54130-89-1Relevant articles and documents
Design and Synthesis of Structure-Simplified Derivatives of Gonytolide for the Promotion of Innate Immune Responses
Kikuchi, Haruhisa,Hoshikawa, Tsuyoshi,Kurata, Shoichiro,Katou, Yasuhiro,Oshima, Yoshiteru
, p. 1259 - 1266 (2016/06/09)
Gonytolide A (1), a dimeric chromanone substituted with the-lactone, shows promoting activity of innate immune responses. However, biological studies on this compound have been limited by the low amounts of 1 available from natural resources and the difficulty of its synthesis. In this study, we designed and synthesized structure-simplified gonytolide derivatives. Bischromone 10 and biflavone 13 both promoted the mammalian TNF-α signaling pathway and Drosophila innate immunity. They did not contain a chiral center and were easy to synthesize. Hence, they can be used as lead compounds for a new type of immunostimulating drugs and as research reagents.
Regioselective Reductive Electrophilic Substitution of 1,2,3-Trimethoxybenzene and Its 5-Alkyl-Substituted Homologues
Azzena, Ugo,Denurra, Teresa,Melloni, Giovanni,Piroddi, Anna Maria
, p. 5386 - 5390 (2007/10/02)
The methoxy group in the 2-position of 1,2,3-trimethoxybenzene (1) can be regioselectively removed by electron transfer from alkali metals and replaced with a variety of electrophiles in a one-pot procedure, affording 2-substituted resorcinol dimethyl ethers.The usefulness of this synthetic method is illustrated by numerous examples.This reaction procedure has been successfully extended to the 5-methyl-substituted homologue (2), but limitations occur with the higher homologue 1-pentyl-3,4,5-trimethoxybenzene (3).Investigations on the mechanism of demethoxylation, with the aid of labeling experiments, provided clear evidence for the intermediacy of aryl radicals and explained the low yields obtained in the reductive electrophilic substitution of compound 3.