[Imidazo(2,1-b)thiazole XII derivatives. Synthesis and research of immunoactivity in vitro on human T lymphocyte of 3-aroylmethyl and 2-aroyl-3-methyl(aryl)-5,6-dihydroimidaz o(2,1-b)thiazoles].
To estimate the influence of aryl group position on the immunostimulant properties of imidazo[2,1-b]thiazole derivatives, several compounds were obtained and tested, versus tetramisole hydrochloride, on the mobilisation of CD2 receptor by human T lymphocyte. The synthesis use the action of monobrominated beta-diketones on the 2-mercaptoimidazoline. So, 1-aryl-4-bromobutane-1,3-diones lead to 3-aroylmethyl-5,6-dihydroimidazo[2,1-b]thiazoles 4. Same, 1-aryl-2-bromobutane-1,3-diones and 1,3-diaryl-2-bromopentane-1,3-diones give respectively 3-aroyl-2-methyl-5,6-dihydroimidazo[2,1-b]thiazoles 5 and 3-aroyl-2-aryl-5,6-dihydroimidazo[2,1-b]thiazoles 6. Better yields are obtained when the reaction presents two steps. The first one, realized in acetone at room temperature, leads to an intermediate S-substituted 4,5-dihydroimidazole which, in second step, is cyclized in imidazo[2,1-b]thiazole compound via an unisolated carbinolamine. This one explains the univocal formation of 5 derivatives and the feasible blending in case of 6. The immunoactivity of several imidazothiazoles 4, 5 and 6 is lower that them of 6-aryl substituted compounds and particularly that the levamisole which is the reference product in this series.
Robert
J F
JF
Equipe de Chimie thérapeutique, UFR des Sciences Médicales et Pharmaceutiques, Besançon.
Hassanine
A
A
Harraga
S
S
Seilles
E
E
D000276:Adjuvants, Immunologic / Q000494:pharmacology*; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D013601:T-Lymphocytes / Q000276:immunology*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
D000276:Adjuvants, Immunologic; D007093:Imidazoles; D013844:Thiazoles
Dérivés de l'imidazo[2,1-b]thiazole XII. Synthèse et recherche d'une immunoactivité in vitro sur le lymphocyte T humain de 3-aroylméthyl et de 2-aroyl-3-méthyl(aryl)-5,6-dihydroimidazo[2,1-b]thiazoles.