A Greener Approach Synthesis and Docking Studies of Perimidine Derivatives as Potential Anticancer Agents

Abstract

Microwave solvent‐free technique was employed to the synthesis of series of 2‐(1H‐perimidin‐2(3H)‐ylidene) derivatives, 4‐(1H‐perimidin‐2‐yl)‐1H‐pyrazole‐3‐carboxamides, pyrrolo[1,2‐a]perimidin‐10‐ones, and 8H‐[1,2,4]triazolo[4,3‐a]perimidine. Compared with conventional method, the obvious feature of microwave method is higher in chemical yield, faster reaction rate, and cleaner reaction condition. The structures of the synthesized compounds were confirmed based on their elemental analyses and spectroscopic data (FT‐IR, 1H‐NMR, 19F‐NMR, 13C‐NMR, and LC‐MS/MS). Some of the synthesized compounds exhibit anticancer potential against the growth of both the human breast (MCF‐7) and the liver carcinoma (HepG2) tumor cells. The most active cytotoxic perimidine derivatives were docked against topoisomerase II to investigate their binding and DNA intercalating activity against the protein crystal structure.

Recent Advances in the Synthesis of Perimidines and their Applications

“…Eldeab and colleagues [ 136 ] synthesized a variety of perimidine conjugates and evaluated their cytotoxicity against liver carcinoma (HepG2) and human breast (MCF-7) cancer cell lines. 2-(1 H -perimidin-2-(3 H )-ylidene) derivatives were synthesized by the reaction of naphthalene-1,8-diamine and β-keto esters with potassium carbonate under microwave irradiation (MWI).…”

Metal Free Sulfonic Acid Functionalized Carbon Catalyst for Green and Mechanochemical Synthesis of Perimidines

“…In particular, perimidine moiety is an important nitrogen-containing heterocycle in the context of pharmaceutical, natural products, chemo-sensors, and functional materials [1] . Perimidines play a significant role in various biological activities like anti-cancer, anti-lipase, anti-microbial, anti-oxidant and anti-inflammatory and so on [2][3][4][5][6][7] [ Figure 1]. Furthermore, it works as an intermediate, catalyst precursor, photochemical sensor, stopper for supramolecules, and display DNAbinding properties [8][9][10][11][12] .…”

Design, Synthesis and Cytotoxic Activities of Pyrazole‐Perimidine Hybrids

“…[11] There are many studies on the biological activities of perimidines and its chemical applications. And also, various substituted perimidines show antibacterial, [12] antiinflammatory, [13] antifungal, [14] antitumor, [15] anticancer, [16] acetylcholinesterase inhibitor [17] and cytotoxic effect. [18] Some perimidine compounds exhibiting biological activity and fluorescence properties are given in the Figure 1.…”