Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives

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Atıf İçin Kopyala

Cihan-Ustundag G., NAESENS L., Satana D., Erkose-Genc G., Mataraci-Kara E., Capan G.

MONATSHEFTE FUR CHEMIE, cilt.150, sa.8, ss.1533-1544, 2019 (SCI-Expanded)

• Yayın Türü: Makale / Tam Makale
• Cilt numarası: 150 Sayı: 8
• Basım Tarihi: 2019
• Doi Numarası: 10.1007/s00706-019-02457-9
• Dergi Adı: MONATSHEFTE FUR CHEMIE
• Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Sayfa Sayıları: ss.1533-1544
• Anahtar Kelimeler: Heterocycles, Spirothiazolidinone, Antitubercular activity, Antiviral activity, Cytotoxicity, Drug research, MYCOBACTERIUM-TUBERCULOSIS, BIOLOGICAL EVALUATION, RAPID DETECTION, INDOLE-2-CARBOXAMIDES, INHIBITORS, DRUGS, ANTIMYCOBACTERIAL, RESISTANCE, THERAPIES, REGIMENS
• İstanbul Üniversitesi Adresli: Evet

Özet

A series of indole-based spirothiazolidinones have been designed, synthesized and evaluated, in vitro, for their antitubercular, antiviral, antibacterial, and antifungal activities. The structures of the new compounds were established by IR, H-1 NMR, C-13 NMR (proton decoupled, APT, and DEPT), electrospray ionization mass spectrometry, and microanalysis. Compounds bearing a phenyl substituent at position 8 of the spiro ring, exhibited significant antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 at concentrations of 3.9 and 7.8 mu M. Still, some of the tested compounds displayed activity on mycobacteria with MIC values of 16 and 31 mu M. Four of the indole-spirothiazolidinone derivatives were found to be moderately active against Punta Toro virus, yellow fever virus or Sindbis virus in Vero cells. The antiviral EC50 values were in the range of 1.9-12 mu M and the selectivity index (ratio of cytotoxic to antivirally effective concentration) was above 10 in some cases. The most potent effect was seen with the compound that is methylated at positions 2 and 8 of the spirothiazolidinone system.