Annelated pyrrolo-pyrimidines from amino-cyanopyrroles and BMMAs as leads for new DNA-interactive ring systems.
The efficient one-pot synthesis of several new tricyclic systems of type 1 and 2, obtained from the reaction of substituted 2-amino-3-cyanopyrroles and 3-amino-4-cyanopyrroles with BMMAs, is reported. The duration and yields of the reaction strongly depend on the reactivity of the starting pyrrole and on the size of the ring to be formed. Mechanist features of the reaction were investigated and proposed by studying also the reactivity of a 3-aminopyrrole-2,4-dicyano substituted. The method reported represents the first example of the use of BMMA reagents in combination with pyrrole derivatives and allows an easy and versatile entry to a large number of hitherto unknown pyrrolo-pyrimidines further annelated with nitrogen heterocycles of different sizes. These new polycondensed heterocycles possess the requisite to interact with DNA.
Lauria
Antonino
A
Dipartimento Farmacochimico, Tossicologico e Biologico, Università di Palermo Via Archirafi 32, 90123 Palermo, Italy.
Bruno
Marcella
M
Diana
Patrizia
P
Barraja
Paola
P
Montalbano
Alessandra
A
Cirrincione
Girolamo
G
Dattolo
Gaetano
G
Almerico
Anna Maria
AM
D004247:DNA / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013057:Spectrum Analysis
D011743:Pyrimidines; D011758:Pyrroles; D004247:DNA