4161-22-2Relevant articles and documents
Ultrasonic Relaxations in Aqueous Solutions of Alcohols and the Balance between Hydrophobicity and Hydrophilicity in the Solutes
Nishikawa, Sadakatsu,Udea, Masayuki
, p. 3539 - 3544 (1993)
3-Propoxy-1-propanol was synthesized with 1,3-propanediol, anhydrous potassium carbonate, and propyl bromide, and the ultrasonic absorption coefficents in the frequency range from 6.5 to 220 MHz, sound velocity, and density were measured in the aqueous solutions at various concentrations.It was speculated that a double relaxational equation of the Debye type is appropriate to represent the absorption data in the concentration range from 1.0 up to 5.0 mol dm-3 while a single one is fitted in those less than 1.0 down to 0.79 mol dm-3.For explaining the ultrasonic relaxation phenomena, the analysis was carried out with a reaction model associated with solute-solvent interaction and with an aggregation reaction of the solute expressed as A + B AB AB*.From the concentration dependence of the relaxation frequencies, the rate and the thermodynamic parameters were evaluated for the two reactions.The propoxy group in alcohol molecules was evaluated to have a relatively high hydrophobic character, and it plays an important role for stabilizing the water structure.From the comparison of the present results with those for other alcohol solutions reported previously, the effects of methoxyl, ethoxyl, and propoxyl groups on the water structure were systematically considered and a linear relationship was found between the standard free energy change of two-state, i.e. hydrogen-bonded and non-hydrogen-bonded, water in the solutions and the carbon number of the alkoxyl groups.It was shown quantitatively that the methoxyl group acts as a structure breaker for water, the ethoxyl group influences the water structure slightly, and the propoxyl group promotes the structure.
1,3-Disubstituted ureas functionalized with ether groups are potent inhibitors of the soluble epoxide hydrolase with improved pharmacokinetic properties
Kim, In-Hae,Tsai, Hsing-Ju,Nishi, Kosuke,Kasagami, Takeo,Morisseau, Christophe,Hammock, Bruce D.
, p. 5217 - 5226 (2008/03/13)
Soluble epoxide hydrolase (sEH) is a therapeutic target for treating hypertension and inflammation. 1,3-Disubstituted ureas functionalized with an ether group are potent sEH inhibitors. However, their relatively low metabolic stability leads to poor pharmacokinetic properties. To improve their bioavailability, we investigated the effect of incorporating various polar groups on the ether function on the inhibition potencies, physical properties, in vitro metabolic stability, and pharmacokinetic properties. The structure-activity relationship studies showed that a hydrophobic linker between the urea group and the ether function is necessary to keep their potency. In addition, urea-ether inhibitors having a polar group such as diethylene glycol or morpholine significantly improved their physical properties and metabolic stability without any loss of inhibitory potency. Furthermore, improved pharmacokinetic properties in murine and canine models were obtained with the resulting inhibitors. These findings will facilitate the usage of sEH inhibitors in animal models of hypertension and inflammation.
A New Oxaanalog of Myristic Acid that Suppresses Replication of Human Immunodeficiency Virus
Vodovozova, E. L.,Mikhalev, I. I.,Rzhaninova, A. A.,Garaev, M. M.,Molotkovsky, Yul. G.
, p. 626 - 632 (2007/10/03)
A series of oxaanalogs of myristic acid were synthesized and tested for antiviral activity in MT4 cells infected with human immunodeficiency virus 1 (HIV-1).The synthesized acids have no toxic effect on uninfected MT4 cells at a concentration of 100μM. 14,14,14-Trifluoro-12-oxatetradecanoic acid substantially (by 75percent) inhibits the reproduction of HIV-1.Other compounds synthesized, (7Z)-13-, (9Z)-13-, and (7Z)-11-oxatetradecenoic acids, exhibit no antiviral effect.Key words: inhibitors of retroviruses; anti-HIV agents; protein N-myristoylation; mystoylCoA: protein-N-myristoyltransferase; myristic acid; oxaanalogs; inhibitors of virus-specific protein myristoylation
