6307-22-8Relevant academic research and scientific papers
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.
A simple synthesis of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B
Castro-Castillo, Vicente,Suárez-Rozas, Cristian,Simpson, Sebastián,Barriga-González, Andrés
, p. 553 - 559 (2017/08/30)
[Figure not available: see fulltext.] We followed a simple, inexpensive, and efficient route to synthesize a series of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B, with the expectation that this scaffold might exhibit antineoplastic activity. 5-Chlorobenzo[f]quinoxalin-6-ylacetate and 4-benzylbenzo[f]quinoxalin-6(4H)-one were obtained for the first time.
Dichloro-naphthoquinone as a non-classical inhibitor of the mycobacterial carbonic anhydrase Rv3588c
Dallaston,Rajan,Chekaiban,Wibowo,Cross,Coster,Davis,Hofmann
supporting information, p. 1318 - 1321 (2017/07/07)
The soluble mycobacterial carbonic anhydrases Rv3588c and Rv1284 belong to a different class of carbonic anhydrases than those found in humans, making them attractive drug targets by using the inherent differences in the folds of the different classes. By screening a natural product library, we identified naphthoquinone derivatives as a novel non-classical inhibitor scaffold of mycobacterial carbonic anhydrases that lack the sulfonamide/sulfamate group and thus did not affect human carbonic anhydrase II.
Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives
Prachayasittikul, Veda,Pingaew, Ratchanok,Worachartcheewan, Apilak,Nantasenamat, Chanin,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
, p. 247 - 263 (2014/08/05)
A series of 2-substituted amino-3-chloro-1,4-naphthoquinone derivatives (3-12) were synthesized as anticancer agents and tested against four cancer cell lines including HepG2, HuCCA-1, A549 and MOLT-3. The most potent cytotoxic activity against the HepG2,
