title: Synthesis of N-acridinyl-N'-alkylguanidines: dramatic influence of amine to guanidine replacement on the physicochemical properties.
abstract: 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.
authors.affiliation: Département Chimie Moléculaire, UMR5250 CNRS-University Joseph Fourier, BP53, 38041 Grenoble Cedex 9, France.
authors.forename: Walid
authors.initials: W
authors.lastname: Zeghida
authors.forename: Julien
authors.initials: J
authors.lastname: Debray
authors.forename: Carine
authors.initials: C
authors.lastname: Michel
authors.forename: Anne
authors.initials: A
authors.lastname: Milet
authors.forename: Pascal
authors.initials: P
authors.lastname: Dumy
authors.forename: Martine
authors.initials: M
authors.lastname: Demeunynck
mesh_terms: 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
chemical_list: D000588:Amines; D000609:Aminoacridines; D006146:Guanidines