Synthesis and antileishmanial activity of (1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives.
(1,3-Benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives were synthesized via a procedure based on the Ullman reaction and were assessed for their in vitro antileishmanial and anti-HIV activities. Two derivatives, 4-(6-nitro-benzothiazol-2-ylamino)-10H-acridin-9-one and 1-(6-amino-benzothiazol-2-ylamino)-10H-acridin-9-one, revealed a selective antileishmanial activity, mainly due to amastigote-specific toxicity. Results suggested that:the addition of a benzothiazole group on a parent amino-9-(10H)-acridinone ring could enhance antileishmanial abilities, the presence of a 6-amino-benzothiazole group on position 2 amino chain or a 6-nitro-benzothiazole group on position 4 amino chain was essential for specific anti-amastigote properties.
Laboratoire de parasitologie, hygiène et zoologie, faculté de pharmacie, université de Marseille, 27, bd. Jean Moulin, 13385 Marseille cedex 5, France.
Florence
F
Delmas
Antonio
A
Avellaneda
Carole
C
Di Giorgio
Maxime
M
Robin
Erik
E
De Clercq
Pierre
P
Timon-David
Jean-Pierre
JP
Galy
D000166:Acridines / Q000138:chemical synthesis* / Q000494:pharmacology*; D054831:Acridones; D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D052160:Benzothiazoles; D006801:Humans; D018314:Leishmania infantum / Q000187:drug effects* / Q000254:growth & development; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
D000166:Acridines; D054831:Acridones; D000981:Antiprotozoal Agents; D052160:Benzothiazoles; D013844:Thiazoles; C041300:acridone; C005465:benzothiazole