Chemical and Pharmaceutical Bulletin p. 1076 - 1083 (1994)
Update date:2022-08-03
Topics:
Refouvelet
Harraga
Nicod
Robert
Seilles
Couquelet
Tronche
A series of 6,8-dioxo-3-thia-1,7-diazabicyclo[3.3.0]octanes and a series of 6,8-dioxo-3-thia-1,7-diazabicyclo[3.3.0]octane 2-spiro derivatives were synthesized from L-(-)-R-cysteine ethyl ester in two steps. The synthetic route involved condensation of the amino acid with an appropriate aldehyde or ketone, then a further condensation of the resultant ethyl thiazolidine-4- carboxylate with an isocyanate or an isothiocyanate. The proliferative response to human lymphocyte mitogen (phytohemagglutinin) was used as a primary screening assay for most of the thiadiazabicyclic compounds in comparison with levamisole. Furthermore, the most active compounds were tested for ability to release soluble receptors (sRIL-2) after mitogenic stimulation of T cells and for ability to activate macrophage oxidative metabolism measured by chemiluminescence. Most compounds were active in all three tests and some showed dose-dependent activity.
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Doi:10.1135/cccc19942069
(1994)Doi:10.1016/j.jorganchem.2008.04.038
(2008)Doi:10.1016/S0040-4039(00)84265-3
(1986)Doi:10.1021/je00047a039
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(1995)Doi:10.1021/jo00106a021
(1995)
