54289-74-6Relevant articles and documents
VASCULAR ADHESION PROTEIN-1 (VAP-1) MODULATORS AND THERAPEUTIC USES THEREOF
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Paragraph 0264, (2020/01/24)
Disclosed herein are small molecule Vascular Adhesion Protein- 1 (VAP-1) modulator compositions, pharmaceutical compositions, the use and preparation thereof.
Synthesis and biological activity of 5-(4-methoxyphenyl)-oxazole derivatives
Yamamuro, Daisuke,Uchida, Ryuji,Ohtawa, Masaki,Arima, Shiho,Futamura, Yushi,Katane, Masumi,Homma, Hiroshi,Nagamitsu, Tohru,Osada, Hiroyuki,Tomoda, Hiroshi
supporting information, p. 313 - 316 (2015/04/13)
5-(4′-Methoxyphenyl)-oxazole (MPO), originally reported as a synthetic compound, was isolated from fungal culture broth as an inhibitor of hatch and growth of Caenorhabditis elegans. Nineteen MPO derivatives were chemically synthesized, but showed no effect on C. elegans hatch and growth. These findings strongly suggested that the whole structure of MPO is essential for anti-C. elegans activity.
Benzyne-Oxazole Cycloadducts: Isolation and Retro-Diels-Alder Reactions
Whitney, Scott E.,Winters, Michael,Rickborn, Bruce
, p. 929 - 935 (2007/10/02)
A literature procedure for generating benzyne from 1-aminobenzotriazole and lead tetraacetate was modified by the use of two syringe pumps to effect simultaneous addition through opposing ports of a three-neck flask.Applied to the reaction of benzyne with 4-phenyloxazole at 0 deg C, this modification resulted in essentially quantitative formation of cycloadduct.Retro-Diels-Alder expulsion of benzonitrile with concurrent formation of isobenzofuran occurred when the adduct was heated.The sequence constitutes a useful method of preparation of isobenzofuran, which may be utilized in situ or isolated as a solution for subsequent application.Benzyne cycloadducts were also prepared from 4-(4-nitrophenyl)- and 4-(4-methoxyphenyl)oxazoles, in order to assess the effect of remote substituents on the retro-Diels-Alder reaction.First-order rate constants were determined at three temperatures in the range of 40-70 deg C.The order of reactivity was p-NO2 > p-H > p-OMe; the substituent effects were small, with a factor 4 separating the p-NO2 from p-OMe rate.All three substrates exhibited small ΔS(excit.) values.Expulsion of the nitrile is believed to occur as a concerted reaction with little charge development.The modified benzyne procedure was also applied to 2,5-diphenyloxazole, at 0 and -78 deg C.Oxazole was recovered (59percent and 43percent at the higher and lower temperature, respectively).No bis(benzyne) adduct was formed, showing that 1,3-diphenylisobenzofuran is not generated during the course of the reaction.The 1:1 benzyne-diphenyloxazole cycloadduct is not observed in the crude product of the0 deg C reaction, but an absorption at 6.09 ppm in the NMR spectrum of crude product from the -78 deg C reaction is attributed to this material.The latter crude product on standing at room temperature forms the isobenzofuran.Both reaction mixtures form 1,3-diphenylisobenzofuran by another mechanism involving a second intermediate.This more polar intermediate, which appears to be the major product at 0 deg C, slowly gives 1,3-diphenylisobenzofuran.The overall more efficient cycloaddition at - 78 deg C is attributed to entropy effects, which tend to favor Diels-Alder over other second-order reactions as the temperature is lowered.
