2-substituted indazoles. Synthesis and antimicrobial activity

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

2-Isothiocarbamoyl substituted fused pyrazolines and their S-alkyl derivatives were prepared as potentially antimicrobial agents. Conventional methods were used to synthesize the novel derivatives starting from cyclic unsaturated ketones and thiosemicarbazide under acidic catalyst. These cyclizations yielded only one diastereoisomer of 3-H, 3a-H cis. The alkylations were performed applying alkyl halides. The structures of the new compounds, including configurations and conformations, were elucidated by NMR spectroscopy, also making use of 2D-HSC, DEPT and DNOE measurements. The S- alkyl derivatives were evaluated for activity against Gram-negative and Gram- positive bacteria and their in vitro toxicity was determined on HeLa cells. The structure-activity relationship was also studied.

Original languageEnglish
Pages (from-to)1009-1018
Number of pages10
JournalEuropean Journal of Medicinal Chemistry
Volume34
Issue number11
DOIs
Publication statusPublished - Nov 1999

Fingerprint

Indazoles
Alkylation
Gram-Positive Bacteria
Cyclization
Structure-Activity Relationship
Anti-Infective Agents
Ketones
HeLa Cells
Magnetic Resonance Spectroscopy
Derivatives
Nuclear magnetic resonance spectroscopy
Toxicity
Conformations
Bacteria
Catalysts
In Vitro Techniques
thiosemicarbazide

Keywords

  • Alkylation
  • Antibacterial effect
  • In vitro toxicity
  • Indazole
  • Stereostructure by NMR

ASJC Scopus subject areas

  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

2-substituted indazoles. Synthesis and antimicrobial activity. / Lóránd, T.; Kocsis, Béla; Emődy, L.; Sohár, P.

In: European Journal of Medicinal Chemistry, Vol. 34, No. 11, 11.1999, p. 1009-1018.

Research output: Contribution to journalArticle

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