The first synthesis of the indole phytoalexin cyclobrassinon and some of its analogues, possessing a thiazino[6,5-b]indol-4-onetricyclic ring system was performed starting from 1-substitued 2-chloroindole-3-carboxaldehydes. The route employed the intramolecular Et3N-mediated or photochemical nucleophilic substitution of a chlorine atom in the 2-position of the indole ring with a sulfur atom as a key step. Examination of biological activity against the selected tumor cell lines, bacteria and fungi revealed no expressive activity of synthesized compounds.
A new approach to the synthesis of rare thiazino[6,5-b]indol-4-one derivatives. First total synthesis of the indole phytoalexins cyclobrassinon / P., Kutchy; M., Suchy; A., Andreani; M., Dzurilla; V., Kovacik; J., Alfoldi; Rossi, Maddalena; M., Gramatova. - In: TETRAHEDRON. - ISSN 0040-4020. - ELETTRONICO. - 58:44(2002), pp. 9029-9039. [10.1016/S0040-4020(02)01124-9]
A new approach to the synthesis of rare thiazino[6,5-b]indol-4-one derivatives. First total synthesis of the indole phytoalexins cyclobrassinon.
ROSSI, Maddalena;
2002
Abstract
The first synthesis of the indole phytoalexin cyclobrassinon and some of its analogues, possessing a thiazino[6,5-b]indol-4-onetricyclic ring system was performed starting from 1-substitued 2-chloroindole-3-carboxaldehydes. The route employed the intramolecular Et3N-mediated or photochemical nucleophilic substitution of a chlorine atom in the 2-position of the indole ring with a sulfur atom as a key step. Examination of biological activity against the selected tumor cell lines, bacteria and fungi revealed no expressive activity of synthesized compounds.
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