Schiff bases of methanesulfonylhydrazine. Synthesis, spectroscopic characterization, conformational analysis, and biological activity


Dodoff N., Ozdemir Ü., Karacan N., Georgieva M., Konstantinov S., Stefanova M.

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, vol.54, no.12, pp.1553-1562, 1999 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 54 Issue: 12
  • Publication Date: 1999
  • Doi Number: 10.1515/znb-1999-1213
  • Journal Name: ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1553-1562
  • Keywords: Schiff bases, methanesulfonylhydrazine, H-1 NMR data, molecular mechanics, cytotoxic activity, SALICYLALDIMINE COMPLEXES, VIBRATIONAL FREQUENCIES, PMR SPECTRA, RESISTANCE, PATTERNS, LIGANDS
  • Gazi University Affiliated: Yes

Abstract

Three novel Schiff bases: salicylaldehyde methanesulfonylhydrazone (1), 2-hydroxyacetophenone methanesulfonylhydrazone (2) and 2-hydroxy-1-naphthaldehyde methanesulfonylhydrazone (3) have been synthesized. Compounds 1-3, as well as acetone methanesulfonylhydrazone (4) have been characterized by TLC, H-1 NMR and IR spectra. The spectroscopic results for 1-3 have revealed the presence of an intramolecular hydrogen bond between the hydroxyl group and the imine N atom. The conformational isomerism of 1-4 with respect to the rotations around the SN and NN bonds have been studied by the method of molecular mechanics. Compounds 1-4 and methanesulfonylhydrazine exhibit antibacterial and cytotoxic effects.