ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Fluorescence and Structure of Methylated Acridin-9-ylthioureas

P. Kristian, E. Balentová, J. Bernát, J. Imrich, E. Sedlák, I. Danihel, S. Böhm, N. Prónayová, K. D. Klika, K. Pihlaja, and J. Baranová

Institute of Chemistry, Faculty of Natural Sciences, P. J. Šafárik University, SK-041 67 Košice

E-mail: bernat@kosice.upjs.sk

Received: 28 February 2003

Abstract: Fluorescence and structure of acridin-9-ylthioureas with primary amino rest and their Smethylated products have been studied. The synthesized 1-(acridin-9-yl)-3-alkyl-S-methylisothiuronium iodides exhibit about one order increased fluorescence in comparison with corresponding thioureas. The structure of products obtained by methylation reactions was confirmed by NMR techniques including PDQF-COSY, selective INEPT, NOE difference experiments, and quantumchemical calculations (AM1, ab initio). A free rotation of 9-substituents in relation to acridine skeleton has been found. The conformers of acridinylisothioureas are in E-configuration relative to the C==N bond with more favourable imino (C-9==N) tautomeric structure.

Full paper in Portable Document Format: 584a268.pdf

Chemical Papers 58 (4) 268–275 (2004)