Cationic porphyrin–quinoxaline conjugate as a photochemically triggered novel cytotoxic agent

A Convenient Way to Quinoxaline Derivatives through the Reaction of 2-(3-Oxoindolin-2-yl)-2-phenylacetonitriles with Benzene-1,2-diamines

“…Many quinoxaline-based natural products have shown a broad range of bioactivities [ 6 , 7 ] and naturally, this heterocyclic core is considered one of the privileged pharmacophoric scaffolds for drug design [ 8 ]. In some cases, those compounds were successfully employed as efficient fluorescent probes used in molecular electronics, analytical chemistry, and the design of photo-triggered medicines [ 9 , 10 , 11 ] while quinoxalines 4 bearing ortho-aniline moiety at C-2 (or their closely related derivatives) has attracted great attention as selective DNA triple- and quadruple-helix intercalating ligands [ 12 , 13 , 14 , 15 , 16 , 17 ]. Nowadays, many synthetic approaches to these structures have been developed, although most of them rely on multi-step functional group transformation sequences.…”

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

“…Hybrid 14 displayed an IC 50 value of 0.06 mM (under a white LED light source, k ¼ 400-800 nm, 2 mW and irradiation for 10 min.) against the A549 cancer cell line, showing 5-fold better inhibitory activity than the reference compound 15 (H 2 TMPyP, IC 50 ¼ 0.30 mM) 34 . Jelovica et al 35 designed and synthesised an amphiphilic porphyrin derivative with a long lipophilic alkyl side chain.…”

Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine

“…In addition, fluoroquinoxaline 89 was reported to have remarkable anticancer activities [100a,b], while the N-alkylated quinoxalinone 90, was suggested to act as a potent cancer chemopreventive agent [101]. Porphyrin bearing quinoxaline 91 displayed enhanced photocytotoxicity (IC 50 = 0.06 µM) when compared to TMPyP against A549 cancer cells [102]. Various authors have also reported the potential utilization of quinoxaline pharmacophores 92 [103], 93 [104], 94 [105], 95 [105], 96 [106] and 97 [107] as anticancer agents of choice.…”