Five chiral arylglycerol ethers 2-R-C₆H₄-O-CH₂CH(OH)CH₂OH (R = OMe, OEt, OPrⁿ, OPrⁱ, OBu^t) have been prepared in racemic and enantiopure form.The m.ps. and enthalpies of fusion of every species were measured by differential scanning calorimetry.Binary phase diagrams were reconstructed for the whole family, the entropies of the mixing of the enantiomers in the liquid state, and Gibbs free energy of formation of the racemic compound, as well as Pettersson i-values were derived from the thermal data.The differences in the phase behavior of the investigated compounds were associated with the conformations of the alkoxy fragments.

01 Jan 1960·Chemical and Pharmaceutical Bulletin

Researches on Chemotherapeutic Drugs against Viruses. XXXI. Synthesis and Antiviral Effect of 3-(Alkoxyphenoxy)-1, 2-propanediols on Respiratory Virus.

Author: Koibuchi, Hiroko ; Takahashi, Kiyoshi ; Toyoshima, Shigeshi ; Seto, Yoshiko ; Ueda, Takeo ; Muraoka, Masako

To find chemotherapeutic agents for influenza and adenoviruses, the title compounds (I) were synthesized.In general, (a) 0.1 mole each ROC₅H₄OH and ClCH₂CH(OH)CH₂OH was stirred 6 hrs. on a steam bath in the presence of EtONa in EtOH and the mixture after removal of EtOH extracted with ether.(b). HOC₆H₄OCH₂CH(OH)CH₂OH was refluxed 7 hrs. with RCl in the presence of EtONa or (c) in the presence of K₂CO₃ in Me₂CO (RO and its position, method, % yield, m.p., and b.p. I given): m-HO, a, 52, 93°, b₃ 208-10°;m-MeO, a, 49, 74-6°, b_2.5 175°;m-EtO, a, 51, 58-9°, b₃ 172-3°;m-PrO, a, 58, 61-2°, b_2.5 180-2°;m-BuO, a, 37, 76-7°, b₃ 187-90°;m-C₅H₁₁O, a, 39, 74-5°, b₂ 188-90°;m-C₆H₁₃O, a, 50, 78-80°, b₂ 197-9°;m-C₈H₁₇O, a, 39, 81-3°, b_2.5 219-20°; m-C₁₀H₂₁O, a, 49, 92-3°, b₂ 223-5°; m-C₁₂H₂₅O, a, 50, 95-6°, b₂ 226°; p-HO, a, 50, 111-13°, b₄ 217-19°; p-MeO, a, 35, 80-1°, b_2.5 176-8°; p-EtO, a, 68, 83-5°, b_2.5 172-4°; p-PrO, a, 58, 90-2°, b_2.5 182-3°; p-BuO, a, 52, 88-90°, b_2.5 182-4°; p-C₅H₁₁O, a, 54, 83-4°, b₃ 200-2°; p-C₆H₁₃O, b, 60, 71-3°, -; p-C₈H₁₇O, b, 76, 86-7°, -; p-C₁₀H₂₁O, b, 75, 96-8°, -; p-C₁₂H₂₅O, b, 73, 101-3°, -; o-HO, a, 56, 87-8°, b_2.5 218-20°; o-MeO, -, 50, 80-2°, b₄ 157-9°; o-EtO, c, 58, 64-6°, b_2.5, 161-3°; o-PrO, c, 68, 60-2°, b_2.5 170-2°; o-BuO, c, 70, 69-70°, b_2.5 185-7°; o-C₅H₁₁O, c, 67, 55-6°, b_2.5 180-2°; o-C₆H₁₃O, c, 51, 61-3°, b_2.5 184-6°; o-C₈H₁₇O, c, 57, 78-9°, -; o-C₁₀H₂₁O, c, 55, 67-8°, -; and o-C₁₂H₂₅O, c, 56, 63-5°, -.Among these derivatives I(RO = m-C₁₂H₂₅O) showed a fairly inhibitory effect on the multiplication of the PR-8 strain of influenza virus in chorioallantoic membrane culture.I (RO = o-C₆H₁₃O, o-C₈H₁₇O, and p-C₁₂H₂₅O) were effective on some strains of adenovirus, but experiments showed such effectiveness probably due to inhibition of viral multiplication.

01 Mar 1953·Experimental Biology and Medicine

Hemolytic Action of Water Soluble Compounds Related to Mephenesin

Article

Author: F. M. Berger ; B. J. Ludwig ; C. V. Hubbard

Mephenesin; 3-phenoxy-, 3-(o-methoxyphenoxy)-, 3-(o-ethoxyphenoxy)-, 3-(2,6-dimethoxyphenoxy)-, 3-benzyloxy-, 3-(p-methylbenzyloxy)-, 3-(o-methoxybenzyloxy)-, 3-(2-phenylethoxy)-, and 3-(1-phenylethoxy)-l,2-propanediol; 2-phenoxy-, 2-(m-toloxy)-, 2-(o-methoxyphenoxy)-, 2-(o-ethoxyphenoxy)-, and 2-benzyloxy-1,3-propanediol; and 1-ethoxy-3-isopropoxy-2-propanol were compared.Mephenesin was the most potent paralyzing agent in mice and also had the strongest hemolytic action on washed rabbit erythrocytes in vitro.The 3-(o-ethoxyphenoxy)-1,2-propanediol approached mephenesin in paralyzing action but had only about half as much hemolytic activity.The actions of the other compounds were weaker.No significant correlation between the solubility of the compounds, their water-oil partition ratios, and their paralyzing and hemolytic action was evident.

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