Synthesis of novel potent cytotoxicy podophyllotoxin-naphthoquinone compounds via microwave-assited multicomponent domino reactions

A Green and Efficient NH4OAc-catalyzed Synthesis of 2-Hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones

“…Several lead 1,4-naphthoquinone compounds are lawsone, α-lapachone and bostrycoidin). The synthesis of bioactive 1,4-naphthoquinone derivatives based on multicomponent domino reactions is currently one of major research strategies of our group [3][4][5][6][7].…”

Microwave‐Assisted Three‐Component Synthesis of Novel N‐Arylated‐Dihydrobenzo[g]quinoline‐5,10‐Diones and Their Potential Cytotoxic Activity

“…[15,16] The synthesis of this privileged structure has, therefore, attracted the significant interest of chemists. [17][18][19][20][21][22][23][24][25][26][27][28][29][30] The classical synthetic routes of several 1-aza-anthraquinones have usually involved a hetero-Diels-Alder reaction between an azadiene and naphthoquinone, [17,18] a cycloisomerization of Npropargylaminoquinone, [19][20][21] the Friedel-Crafts approach, [22] radical couplings using 2-amino-1,4naphthoquinones. [23][24][25] Recently, metal-free, one-pot reactions of 3-formylchromones and 2-aminonaphthalene-1,4-dione have been developed to afford 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives.…”

“… [12–14] Aza‐anthraquinones such as pixantrone ( Figure 1) have also known as anti‐cancer chemotherapeutic agents that interact with DNA through intercalation [15,16] . The synthesis of this privileged structure has, therefore, attracted the significant interest of chemists [17–30] . The classical synthetic routes of several 1‐aza‐anthraquinones have usually involved a hetero‐Diels‐Alder reaction between an azadiene and naphthoquinone, [17,18] a cycloisomerization of N ‐propargylaminoquinone, [19–21] the Friedel‐Crafts approach, [22] radical couplings using 2‐amino‐1,4‐naphthoquinones [23–25] .…”

“…In recent years, dihydrobenzo[ g ]quinoline‐5,10‐diones, which are crucial analogs of 1‐aza‐anthraquinone, have been widely studied and reported for remarkable biological activities [28–30] . A number of literature methods for the synthesis of 1,4‐dihydrobenzo[ g ]quinoline‐5,10‐diones, has been developed using multicomponent reactions, [28,31–33] however there are not many researches about N ‐arylated‐dihydrobenzo[ g ]quinoline‐5,10‐diones as well as their synthetic routes.…”

4-(Dimethylamino)pyridine as an Efficient Catalyst for One-Pot Synthesis of 1,4-Pyranonaphthoquinone Derivatives viaMicrowave-Assisted Sequential Three Component Reaction in Green Solvent

“…32 To the best of our knowledge, there has been no study of the synthesis of 1,4-pyranonaphthoquinone derivatives using DMAP as a catalyst so far. Thus, in continuation of our interests in the synthesis of naphthoquinone derivatives [33][34][35][36][37][38] and multicomponent reactions, [35][36][37][38] herein, we report the synthesis of 1,4-pyranonaphthoquinone derivatives bearing amino and cyano groups via a microwave-assisted three-component reaction between 1,4-naphthoquinone, malononitrile and arylaldehydes using DMAP as an efficient catalyst in ethanol, an environmentally preferable solvent. Besides that, with the aim to discover potent antimicrobial and antifungal agents, the antimicrobial and antifungal activities of the synthetic compounds were evaluated against Gram-positive and Gram-negative bacteri, and fungal strains.…”