59641-32-6Relevant academic research and scientific papers
Chemoselective reactions of 2,3-dichloro-1,4-naphthoquinone
Sarhan, Abd El-Wareth A. O.,Kamal El-Dean, Adel M.,Abdel-Monem, Maisa I.
, p. 205 - 212 (1998)
The reaction of 2,3-dichloro-1,4-naphthoquinone with alkoxides, primary amines, and phenols was shown to proceed chemoselectively rather to the corresponding 2-substituted 3-chloro-naphthoquinones or 2,3-disubstituted quinones than to brazanquinone deriva
Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON)
Varricchio, Carmine,Beirne, Kathy,Aeschlimann, Pascale,Heard, Charles,Rozanowska, Malgorzata,Votruba, Marcela,Brancale, Andrea
, p. 13638 - 13655 (2020/11/30)
Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 ?000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5′-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.
Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones
Santos, Maria M.M.,Faria, Natalia,Iley, Jim,Coles, Simon J.,Hursthouse, Michael B.,Martins, M. Luz,Moreira, Rui
experimental part, p. 193 - 195 (2010/04/05)
We report here a simple entry into naphtho[2,3-d]isoxazole-4,9-dione system containing a EWG in position 3 using the readily available 2,3-dichloro-1,4-naphthoquinone and nitromethyl derivatives in the presence of base. Antifungal activity of synthesised naphthoquinones was evaluated against ATCC and PYCC reference strains of Candida. The results suggest that the naphtho[2,3-d]isoxazole-4,9-dione scaffold has the potential to be developed into novel and safe therapeutic antifungal agents.
Synthesis and spectral properties of novel thionaphtoquinone dyes
Sayil, Cigdem,Ibis, Cemil
experimental part, p. 1233 - 1236 (2010/09/10)
2,3-Dichloro-1,4-naphtoquinone 1 compound was reacted with octadecanethiol 2 in two different mole ratio. Compound 3 was obtained from the reaction of 1 and 2 in 1:2 mole/mole ratio. Compounds 7 and 8 were obtained from reaction of 1 and 2 in 1:1 mole/mol
Synthesis and antiplatelet, antiinflammatory and antiallergic activities of 2,3-disubstituted 1,4-naphthoquinones
Lien, Jin-Cherng,Huang, Li-Jiau,Wang, Jih-Pyang,Teng, Che-Ming,Lee, Kuo-Hsiung,Kuo, Sheng-Chu
, p. 1181 - 1187 (2007/10/03)
Modification of 2-acetamido-3-chloro-1,4-naphthoquinone, which has potent antiplatelet, antiallergic and antiinflammatory activities, led to a series of 2,3-disubstituted 1,4-naphthoquinones. Some of these compounds showed significant antiplatelet, antiallergic and antiinflammatory activities. Among them, 2-methoxy-3-chloro-1,4-naphthoquinone (15) and 2- ethoxy-3-chloro-1,4-naphthoquinone (17) exhibited potent inhibitory effects on neutrophil and mast cell degranulation. 2-Methoxy-1,4-naphthoquinone (20) and 2-ethoxy-1,4-naphthoquinone (21) exhibited potent inhibitory effect on neutrophil superoxide formation. These four compounds were thus selected for further evaluation.
Substituted 1,4-Naphthoquinones vs. the Ascitic Sarcoma 180 of Mice
Hodnett, Ernest M.,Wongwiechintana, Chinda,Dunn, William J.,Marrs, Pam
, p. 570 - 574 (2007/10/02)
Twelve 1,4-naphthoquinones have been tested against the ascitic form of sarcoma 180 in Swiss mice.Statistical analysis shows that the most important molecular parameter determining their effectiveness in prolonging the life of mice bearing this tumor is their redox potentials.Although the toxicities of the compounds are also related to the redox potentials in the same way, the therapeutic indexes can be increased by adding substituents of greater lipophilicity.The naphthoquinones differ greatly in antitumor activities and may inhibit the growth of malignant cells by different mechanisms
