62872-62-2Relevant academic research and scientific papers
A new approach for the total synthesis of spilanthol and analogue with improved anesthetic activity
Alonso, Isabella G.,Yamane, Lais T.,de Freitas-Blanco, Ver?nica S.,Novaes, Luiz F.T.,Franz-Montan, Michelle,de Paula, Eneida,Rodrigues, Marili V.N.,Rodrigues, Rodney A.F.,Pastre, Julio C.
supporting information, p. 5192 - 5199 (2018/07/06)
A 5-step synthesis of spilanthol (affinin) is reported, where the route features complete control of alkene geometry during the assembling of the double bonds, with the use of a Sonogashira cross-coupling reaction, a Z-selective alkyne semi-reduction and a HWE olefination reaction as the key steps. A simplified analogue was also prepared in 4 steps. Both compounds were found to permeate dermatomed pig ear skin through an in vitro Franz-type diffusion cell. The simplified analogue presented a superior anesthetic effect in vivo, using the tail flick model, when compared to spilanthol and to the commercial standard EMLA. These results suggest that both spilanthol and its analogue could be useful as a topical anesthetic in clinical practice.
METHOD FOR PRODUCING SANSHOOL
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Paragraph 0084; 0085; 0086, (2013/09/26)
Provided are a method for producing a sanshool, which method has a short process and exhibits high stereoselectivity, as well as an iron carbonyl complex compound that is an intermediate useful for the production method. A diene iron complex compound characterized by being represented by the following general formula (I): (in which A represents CO, P(RA)3, CN, NO, SO(RA)3, or N(RA)2; RA represents a straight chain or branched chain alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms; and one of R1 and R2 represents a hydrogen atom and the other one thereof represents a structure represented by the following formula (II)): (in which R represents a hydrogen atom, a hydroxyl group, or a methyl group).
