19754-21-3Relevant 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)
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.
Facile synthesis of 5,6-dimethoxy-1-tetralone
Lahiri, Saswata,Ramarao,Rao, B. Venkateswara,Rao, A.V. Rama,Chorghade, Mukund S.
, p. 71 - 72 (1999)
A facile synthesis of 5,6-dimethoxy-1-tetralone, a key intermediate in the synthesis of an antidepressant compound, ABT-200, was developed from the inexpensive starting material guaiacol.
Crossing the Boundaries between Marine and Muguet: Discovery of Unusual Lily-of-the-Valley Odorants Devoid of Aldehyde Functions
Jordi, Samuel,Kraft, Philip
, (2018/06/04)
Since 6-isopropyl- (11) and 6-isobutyl-2H-benzo[b][1,4]dioxepin-3(4H)-one (12) instead of the expected marine odor had been reported to possess lily-of-the-valley notes, albeit weaker than benchmark odorants, the influence of a cyclopropyl ring instead of
Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, trichoplusia ni: Potential insect behavior control agents
Akhtar, Yasmin,Yu, Yang,Isman, Murray B.,Plettner, Erika
, p. 4983 - 4991 (2011/08/06)
The antifeedant, oviposition deterrent, and toxic effects of individual dialkoxybenzene compounds/sets and of hydroxy- or alkoxy-substituted allylbenzenes, obtained through Claisen rearrangement of substituted allyloxybenzenes, were assessed against the cabbage looper, Trichoplusia ni, in laboratory bioassays. Most of the compounds/sets strongly deterred larval feeding, with some exhibiting mild toxic and oviposition deterrent effects as well. Some of the compounds/sets were more active than the commercial insect repellent, DEET (N,N-diethyl-m-toluamide), as both feeding and oviposition deterrents against the cabbage looper. On the basis of the obtained oviposition data a general hypothesis was proposed regarding the oviposition sites: one binding mode with the alkyl and allyl groups on the same side of the benzene ring resulted in deterrence, the other with alkyl and allyl groups on opposite sides of the benzene ring resulted in stimulation. The results suggest some structure-activity relationships useful in improving the efficacy of the compounds and designing new, nontoxic insect control agents for agriculture.
Deprotonative metalation of substituted aromatics using mixed lithium-cobalt combinations
Dayaker, Gandrath,Chevallier, Floris,Gros, Philippe C.,Mongin, Florence
experimental part, p. 8904 - 8910 (2011/01/04)
The deprotonation of anisole was attempted using different homo- and heteroleptic TMP/Bu mixed lithium-cobalt combinations. Using iodine to intercept the metalated anisole, an optimization of the reaction conditions showed that in THF at room temperature 2 equiv of base were required to suppress the formation of the corresponding 2,2′-dimer. The origin of the dimer was not identified, but its formation was favored with allyl bromide as electrophile. The metalated anisole was efficiently trapped using iodine, anisaldehyde, and chlorodiphenylphosphine, and moderately employing benzophenone, and benzoyl chloride. 1,2-, 1,3-, and 1,4-dimethoxybenzene were similarly converted regioselectively to the corresponding iodides. It was observed that 2-methoxy- and 2,6-dimethoxypyridine were more prone to dimerization than the corresponding benzenes when treated similarly. Involving ethyl benzoate in the metalation-iodination sequence showed that the method was not suitable to functionalize substrates bearing reactive functions.
Molybdenum- and tungsten-catalyzed allylation of aromatic compounds with allylic esters and alcohols
Shimizu, Isao,Sakamoto, Toshiaki,Kawaragi, Saeko,Maruyama, Yooichiro,Yamamoto, Akio
, p. 137 - 138 (2007/10/03)
A novel method to substitute aromatic compounds with allylic groups using oxygen-containing allylic compounds in the presence of molybdenum or tungsten carbonyls under neutral conditions has been developed. The method is applicable to one step synthesis of methyl eugenol.
STRUCTURE-ACTIVITY RELATIONSHIPS OF PHENYLPROPANOIDS AS GROWTH INHIBITORS OF THE GREEN ALGA SELENASTRUM CAPRICORNUTUM
Greca, Marina Della,Monaco, Pietro,Pollio, Antonino,Previtera, Lucio
, p. 4119 - 4124 (2007/10/02)
Twenty-seven commercial or synthetic phenylpropanoids have been tested in broth against the unicellular alga Selenastrum capricornutum.The antialgal activity seems to be linked to the number as well as to the position of the methoxyl group in the molecule.A slight effect of the side chain substitution was also observed. Key Word Index - Selenastrum capricornutum; allelochemicals; phenylpropanoids.
REACTION OF o-BENZOQUINONE BISACETALS WITH ORGANOLITHIUMS. A NOVEL ROUTE TO SUBSTITUTED VERATROLES
Kikuchi, Yoshiyuki,Hasegawa, Yoko,Matsumoto, Masakatsu
, p. 2199 - 2202 (2007/10/02)
Substituted veratroles were easily obtained by the reaction of o-benzquinone bisacetals with organolithiums.
