81476-94-0Relevant articles and documents
2-Prenylated m-dimethoxybenzenes as potent inhibitors of 15-lipo-oxygenase: inhibitory mechanism and SAR studies
Jabbari, Atena,Sadeghian, Hamid,Salimi, Alireza,Mousavian, Mina,Seyedi, Seyed M.,Bakavoli, Mehdi
, p. 460 - 469 (2016/10/19)
15-lipo-oxygenases are one of the iron-containing proteins capable of performing peroxidation of unsaturated fatty acids in animals and plants. The critical role of enzymes in the formation of inflammations, sensitivities, and some cancers has been demonstrated in mammals. The importance of enzymes has led to the development of mechanistic studies, product analysis, and synthesis of inhibitors. In this study, a series of allyl and prenyl dimethoxybenzenes were synthesized and their inhibitory potency against soybean 15-Lipo-oxygenase (L1; EC 1,13,11,12) was determined. Among the synthetic compounds, 2,6-dimethoxy-1-isopentenyl-4-methylbenzene, 2,6-dimethoxy-1-geranyl-4-methylbenzene, and 2,6-dimethoxy-1-farnesyl-4-methylbenzene showed the most potent inhibitory activity with IC50 values of 7.6, 5.3, and 0.52?μm, respectively. For some of the compounds, SAR studies showed acceptable relationship between inhibitory potency and enzyme–ligand interactions. Radical scavenging assessment results apart from the SAR studies indicate that electronic properties are the major factors for lipo-oxygenase inhibition potency of the mentioned compounds. Based on the theoretical studies, it was suggested that CH…O intramolecular hydrogen bond between ortho-methoxy oxygen and methine hydrogen atoms is one of the major factors in the stability of 2,6-dimethoxyallyl(or prenyl)benzenes radical via the planarity fixation between phenyl and allyl (or prenyl) pi orbitals.
Synthetic Studies of Fungal Metabolites: Ascofuranone and Colletochlorin D
Guthrie, Anne E.,Semple, Edward J.,Joullie, Madeleine M.
, p. 2369 - 2376 (2007/10/02)
Procedures have been developed for the synthesis of hexasubstituted aromatic rings which are present in many fungal metabolites such as ascofuranone and colletochlorin D. (3-Bromo-5-chloro-2,6-dimethoxy-p-tolyl)acetaldehyde was synthesized from orcinol in eight steps.This aldehyde was converted to 2-bromo-6-chloro-3,5-dimethoxy-4-(3-methyl-2-butenyl)toluene which was subsequently formylated to afford 3-chloro-4,6-dimetoxy-2-methyl-5-(3-methyl-2-butenyl)benzaldehyde.Although various demethylation procedures were tried, demethylation of both methoxy groups could not be accomplished.In our attempts to synthesize ascofuranone, (3-bromo-5-chloro-2,6-dimethoxy-p-tolyl)acetaldehyde was treated with isopropenylmagesium bromide to afford an unsteble allylic alcohol which was immediately subjected to the conditions of the "orthoacetate Claisen rearrangement" to give 2-bromo-6-chloro-4-3,5-dimethoxytoluene.This compound was then converted to 2-bromo-6-chloro-3,5-dimethoxy-4-toluene bromide in three steps.All attempts to carry out a Wittig reaction between this compound and 6,6-dimethyl-1,4,7-trioxaspironon-8-yl methyl ketone failed.Other coupling methods were equally unsuccesful.
