73502-04-2Relevant academic research and scientific papers
Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum
Murata, Chihiro,Ogura, Tetsuhiro,Narita, Shuhei,Kondo, Anna P.,Iwasaki, Natsumi,Saito, Tamao,Usuki, Toyonobu
, p. 1428 - 1433 (2016/02/19)
4-Methyl-5-pentylbenzene-1,3-diol (MPBD) is a secondary metabolite of SteelyA polyketide synthase, which controls cell aggregation and spore maturation of Dictyostelium discoideum. In this study, chemical synthesis of MPBD and its derivatives was achieved. Structure-activity relationship (SAR) studies for antimicrobial activities against Escherichia coli and Bacillus subtilis were also conducted.
Structure revision of medermycin/lactoquinomycin a and of related C-8 glycosylated naphthoquinones.
Leo, Pierre-Marc,Morin, Christophe,Philouze, Christian
, p. 2711 - 2714 (2007/10/03)
[reaction: see text] On the basis of chemical and spectral data, the structure of the medermycin/lactoquinomycin A has been revised, which has also led to the revision of related C-glycosylated naphthoquinone antibiotics such as lactoquinomycin B, menoxymycins A and B, G15-F, and G15-G.
Some evidence in favour of an electron transfer mechanism in the TiO2 photosensitized oxidation of benzyl derivatives in aqueous media
Ranchella, Michele,Rol, Cesare,Sebastiani, Giovanni V.
, p. 311 - 315 (2007/10/03)
The structure and/or distribution of products from the TiO2-sensitized photooxidation of some benzyl derivatives in aerated and/or deaerated aqueous media and in the presence of Ag2SO4 are reported. The results suggest that the single electron transfer process from the substrate to the photogenerated hole, previously proposed in CH3CN, should also be operative on gradually going from aqueous CH3CN to pure water.
CYCLISATION DE DIARYLALCANES EN MILIEU SUPERACIDE: SYNTHESE DE CETONES TRICYCLIQUES A METHYLE ANGULAIRE ET MECANISME DE LEUR ISOMERISATION
Berrier, C.,Jacquesy, J. C.,Gesson, J. P.,Renoux, A.
, p. 1983 - 1994 (2007/10/02)
Cyclisation of redily available diaryl-1,2 ethanes 1-4 proceeds in SbF5-HF at 0oC to yield tricyclic phenantrenones 5,6,7 and 11 bearing an angular methyl group.This process implies the electrophilic attack of the more basic aromatic ring, reacting through its disprotonated form (on the oxygen and the meta carbon atom) on the second aromatic ring.Isomerization of these primary products may be observed (to give ketones 8,9,10 from 3 and 12 from 4) and it has been demonstrated by the use of specifically deuterated 3d that it involves stereospecific 1,2 hydride (or deuteride) shifts, without exchange.
Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 3. Synthesis, estrogen receptor binding affinity, and evaluation of antiestrogenic and mammary tumor inhibiting activity of 2,2'-disubstituted butestrols and 6,6'-disubstituted metabutestrols
Hartmann,Heindl,Schwarz,Schonenberger
, p. 819 - 824 (2007/10/02)
The syntheses of symmetrically 2,2'-disubstituted butestrols [meso-2,3-bis(4-hydroxyphenyl)butanes] and of 6,6'-disubstituted metabutestrols [meso-2,3-bis(3-hydroxyphenyl)butanes] are described [2,2'-substituents: H (1), OH (2), F (3), Cl (4), Br (5), CH3 (6), and C2H5 (7); 6,6'-substituents: H (8), OH (9), Cl (10), and CH3 (11)]. Compounds 1-11 were obtained by reductive coupling of the corresponding 1-phenylethanols with TiCl3/LiAlH4 and separation of the meso diastereomers. The binding affinity of the test compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. With the exception of 9, all other compounds showed remarkably high relative binding affinity (RBA) values between 1.0 and 29% that of estradiol. Compounds 3 and 6 (RBA values: 15 and 29), as well as 10 and 11 (1.7 and 5.2), exceeded those of the corresponding unsubstituted compounds 1 and 8 (12 and 1.0). The compounds exhibited strong (3, 4, 6, and 7), moderate (1, 2, and 10), weak (11), or no (8) estrogenic activity in the uterine weight test of the immature mouse. Compounds 1, 2, 8, 10 and 11 showed antiestrogenic activity inhibiting the estrone-stimulated uterine growth (25-35% inhibition). Compound 11 led to a significant inhibition of the tumor growth when tested on the 9,10-dimethyl-1,2-benzanthracene induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat.
