Naphthoquinones and derivatives as potential anticancer agents: An updated review

A new class of anti-proliferative activity and apoptotic inducer with molecular docking studies for a novel of 1,3-dithiolo[4,5-b]quinoxaline derivatives hybrid with a sulfonamide moiety

“…Our study was extended to include synthesizing novel [1,3] dithiolo [4,5-b]quinoxaline linked to cyclohexyl, pyrazolyl, and pyrimidinyl moieties. Thus, the reaction of the dithioate salts derived from cyclic active methylene compounds 11, 13, 15, and 17 with compound 7 in N,N-dimethylformamide at room temperature gave the corresponding [1,3] The analytical and spectral data of compounds 12, 14, 16, and 18 were in agreement with their proposed structure. Thus, the 1 H NMR spectrum of compound 14 showed a quintet at d 1.69 ppm assigned to methylene protons (C 3 and C 4 ) of the pyrrolidine ring, a triplet at d 3.27 ppm assigned to methylene protons (C 2 and C 5 ) of the pyrrolidine ring, and a singlet at d 2.39 ppm assigned to methyl protons at position-4 of the pyrazole ring.…”

“…As viewed in Scheme 2, the treatment of 2,3-dichloro-6-(pyrrolidin-1-ylsulfonyl) quinoxaline 7 with potassium ethene-1,1-bis-(thiolates) 9 at room temperature in N,N-dimethylformamide A proposed mechanism for forming 2-ylidene-[1,3]dithiolo [4,5-b]quinoxalines 10a-f is described in Scheme 3. The formation of [1,3]dithiolo [4,5-b]quinoxalines 10a-f are assumed to proceed via nucleophilic addition of ethene-1,1-dithiolates anion 9 to the activated double bond at position-3 in 2,3dichloro-6-(pyrrolidin-1-ylsulfonyl)quinoxaline 7 to give the non-isolable intermediate A and B, followed by intramolecular cyclization by elimination of potassium chloride to afford the nal product 10, Scheme 3. The structures of [1,3]dithiolo [4,5-b] quinoxalines 10a-f have been further conrmed from independent work via a one-pot, three-component, reaction of active methylene compounds with carbon disulde in the presence of a base, followed by in situ coupling of the resulting dithioate salts with 2,3-dichloro-6-(pyrrolidin-1-ylsulfonyl) quinoxaline 7 to afford a product identical in all respect (m.p., mixed M.p., TLC, and spectra).…”

“…1 The greatest cause of mortality worldwide is cancer, which claims 1.61 million lives annually (19.41%) including 0.79 million from liver cancer (9.2%), and 0.79 million from stomach cancer (9.2%). 2,3 In addition, breast cancer is the most commonly diagnosed cancer in women, with 287 000 women expected to receive a diagnosis by 2022. 4 Despite early detection and treatment advances, patients with distant metastases of breast cancer oen get poor results due to their low incomes and the high cost of therapies.…”

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A new series of 6-(pyrrolidin-1-ylsulfonyl)- [1,3]dithiolo [4,5-b]quinoxaline-2-ylidines 10a-f, 12, 14, 16, and 18 were designed, synthesized, and evaluated for their in vitro anticancer activity. The structures of the novel compounds were systematically characterized by 1 H NMR, 13 C NMR, and elemental analysis.

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The Effects of 1,4-Naphthoquinone (NQ) and Naphthazarin (5,8-Dihydroxy-1,4-naphthoquinone, DHNQ) Individually and in Combination on Growth and Oxidative Stress in Maize (Zea mays L.) Seedlings

“…Naphthoquinones are the products of bacterial and fungal metabolism, as well as secondary metabolism in higher plants, where they are produced and used as natural defense chemicals [ 1 , 2 , 3 , 4 ]. Naturally occurring naphthoquinones, such as juglone (5-hydroxy-1,4-naphthoquinone), lawsone (2-hydroxy-1,4-naphthoquinone), plumbagin (2-methyl-5-hydroxy-1,4-naphthoquinone), naphthazarin (5,8-dihydroxy-1,4-naphthoquinone), and others, have been studied for a long time due to their importance in medicinal and biological research [ 5 , 6 , 7 , 8 , 9 ], and recently in the energy and chemical industries [ 10 , 11 , 12 ]. Interestingly, in the last two cases, naphthoquinone can be used as an organic component of the positive electrode in an ecological battery or as a natural corrosion inhibitor.…”