In this article, we report a novel, rapid and facile synthesis of a series of azo coupled Ugi four-component reaction derivatives and its evaluation for biological activity. A general and straightforward approach towards the microwave-assisted synthesis was initiated by the condensation reaction to obtain compounds 5 (a-h) achieving 80-92% yields. The reactions were irradiated for 5-10 min in presence of fluorite catalyst. The resulting compounds were diazotized followed by coupling reaction to attain compounds 7 (a-h) with 65-74% yields. The synthesized compounds were characterized on the basis of 1H and 13C NMR, I.R, elemental analysis, and mass spectral data. All the synthesized derivatives 7 (a-h) were screened for their potential in vivo anti-inflammatory action against a reference drug, Diclofenac. These compounds were also screened for in vitro antimicrobial activity against a few Gram- positive and Gram-negative bacteria using reference antibiotics, Ampicillin and Streptomycin. The screening data revealed that compounds 7g and 7h possess potential anti-inflammatory activity while compounds 7a, 7b, 7g and 7h show potent antimicrobial activity. Structural variations bring about new physical and biological properties. As a result, azo coupled Ugi-4CR derivatives in near future can be used as potent drugs for inflammation and bacterial infections.
Anti-inflammatory, antimicrobial, azo dye, green synthesis, microwave, Ugi reaction
Department of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur, India.