QSAR analysis of caffeoyl naphthalene sulfonamide derivatives as HIV-1 integrase inhibitors

Abstract

Human immunodeficiency virus type 1 (HIV-1) integrase is a potential target for anti-HIV therapy. It is an essential enzyme required for replication of the acquired immunodeficiency syndrome (AIDS) virus. Caffeoyl naphthalene sulfonamide derivatives act against HIV integrase and thus have the potential to become a part of an anti-HIV drug regimen. Although caffeoyl naphthalene sulfonamide derivatives have all the features required of good anti-HIV agents such as the presence of bis-catechol moieties, polyaromatic rings, and a central linker, they do SO 2 NH Ac 2 caffeoyl-NH AcO AcO O O H O H O A c 2 -caffeoyl caffeoyl Ac 2 caffeoyl = acetylated caffeoyl groupnot perform well as anti-HIV agents in cell-based assays, that is, they do not stop viral replication at nontoxic concentration. We carried out a quantitative structure-activity relationship (QSAR) study of caffeoyl naphthalene sulfonamide derivatives via the software WIN CAChe 6.1 and STATISTICA to improve its activity. QSAR reveals that if partition coefficient, connectivity index, and shape index of these molecules are altered, the activity is likely to increase. On the basis of the QSAR model, we designed a new series of compounds, calculated the activities, and found that they were more potent than the existing compounds.

Different supramolecular architectures mediated by different weak interactions in the crystals of three N-aryl-2,5-dimethoxybenzenesulfonamides

“…The sulfonamide linkage plays a vital role as a key constituent in a number of biologically active molecules. Up to now, sulfonamides have been known to exhibit a wide variety of biological activities, such as antibacterial (Subhakara Reddy et al, 2012; Himel et al, 1971), antifungal (Hanafy et al, 2007), anti-inflammatory ISSN 2053ISSN -2296 # 2017 International Union of Crystallography (Kuçukguzel et al, 2013), antitumor , anticancer (Mansour et al, 2011), anti-HIV (Sahu et al, 2007) and antitubercular activities (Vora & Mehta, 2012). In recent years, extensive research has been carried out on the synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety for different activities, and have been reported to be important pharmacophores (Mohan et al, 2013).…”

QSAR study on some arylsulfonamides as anti-HIV agents

“…QSAR studies have provided valuable insight in the design and development of HIV-PI (Gupta et al, 1998;Gayathri et al, 2001;Garg et al, 1999;Kurup et al, 2003). We have already reported a few QSAR studies on anti-HIV agents (Sahu et al, 2007;Ravichandran and agrawal, 2007). Continuing this effort, herein we describe QSAR studies of some arylsulfonamide derivatives as potential anti-HIV agents.…”

4-Bromo-N-(4-bromophenyl)benzenesulfonamide

“…They play a vital role as key constituents in a number of biologically active molecules being known to exhibit a wide variety of biological activities such as antibacterial (Subhakara Reddy et al, 2012), insecticidal (Himel et al, 1971), antifungal (Hanafy et al, 2007), antihepatitis (Yan-Fang et al, 2010), anti-inflamatory (Kü çü kgü zel et al, 2013), antitumor , anticancer (Al-Said et al, 2011), anti-HIV (Sahu et al, 2007) and antitubercular activities (Vora et al, 2012). In recent years, extensive research has been carried out on the synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety, and they have been reported to be important pharmacophores (Mohan et al, 2013).…”