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 pKa detn. show that the presence of the strongly basic guanidine has a dramatic influence on the ionization of the acridine nucleus by lowering the pKa value down to 4.49. [on SciFinder(R)]
Références
- Titre
- Synthesis of N-acridinyl-N'-alkylguanidines: Dramatic influence of amine to guanidine replacement on the physicochemical properties.
- Type de publication
- Article de revue
- Année de publication
- 2008
- Auteurs
- Zeghida, Walid, Debray Julien, Michel Carine, Milet Anne, Dumy Pascal, and Demeunynck Martine
- Revue
- Bioorg. Med. Chem. Lett.
- Volume
- 18
- Pagination
- 4779–4782
- ISSN
- 0960-894X
- Mots-clés
- acridinylalkylguanidine prepn basicity
Soumis le 12 avril 2018