| title_short | Discovery of tetrazole thioethers: An efficient, environmentally friendly and metal-free S-arylation using diaryliodonium salts |
| title_sort | discovery of tetrazole thioethers an efficient environmentally friendly and metal free s arylation using diaryliodonium salts |
| topic | Tetrazole thioether Diaryliodonium salts Metal-free cross-coupling Selective arylation Antitumor |
| url | http://www.sciencedirect.com/science/article/pii/S1319610324001388 |
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