SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP OF N-(3-OXO-1-THIA-4-AZASPIRO[4.5] DECAN-4-YL)CARBOXAMIDE INHIBITORS OF INFLUENZA VIRUS HEMAGGLUTININ MEDIATED FUSION


Goktas F. , VANDERLINDEN E., NAESENS L., Cesur Z. , Cesur N. , Tas P.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.190, sa.7, ss.1075-1087, 2015 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 190 Konu: 7
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1080/10426507.2014.965819
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Sayfa Sayıları: ss.1075-1087

Özet

We report on synthesis and the structure-activity relationship of carboxamide-derived inhibitors of the influenza virus fusion function of the viral hemagglutinin. The newly synthesized carboxamides have a backbone structure similar to reported fusion inhibitors, consisting of an aromatic ring system linked to a non-aromatic cyclic system via an amide bridge. Condensation of 2-hydroxybenzohydrazide, 5-chloro-2-hydroxybenzohydrazide or 3-hydroxynaphthalene-2-carbohydrazide, appropriate carbonyl compounds and sulfanyl acids yielded corresponding N-(3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)carboxamides, using a one-pot three-component cyclocondensation method. The compounds were characterized by IR, H-1-NMR,C-13-NMR, and elemental analysis. All compounds were evaluated for antiviral activity against influenza A (H1N1, H3N2) and influenza B viruses in MDCK cell cultures. The contributions of different substituents on the antiinfluenza effect were discussed.