Synthesis and Evaluation of Novel 4-Substituted Styryl Quinazolines as Potential Antimicrobial Agents

• Published in: Archiv der Pharmazie (Weinheim) 2012-12, Vol.345 (12), p.964-972
• Main Authors: Modh, Rahul P., Patel, Amit C., Mahajan, Dharmesh H., Pannecouque, Christophe, De Clercq, Erik, Chikhalia, Kishor H.
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Anti-HIV; Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - chemistry; Anti-HIV Agents - pharmacology; Antibacterial; Aryl thiourea; Aryl urea; Gram-Negative Bacteria - drug effects; Gram-Negative Bacteria - growth & development; Gram-Positive Bacteria - drug effects; Gram-Positive Bacteria - growth & development; HIV; HIV-1 - drug effects; HIV-1 - physiology; HIV-2 - drug effects; HIV-2 - physiology; Human immunodeficiency virus; Microbial Sensitivity Tests; Molecular Structure; Quinazoline; Quinazolines - chemical synthesis; Quinazolines - chemistry; Quinazolines - pharmacology; Styryl; Virus Replication - drug effects
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/ardp.201200291

In an attempt to afford possible antibacterial and anti‐human immunodeficiency virus (HIV) agents, a series of 22 novel styryl quinazoline‐based heterocyclic entities were designed and synthesized. Various substituted aryl urea and thiourea cores were incorporated at position 4 of quinazoline, followed by styrylation of position 2, aiming at an augmented biological potential. The synthesized compounds were well characterized through IR, 1H NMR, 13C NMR and elemental analyses. All compounds were screened for their in vitro anti‐HIV activity against the HIV‐1 (IIIB) and HIV‐2 (ROD) strains. The antibacterial activity was also evaluated against various pathogenic Gram‐positive and Gram‐negative bacterial strains. A series of 22 novel styryl quinazoline‐based heterocyclic entities were designed and synthesized to afford possible antibacterial and anti‐human immunodeficiency virus (HIV) agents. All of the prepared compounds were screened for their in vitro anti‐HIV activity against the HIV‐1 (IIIB) and HIV‐2 (ROD) strains. The antibacterial activity was also evaluated against various pathogenic Gram‐positive and Gram‐negative bacterial strains.