Carbohydrate-based furopyran-3-ones: synthesis via a rare carbonyl nucleophilic 1,2-migration induced by TMSOTf and antifungal activity

Autor:	Wei-Wei Han, Shang-Shang Qin, Yu Hou, Hong-Min Liu, Xiu-Fang Shi, Liu Fengwu, Shi-Qing Zhu, Fu-Qiang Wang, Hui-Ying Song, Yong-Kang Jia, Shi-Yao Meng, Ming Li
Rok vydání:	2015
Předmět:	biology Trimethylsilyl Stereochemistry Epidermophyton floccosum Organic Chemistry Trichophyton rubrum biology.organism_classification Candida parapsilosis Biochemistry chemistry.chemical_compound chemistry Nucleophile Drug Discovery Microsporum canis Candida albicans Trifluoromethanesulfonate
Zdroj:	Tetrahedron. 71:9420-9428
ISSN:	0040-4020
DOI:	10.1016/j.tet.2015.10.054
Popis:	A versatile method for synthesis of chiral furopyran-β-one analogues starting from 1,4:3,6-dianhydrofructose has been developed. The target compounds were acquired by treatment of 1,4:3,6-dianhydrofructose with benzaldehydes in the presence of KF/Al2O3 and subsequent ring expansion of furanones induced by TMSOTf (trimethylsilyl triflate). The ring expansion involves an unprecedented nucleophilic 1,2-migration of a keto-carbonyl as a key step. In vitro antifungal activity of all compounds obtained were evaluated against five human pathogenic fungi (Candida parapsilosis ATCC22019, Candida albicans ATCC10231, Trichophyton rubrum CMCC(F)T1f, Epidermophyton floccosum CMCC(F)E1d, and Microsporum canis CMCC(F)M3d). We found that the furopyran-β-one analogues bearing chloro or fluoro group showed significant inhibitory activity against dermatophytes, especially M. canis.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d57bfdc9b35238f5932c2acfe10881f7 https://doi.org/10.1016/j.tet.2015.10.054 Zobrazit plný text záznamu Full Text from ScienceDirect