Synthesis of N-acridinyl-N'-alkylguanidines: dramatic influence of amine to guanidine replacement on the physicochemical properties.
Transformation of aminoacridines into N-acridinyl-N'-alkylguanidines is described. The chosen procedure allows introduction of pendent substituents (exemplified by N,N-dimethylaminopropyl chain) into key acridinyl thioureas, thus opening the way to structural diversity. Spectroscopic study and pK(a) determination show that the presence of the strongly basic guanidine has a dramatic influence on the ionization of the acridine nucleus by lowering the pk(a) value down to 4.49.
Zeghida
Walid
W
Département Chimie Moléculaire, UMR5250 CNRS-University Joseph Fourier, BP53, 38041 Grenoble Cedex 9, France.
Debray
Julien
J
Michel
Carine
C
Milet
Anne
A
Dumy
Pascal
P
Demeunynck
Martine
M
D000588:Amines / Q000737:chemistry*; D000609:Aminoacridines / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D015195:Drug Design; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D000588:Amines; D000609:Aminoacridines; D006146:Guanidines