Synthesis, analytical behaviour and biological evaluation of new 4-substituted pyrrolo[1,2-a]quinoxalines as antileishmanial agents.
An original series of 4-substituted pyrrolo[1,2-a]quinoxaline derivatives, new structural analogues of Galipea species quinoline alkaloids, was synthesized from various substituted 2-nitroanilines via multistep heterocyclizations and tested for in vitro antiparasitic activity upon Leishmania amazonensis and Leishmania infantum strains. Structure-activity relationships enlighten the importance of the 4-substituted alkenyl side chain on the pyrrolo[1,2-a]quinoxaline moiety to modulate the antileishmanial activity.
Guillon
Jean
J
EA 2962-Pharmacochimie, UFR des Sciences Pharmaceutiques, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux Cedex, France. Jean.Guillon@chimphys.u-bordeaux2.fr
Forfar
Isabelle
I
Mamani-Matsuda
Maria
M
Desplat
Vanessa
V
Saliège
Marion
M
Thiolat
Denis
D
Massip
Stéphane
S
Tabourier
Anais
A
Léger
Jean-Michel
JM
Dufaure
Benoit
B
Haumont
Gilbert
G
Jarry
Christian
C
Mossalayi
Djavad
D
D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D007891:Leishmania / Q000187:drug effects*; D007963:Leukocytes, Mononuclear / Q000187:drug effects; D008958:Models, Molecular; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000981:Antiprotozoal Agents; D011810:Quinoxalines