Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives

Abstract

In the present article, we describe the synthesis, anti-HIV1 profile and molecular modeling evaluation of 11 oxoquinoline derivatives. The structure-activity relationship analysis revealed some stereoelectronic properties such as LUMO energy, dipole moment, number of rotatable bonds, and of hydrogen bond donors and acceptors correlated with the potency of compounds. We also describe the importance of substituents R(2) and R(3) for their biological activity. Compound 2j was identified as a lead compound for future investigation due to its: (i) high activity against HIV-1, (ii) low cytotoxicity in PBMC, (iii) low toxic risks based on in silico evaluation, (iv) a good theoretical oral bioavailability according to Lipinski 'rule of five', (v) higher druglikeness and drug-score values than current antivirals AZT and efavirenz.

Photoinduced Superoxide Radical Anion and Singlet Oxygen Generation in the Presence of Novel Selenadiazoloquinolones (An EPR Study)

“…In selenadiazoloquinolone solutions, equilibrium between oxo‐ or hydroxy‐tautomeric forms may be established, with tautomer concentrations significantly affected by solvent polarity, as well as by the structure of the substituent at the ortho position to the oxo group (43–46).…”

“…*Corresponding author email: vlasta.brezova@stuba.sk (Vlasta Brezova´) Ó 2010 The Authors Photochemistry and Photobiology Ó 2010 The American Society of Photobiology 0031-8655 /11 Photochemistry and Photobiology, 2011, 87: [32][33][34][35][36][37][38][39][40][41][42][43][44]…”

Copper(II) complexes with new fluoroquinolones: Synthesis, structure, spectroscopic and theoretical study, DNA damage, cytotoxicity and antiviral activity

“…The biological impact of fluoroquinolones (FQs) is characterized besides the broad antibacterial activity [1][2][3][4] also by anti-HIV [5][6][7] or antimycobacterial [7][8][9][10] effects. The action of fluoroquinolones is based on the inhibition of two enzymes involved in bacterial DNA synthesis, that are essential for bacterial DNA replication both of which are DNA topoisomerases that human cells lack.…”

Original Article. Study of the cytotoxic/toxic potential of the novel anticancer selenodiazoloquinolone on fibroblast cells and 3D skin model

“…Quinolone derivatives are multitarget agents with a variety of biological activities (Sharma et al ., 2009; Chung et al ., 2010; Darque et al ., 2009; Santos et al ., 2009; Sokolova et al ., 2009; Meyer et al ., 2007; Vinayaka et al ., 2014; Huang et al ., 1998; Oriel, 1998). Quinolones were shown to possess also antitumor and immunomodulatory activities (Tawfik et al ., 1990; Xia et al ., 2001; Riesbeck, 2002; Dalhoff & Shalit, 2003; Dalhoff, 2005; Drygin et al ., 2009; You et al ., 2009; Chou et al ., 2009; Azema et al ., 2009; George & Pilli, 2013).…”