Enantiopure sulforaphane analogues with various substituents at the sulfinyl sulfur: asymmetric synthesis and biological activities.
A convergent and high-yielding approach for the asymmetric synthesis of sulforaphane 2 and four analogues differently substituted at the sulfinyl sulfur has been developed. The key step of the synthesis is the diastereoselective synthesis of sulfinate ester 23-S(S), using the DAG (diacetone-D-glucofuranose)-methodology. The biological activity of these compounds as inductors of phase II detoxifying enzyme has been studied by determining their ability to activate the cytoprotective transcription factor Nrf2.
Khiar
Noureddine
N
Instituto de Investigaciones Químicas, C.S.I.C-Universidad de Sevilla, c/. Américo Vespucio, 49., Isla de la Cartuja, 41092 Sevilla, Spain. khiar@iiq.csic.es
Werner
Sabine
S
Mallouk
Siham
S
Lieder
Franziska
F
Alcudia
Ana
A
Fernández
Inmaculada
I
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000378:metabolism; D002460:Cell Line; D019610:Cytoprotection / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004790:Enzyme Induction / Q000187:drug effects; D006801:Humans; D017879:Isothiocyanates; D050217:Metabolic Detoxication, Phase II; D051267:NF-E2-Related Factor 2 / Q000378:metabolism; D051381:Rats; D020218:Response Elements / Q000235:genetics; D013237:Stereoisomerism; D013454:Sulfoxides; D013455:Sulfur / Q000737:chemistry*; D013861:Thiocyanates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D000975:Antioxidants; D017879:Isothiocyanates; D051267:NF-E2-Related Factor 2; D013454:Sulfoxides; D013861:Thiocyanates; D013455:Sulfur; C016766:sulforaphane