Synthesis and transformations of 2,6-bis(1,1-dimethylethyl)-4-[2-(thiazolyl)ethenyl]phenols

(Thiazolylethenyl)phenols were prepared as potential antiinflammatories by reaction of thiazole 4- and 5-acetic acid derivatives with 3,5-di-tert-butyl-4-hydroxybenzaldehyde. Alternatively, an arylethenyl methyl ketone was brominated and the bromoketone product reacted with methyl dithiocarbamate, ammonium dithiocarbamate, or thiourea.

[1]  D. Ortwine,et al.  Styrylpyrazoles, styrylisoxazoles, and styrylisothiazoles. Novel 5-lipoxygenase and cyclooxygenase inhibitors. , 1991, Journal of medicinal chemistry.

[2]  A. G. Graham,et al.  Antiinflammatory 2,6-di-tert-butyl-4-(2-arylethenyl)phenols. , 1989, Journal of medicinal chemistry.

[3]  I. Katsumi,et al.  Studies on styrene derivatives. II. Synthesis and antiinflammatory activity of 3,5-di-tert-butyl-4-hydroxystyrenes. , 1986, Chemical & pharmaceutical bulletin.

[4]  I. Katsumi,et al.  Studies on styrene derivatives. I. Synthesis and antiinflammatory activities of alpha-benzylidene-gamma-butyrolactone derivatives. , 1986, Chemical & pharmaceutical bulletin.

[5]  L. Brandsma,et al.  An Efficient Synthesis of 1,3-Thiazole , 1985 .

[6]  H. Homma,et al.  Synthesis and anti-inflammatory activity of 2,6-di-tert-butylphenols with a heterocyclic group at the 4-position. III. , 1984, Chemical & pharmaceutical bulletin.

[7]  W. C. Still,et al.  Rapid chromatographic technique for preparative separations with moderate resolution , 1978 .

[8]  C. V. Winder,et al.  A sensitive method for the comparative bioassay of nonsteroidal anti-inflammatory compounds in adjuvant-induced primary inflammation in the rat. , 1975, The Journal of pharmacology and experimental therapeutics.

[9]  P. Ariés,et al.  Death inside out , 1974 .

[10]  J. J. D'amico,et al.  Derivatives of Ethyl 2-Mercapto-4-thiazoleacetate and Rhodanine , 1955 .

[11]  P. L. Southwick,et al.  4-STYRYLTHIAZOLES. SYNTHESES AND RELATIONSHIPS AMONG ULTRAVIOLET ABSORPTION SPECTRA , 1954 .

[12]  Y. Hara,et al.  The synthesis of some thiazole derivatives from levulinic acid. , 1954, Pharmaceutical Bulletin.