3813-01-2Relevant academic research and scientific papers
BICYCLIC ARYL AND HETEROARYL COMPOUNDS FOR THE TREATMENT OF METABOLIC DISORDERS
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Page/Page column 21; 8, (2009/01/20)
Compounds of formula (I): or pharmaceutically acceptable salts thereof, are opioid receptor modulators, e.g. mu- opioid receptor antagonists, neutral antagonists or inverse agonists, and are useful for the treatment of metabolic disorders including obesity.
Naphthyloxy acetic acid derivatives and a pharmaceutical composition comprising them as an active ingredient
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Referential example 10, (2010/11/29)
The naphthyloxyacetic acid derivatives of the formula (I) wherein A is H, -(alkylene)COOR1, -(alkylene)CONR2R3, -(alkylene)OH, -(alkylene)tetrazole, -(alkylene)CN; E is single bond or alkylene; G is —S—, —SO—, —SO2—, —O— or —NR4—; L is alkylene, —(CH2)m—CH═CH—(CH2)n— or —(CH2)x—CH(OH)—(CH2)y—; M is phenyl, phenyl(thio, oxy, amino), diphenylmethyl, diphenylmethyl(thio, oxy, amino), and pharmaceutical composition comprising them as an active ingradient. The compounds of the formula (I) can combine PGE2receptor and exhibit the activity to antagonize or agonize for PGE2receptor. Therefore, they are useful as anti-hyperlipemia, for the prevention of abortion, for analgesics, as antidiarrheals, sleep inducer, diuretic, anti-diabetes, abortient, cathartics, antiulcer, anti-gastritis or antihypertensive etc.
13C NMR investigation of electronic interactions in 5-substituted 1-naphthonitriles
Schuster, Ingeborg I.
, p. 301 - 310 (2007/10/03)
Carbon-13 NMR chemical shifts of 5-Z-substituted 1-naphthonitriles (1; Z = H, F, Cl, Br, NH2, NMe2, CN, NO2, OMe, CHO, CO2Me) in deuteriochloroform and in neat trifluoroacetic acid (TFA) are reported. The CN carbon shifts are found to correlate well with the dual substituent parameters (DSPs). Negative values of the transmission coefficients in the DSP correlation give evidence of a reverse substituent electronic effect, which is associated with variations in π polarization of the CN multiple bond, due primarily to differences in the through-space field effects of the various Z. The effect diminishes for 1 in neat TFA because of the greater contribution of dipolar ArC+=N- to the resonance hybrid. Deviations of the aromatic carbon shifts from substituent chemical shift additivities are small, yet show distinct patterns for many of the carbon resonances. The deviations of the C-1 - CN ipso carbon shifts of 1 in neutral solvents and in TFA correlate roughly with the DSPs. They are attributable to changes in charge density at C-1 that arise as a consequence of substituent-induced changes in the polarity of the CN bond. The greater than expected shielding that is observed for the C-6 and C-8 resonances accords with reduced electron withdrawal by +R substituents and increased mesomeric activity by electron-donating groups, Z, in response to the CN-induced charge depletion within the adjacent aromatic ring. From the location of data for 5-methoxy-1-naphthonitrile (1; Z = OMe) in the chemical shift correlations of 1 in neat TFA, one can conclude that the methoxy group of this compound, unlike that of 1-methoxynaphthalene itself, is not significantly hydrogen-bonded by TFA.
Photoexcited proton transfer from enhanced photoacids
Tolbert, Laren M.,Haubrich, Jeanne E.
, p. 10593 - 10600 (2007/10/02)
Naphthols with electron-withdrawing groups such as cyano or methanesulfonyl at C-5 and C-8 exhibit greatly enhanced photoacidity. This increase in photoacidity enables the substituted naphthols to undergo excited-state proton transfer (ESPT) in alcohols and Me2SO in the absence of water. In aqueous tetrahydrofuran solution, efficient proton transfer to water occurs at much lower water concentrations than with the parent naphthol, and the kinetics of proton transfer indicate that a smaller water cluster is involved.
