Domino synthesis of functionalized 1,6-naphthyridines and their in vitro anti-inflammatory and anti-oxidant efficacies

Abstract

Bioactive 1, 6-naphthyridines were constructed through a one pot multicomponent method by reacting different ketones with malononitrile and pyrrolidine. In vitro anti-inflammatory and 1,1-diphenyl-2picrylhydrazyl (DPPH) scavenging activities for all the synthesized 1, 6-naphthyridines were further carried out. These results clearly show that compound 3e exhibited excellent anti-inflammatory activity with a percentage inhibition of 81.24±4.46 by membrane stabilization method and 77.85±0.46 by the albumin denaturation method at a concentration of 100 µg ml -1 , which is comparable to the standard Diclofenac. A noticeable DPPH scavenging activity of 82.08±1.81 % was also observed for the synthesized compounds when compared with the standard, Ascorbic acid..

Recent Developments on Five-Component Reactions

“…Malononitrile attacks 117 tri the ring closure to form intermediates 118 which then react with an amine to produ products 116 after aromatization. A similar process reported by the Thirumalai gr ing same components, but different molar ratio, gave similar products [70]. The bi evaluation results indicated that all the synthesized products possess in-vitro antimatory and antioxidant activities.…”

One pot multi‐component synthesis of functionalized spiropyridine and pyrido[2,3‐d]pyrimidine scaffolds and their potent in‐vitro anti‐inflammatory and anti‐oxidant investigations

“…In continuation, our previously reported work on synthesis of functionalized-1,6-naphthyridines from acyclic ketones (Lavanya, Thirumalai, Asharani, & Aravindan, 2015), we have reacted cyclic ketones with malononitrile and pyrrolidine in ethanol under the same reaction condition anticipating the formation of spiro-1,6-naphthyridines. However, detailed examination of the product inferred that the formed product is fused spiropyridine (4a); and not spiro-1,6-naphthyridines (Scheme 1).…”

Synthesis of 1,6‐Naphthyridine and Its Derivatives: A Systematic Review

“…). [75] The obtained products yield varied from moderate to good (60-78 %). The aryl system with an electrondonating group afforded the product in good yields compared to the aryl system bearing the electron-withdrawing substituents.…”

“…The proposed mechanism is depicted in Figure 17. [75] The reaction between the carbonyl compound (234) and malononitrile (134) in the presence of pyrrolidine (235) afforded the knoevenagel condensation product (237). Another molecule of ketone served as Michael donor while reacting with α,βunsaturated compound (237).…”