72767-62-5Relevant academic research and scientific papers
Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- And Alkynylnaphthoquinones and Derivatives
Demidoff, Felipe C.,Rodrigues Filho, Eduardo José P.,De Souza, Andréa Luzia F.,Netto, Chaquip D.,De Carvalho, Leandro L.
, p. 4097 - 4109 (2021/08/31)
Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free Cu I -mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.
Tertiary amines as vinyl source for the formations of aryl or pyrrole ring on amido-substitued 1,4-quinone with the assistance of palladium salt
Jhou, Jia-Nan,Cheng, Chiu-Wen,Hong, Fung-E
, p. 2118 - 2128 (2020/06/17)
The one-pot synthesis of 3-isopropyl-6-methyl-1H-benzo[f]indole-4,9-dione (3e), N-(4-[isopentylamino]-3,6-dioxocyclohexa-1,4-dien-1-yl)acetamide (4d), 2-(isopentylamino)-6-methylnaphthalene-1,4-dione (5b), and 2-(4-acetamido-3,6-dioxocyclohexa-1,4-dien-1-
Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents
Acu?a, Julio,Piermattey, Jhoan,Caro, Daneiva,Bannwitz, Sven,Barrios, Luis,López, Jairo,Ocampo, Yanet,Vivas-Reyes, Ricardo,Aristizábal, Fabio,Gaitán, Ricardo,Müller, Klaus,Franco, Luis
, (2018/02/06)
Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.
Photo-induced Molecular Transformations, Part 123. One-Step Synthesis of 1H-Benzindole-4,9-diones by a New Regioselective Photoaddition of 2-Amino-1,4-naphthoquinone with Various Alkenes and Its Application to the One-Step Synthesis of Kinamycin Skeleton
Kobayashi, Kazuhiro,Takeuchi, Hiroyasu,Seko, Shinzo,Suginome, Hiroshi
, p. 1091 - 1094 (2007/10/02)
2,3-Dihydro-1H-benzindole-4,9-diones are formed in one-step in 45-82percent yields by an unprecedented -type regioselective photoaddition of 2-amino-1,4-naphthoquinone with various electron-rich alkenes and the adducts derived from aminonaphthoquinone with vinyl ethers and vinyl acetate to give 1H-benzindole-4,9-diones including a benzindole-dione with a kinamycin skeleton in 33-72percent yields.A probable pathway leading to the formation of the dihydroindole-dione involving air oxidation of an intermediary hydroquinone is proposed.
