42965-39-9Relevant academic research and scientific papers
Naphthalene anti-psoriatic agents
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, (2008/06/13)
Naphthalenes of the formula: STR1 wherein: m is 1 or 2; n is 1, 2, or 3; R1 is alkyl of one to seven carbon atoms or an optionally substituted phenyl; R2 is hydrogen, lower alkyl, lower alkoxy, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl, optionally substituted phenyl-lower-alkoxy, amino, lower alkylamino, lower dialkylamino, halo, cyano, hydroxy, or lower alkylthio are useful in relieving psoriasis.
Synthesis and Characterization of Crowned 1,4-Benzoquinones as Ionophore-Dienophile (Redox) Combined Systems: Double Interaction with Catecholamines and Tryptamine
Hayakawa, Kenji,Kido, Keiko,Kanematsu, Ken
, p. 511 - 520 (2007/10/02)
The crowned 1,4-benzoquinones (1) (15-crown-5) and (2) (18-crown-6) have been synthesized from pyrogallol (3) by: (1) the selective monobenzylation (4); (2) crown ether formation using a pyrocatechols (5) and (6); (3) debenzylation (7) and (8); and (4) oxidation to 1,4-benzoquinones.Both compounds (1) and (2) underwent smooth Diels-Alder reactions with cyclopentadiene (25 deg C), thebaine (80 deg C), and buta-1,3-diene (BF3*Et2O, 0 deg C).The cyclopentadiene adducts (11) and (12) were photochemically transformed into the cage compounds (13) and (14), while the thebaine adducts (15) and (16) were smoothly converted into the hydroquinone derivatives (17) and (18) by silicic acid.The butadiene adducts (19) and (20) were transformed into the crowned naphthoquinones (23) and (24) in high yields.The redox potentials of these crowned quinones in the presence of alkali-metal ions were studied by cyclic voltammetry.The specific interaction between compound (2) and tryptamine, dopamine, and homoveratrylamine via ion-binding and charge-transfer complex formation was evidenced by u.v. spectroscopic studies.
Synthesis and inhibitory activity of new ethylenedioxyquinones as analogs of coenzyme
Bowman,Wikholm,Boler,Bogentoft,Folkers
, p. 988 - 991 (2007/10/05)
A new series of analogs of coenzyme Q, 2,3 ethylenedioxy 5 hydroxy 6 alkyl 1,4 benzoquinones, was synthesized on the basis of the minor differences in the electronic and rotational nature between the 2,3 ethylenedioxy group and 2,3 dimethoxy groups. These differences could affect the redox potential of the 1,4 benzoquinone and, in turn, affect inhibitory activity. The 6 alkyl groups were farnesyl, phytyl, nonyl, decyl, pentadecyl, heptadecyl, and 5' (cyclohexyl)pentyl. The succinoxidase and DPNH oxidase systems of intact mitochondria from beef heart were used in tests for inhibition. The nonyl, decyl, pentadecyl, and farnesyl analogs showed inhibitions of less than 40%; and the phytyl, heptadecyl, and 5' (cyclohexyl)pentyl analogs showed inhibitions of about 50% in succinoxidase. All the analogs were less inhibitory in DPNH oxidase. 2,3 Dimethoxy 5 hydroxy 6 n pentadecyl 1,4 benzoquinone showed 91% inhibition at a concentration of 97 nmol of inhibitor/mg of mitochondrial protein, while 2,3 ethylenedioxy 5 hydroxy 6 n pentadecyl 1,4 benzoquinone exhibited only 37% inhibition at the higher concentration of 140 nmol of inhibitor/mg of mitochondrial protein in the succinoxidase system. Similarly, this 2,3 dimethoxyquinone was a more potent inhibitor in DPNH oxidase. 2,3 Dimethoxy 5 hydroxy 6 n pentadecyl 1,4 benzoquinone showed 91% inhibition at a concentration of 97 nmol of inhibitor/mg of mitochondrial protein, while 2,3 ethylenedioxy 5 hydroxy 6 n pentadecyl 1,4 benzoquinone exhibited only 37% inhibition at the higher concentration of 140 nmol of inhibitor/mg of mitochondrial protein in the succinoxidase system. Similarly, this 2,3 dimethoxyquinone was a more potent inhibitor in DPNH oxidase than the corresponding 2,3 ethylenedioxyquinone. Apparently, 2,3 dimethoxy groups are more favorable than the 2,3 ethylenedioxy group on the 5 hydroxy 6 alkyl 1,4 benzoquinone nucleus for inhibition of these two CoQ oxidases.
