New 5-methylisatin including thiocarbohydrazones: preparation, structure elucidation and antimicrobial activity


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Yakan H., Çakmak Ş., Buruk O., Veyisoğlu A., Muğlu H., Türköz Karakullukçu N.

RESEARCH ON CHEMICAL INTERMEDIATES, cilt.48, sa.10, ss.4331-4345, 2022 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 48 Sayı: 10
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1007/s11164-022-04799-2
  • Dergi Adı: RESEARCH ON CHEMICAL INTERMEDIATES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, Environment Index, Index Chemicus (IC)
  • Sayfa Sayıları: ss.4331-4345
  • Anahtar Kelimeler: Isatin, Thiocarbohydrazones, Schiff bases, Antimicrobial activity, Spectroscopic studies, Minimum inhibitory concentration (MIC), BIS-ISATIN CARBOHYDRAZONE, ANTIVIRAL ACTIVITY, SCHIFF-BASES, ANTIOXIDANT ACTIVITIES, MOLECULAR DOCKING, MANNICH-BASES, ANTIBACTERIAL, DERIVATIVES, ANTIFUNGAL, DESIGN
  • Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

New 5-methylisatin including thiocarbohydrazones (1-5) have been synthesized. The chemical structure of synthesized compounds was elucidated with IR, H-1 NMR, C-13 NMR spectroscopic methods, and elemental analysis. Moreover, the synthesized compounds have been screened for antimicrobial activity. Their antibacterial activities were tested against Gram-positive (Bacillus subtilis ATCC 6623, Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212), Gram-negative (Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 70060, Pseudomonas aeruginosa ATCC 27853), and fungal (Candida albicans ATCC 10231, Aspergillus niger ATCC 16404) microbial strains using the microdilution method. In the isatin series, particularly the compound 2 showed the best antimicrobial activity against E. faecalis strain with MIC values of 64 mu g/mL compared to other compounds. This high activity of compound 2 is due to the presence of two electron-donating methoxy groups in its structure. The remaining substituted compounds have shown good and moderate antimicrobial activity compared to standard drugs. The results may provide insights into the target compounds' structure-activity relationships, which may facilitate the development of pharmacological and biological applications for the target compounds.