Synthesis and In Vitro Evaluation of the Anti-Viral Activity of N-[4-(1H(2H)-benzotriazol-1(2)-yl)phenyl]alkylcarboxamides

Title: Synthesis and In Vitro Evaluation of the Anti-Viral Activity of N-[4-(1H(2H)-benzotriazol-1(2)-yl)phenyl]alkylcarboxamides

Volume: 2 Issue: 6

Author(s): Antonio Carta, Giovanni Loriga, Sandra Piras, Giuseppe Paglietti, Marco Ferrone, Maurizio Fermeglia, Sabrina Pricl, Paolo La Colla, Barbara Secci, Gabriella Collu and Roberta Loddo

Affiliation:

Keywords: Benzotriazolylphenylcarboxamides, Anti-viral activity, Picornaviridae, Cytotoxicity, SAR, Polio virus (Sb-1)helicase, in silico evaluation

Abstract: A series N-[4-(1H(2H)-benzotriazol-1(2)-yl)phenyl]alkylcarboxamides (8e-k, 9e-i, k, l) and their parent amines (5a-c and 6a-d) were prepared according to Schemes (1 and 2). Compounds were evaluated in vitro for cytotoxicity and antiviral activity against a wide spectrum of RNA (positive- and negative-sense) viruses, like [Bovine Viral Diarrhea Virus (BVDV), Yellow Fever Virus (YFV), Coxsackie Virus B (CVB-2), Polio Virus (Sb-1), Human Immunodeficiency Virus (HIV-1), Respiratory Syncytial Virus (RSV)] or double-stranded (dsRNA) virus, like Reoviridae (Reo-1). The Entero (CVB-2 and Sb-1) were the only viruses inhibited by title compounds. In particular, two of them emerged for their selective, although not very potent, antiviral activity: 8i, which was the most active against CVB-2 (CC50 > 100 M; EC50 = 10μ M) and 9l, which was the most active against Sb-1 (CC50 90μM; EC50 = 30μm). Title compounds were evaluated in silico against the Sb-1 helicase, as the crystal structure of this enzyme was not available, the corresponding 3D model was obtained by homology techniques (see Fig. 2).

Cite this article as:

Carta Antonio, Loriga Giovanni, Piras Sandra, Paglietti Giuseppe, Ferrone Marco, Fermeglia Maurizio, Pricl Sabrina, La Colla Paolo, Secci Barbara, Collu Gabriella and Loddo Roberta, Synthesis and In Vitro Evaluation of the Anti-Viral Activity of N-[4-(1H(2H)-benzotriazol-1(2)-yl)phenyl]alkylcarboxamides, Medicinal Chemistry 2006; 2 (6) . https://dx.doi.org/10.2174/1573406410602060577