Environmentally Benign Copper Triflate‐Mediated Multicomponent One‐Pot Synthesis of Novel Benzo[g]chromenes Possess Potent Anticancer Activity

Abstract

An efficient multi‐component one‐pot synthesis of highly functionalized 5,10‐dihydro‐4H‐benzo[g]chromenes‐3‐caronitrile derivatives from 2‐hydroxy‐1,4‐naphthoquinone, aromatic aldehyde and malonitrile in the presence of Cu(OTf)2 catalyst and eco friendly polyethylene glycol solvent was carried out under ultrasonication. The reaction was completed within 10 minutes and resulted in good yield. The synthesized compounds were tested for their in‐vitro anticancer activity against cervical cancer cell line (HeLa). Nine out of ten compounds showed potent antitumor activity better than that of doxorubicin. 2‐Amino‐4‐(3‐methoxy‐2‐hydroxy)‐5,10‐dioxo‐5,10‐dihydro‐4H‐benzo[g]chromene‐3‐carbonitrile displayed highest activity among the test compounds and doxorubicin with IC50 equal to 1.27 μM.

An Efficient One‐Pot Pseudo Five‐Component Synthesis of Bis‐heteroarylaminomethylnaphthoquinone Mannich Bases from Lawsone

“…In all the cases, the products were purified in boiling ethanol avoiding the conventional chromatographic separation. The structures of the new synthesized compounds 4were characterized by IR, 1 H-NMR, 13 C-NMR, MS analysis, and melting points.…”

“…Moreover, synthetic bioactive naphthoquinones containing the lawsone fragment have shown biological activities, examples of which are illustrated in Figure 1 [10] . However, the chemical modification of lawsone such as introducing nitrogen atom in lawsone enhances its biological activity [11–14] . One of the strategies for introducing nitrogen atom in lawsone is the formation of its Mannich base via Mannich reaction.…”

“…[10] However, the chemical modification of lawsone such as introducing nitrogen atom in lawsone enhances its biological activity. [11][12][13][14] One of the strategies for introducing nitrogen atom in lawsone is the formation of its Mannich base via Mannich reaction. Aminomethylnaphthoquinone Mannich bases derived from lawsone and their metal complexes belong to an important class of organic/ organometallic compounds have demonstrated a series of important biological properties such as antibacterial, [15] antiviral, [16] antimalarial, [17] cholinesterase inhibitors, [18] anticancer, [19] antifungal, [20] antimolluscicidal, [21] leishmanicidal, [22] anti parasitic [23] activities and they have also been employed as fluorescent compounds and dyes.…”

Copper‐Catalysed Multicomponent Syntheses of Heterocycles

“…An efficient environmentally benign one pot Cu(OTf) 2 catalysed multicomponent reaction for the synthesis of novel benzo[ g ]chromenes which possess potent anticancer activity was reported for the first time . The reaction involves 2‐hydroxy‐1,4‐naphthoquinone, malononitrile and aromatic aldehyde as reactants and carried out in the presence of Cu(OTf) 2 catalyst and green polyethylene glycol solvent under ultrasonication.…”

CeO2/CuO@N‐GQDs@NH2 nanocomposite as a high‐performance catalyst for the synthesis of benzo[g]chromenes

“…Therefore, searching for efficient methods for the preparation of chromenes is an attractive challenge. A number of methods have been developed for the preparation of chromenes using diverse catalysts containing lipase, [ 8 ] p ‐TSA, [ 9 ] Et 3 N, [ 10 ] Zn[ l ‐proline] 2 , [ 11 ] [Et 3 NH][HSO 4 ], [ 12 ] DBU, [ 13 ] Cu (OTf) 2 , [ 14 ] TEBA (triethylbenzylammonium chloride) [ 15 ] and [bmim]OH. [ 16 ] Metal oxides are a broad class of materials that have been researched extensively owing to their unique attributes and potential applications in various fields.…”