[Polycyclic azines with heteroatoms in the 1- and 3-position. 40. Synthesis of heterocyclic immunomodulators. 3. Synthesis of n-1 substituted 3-(2-mercaptoethyl)quinazoline-2,4-(1H,3H)-diones from bis(2-(2-aminobenzoylamino)ethyl)disulfane and testing of immunostimulant activity].
A 3-step synthesis, starting from substituted isatoic anhydride was used to prepare substituted 3-(2-mercaptoethyl)quinazoline-2,4(1H,3H)-diones 4. Reaction of 1 with cystamine afforded bis[2-(2-amino-benzoyl-amino)ethyl]disulfanes 2. Reaction of 2 with ethyl chloroformate and subsequent reduction of the heterocyclic disulfanes 3 gave mercaptoethylquinazoline-2,4-diones 4a-f.N-1 methyl and benzyl substituted derivatives 4b and 4c, respectively, show immuno-stimulating activity in various tests.
Gütschow
M
M
Institut für Pharmazie, Universität Leipzig, Leipzig, Germany.
Drössler
K
K
Leistner
S
S
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D006462:Hemolytic Plaque Technique; D006968:Hypersensitivity, Delayed / Q000188:drug therapy; D051379:Mice; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology
D000276:Adjuvants, Immunologic; D011799:Quinazolines
Mehrcyclische Azine mit Heteroatomen in 1- und 3-Stellung. 41. Mitt.; Synthese heterocyclischer Immunmodulatoren. 3. Mitt.: Darstellung von N-1-substituierten 3-(2-Mercaptoethyl)chinazolin-2,4(1H,3H)-dionen über Bis[2-(2-amino-benzoylamino)ethyl]disulfane und Prüfung auf immunstimulatorische Wirksamkeit.