21758-86-1Relevant academic research and scientific papers
Reaction of 2,3-dichloro-1,4-naphthoquinone with some active methylene compounds in different basic media
Hammam,Fandy,Hassan
, p. 400 - 405 (2002)
Reaction of 2,3-dichloro-1,4-naphthoquinone with some active methylene compounds, such as malononitrile and cyanoacetamide, under various basic conditions has been investigated. A mechanism for these reactions is proposed.
Synthesis of benzonaphthofuroquinones and benzoylnaphthindolizinediones by reactions of flavonoids with dichlone under basylous, oxygenous and aqueous conditions: Their cytotoxic and apoptotic activities
Chittiboyina, Amar G.,Haider, Saqlain,Khan, Shabana I.,Luo, Peng,Pan, Weigao,Wang, Mei,Wei, Wanxing
, p. 28644 - 28652 (2020)
Using flavonoids and dichlone as substrates, benzonaphthofuroquinones (1, 2, 3, 5, 6, novel; 4 new) and benzoylnaphthindolizinediones (7, 8, known; 9, new) were synthesized through common base-catalyzed method and a new method of combining base-catalyzed with O2/H2O exposing. The possible reaction mechanisms may involve the process like isomerization, hydration, oxidation, decomposition and intermolecular condensation. Benzonaphthofuroquinones (2, 3, 4, 5) were found to exhibit potent cytotoxicity against carcinoma cell lines and low toxicity to normal cell lines. The compounds 4 and 5 not only expressed a significant late-stage-apoptosis against human leukemia and melanoma, but also promoted the cleavage of caspase-3 and PARP in human leukemia, which suggested that the late-stage-apoptosis and caspase-3 pathway may be responsible for the cytotoxicities of these benzonaphthofuroquinones. The replacement of the furan ring with pyrrole system in benzoylnaphthindolizinediones (7, 8, 9) resulted in the loss of anticancer activity.
Heterocyclic Quinonoid Chromophoric Systems : Part V - Synthesis of 3,4-Phthaloyl-2-thiaquinolizine
Shah, J. N.,Tilak, B. D.
, p. 29 - 36 (2007/10/02)
Condensation of α-mercaptomethylpyridine with 1,4-naphthoquinone, 2-chloro-1,4-naphthoquinone and 2,3-dichloro-1,4-naphthoquinone leads to a number of quinonoid derivatives including the desired 2-α-pyridylmethylmercapto-1,4-naphthoquinone (XVI) and its 3-chloro derivative (XI).Cyclization of XVI and XI gives 3,4-phthaloyl-2-thiaquinolizine (I) which represents a new heterocyclic quinonoid chromophoric system.Plausible mechanisms for the formation of the different heterocyclic quinones are discussed.Interaction of 1,4-naphthoquinone with 1-mercaptomethylisoquinoline affords 8,9-benzo-3,4-phthaloyl-2-thiaquinolizine (XXI).The thiaquinolizines undergo sulphur extrusion on heating to m.p. or on treatment with alkaline dithionite to yield the corresponding 2,3-phthaloylpyrrocolines.
