175348-78-4Relevant academic research and scientific papers
Synthesis of iodinated naphthoquinones using morpholine-iodine complex
Perez, Alice L.,Lamoureux,Herrera
, p. 3389 - 3397 (2004)
The efficient synthesis of 2-hydroxy-3-iodo-1,4-naphthoquinone (3), 2-amino-3-iodo-1,4-naphthoquinone (4), and 2-iodo-1,4-naphthoquinone (5) have been developed using the parent naphthoquinone in combination with the charge-transfer complex between iodine and morpholine.
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.
supporting information, 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.
P2X7 receptor inhibition by 2-amino-3-aryl-1,4-naphthoquinones
de Luna Martins, Daniela,Borges, Adriel Alves,e Silva, Nayane A. do A.,Faria, Juliana Vieira,Hoelz, Lucas Villas B?as,de Souza, Hellen Valério Chaves Moura,Bello, Murilo Lamim,Boechat, Nubia,Ferreira, Vitor Francisco,Faria, Robson Xavier
supporting information, (2020/10/06)
Extracellular ATP activates purinergic receptors such as P2X7, cationic channels for Ca2+, K+, and Na+. There is robust evidence of the involvement of these receptors in the immune response, so P2X7 receptors (P2X7R) are considered a potential therapeutic target for the development of anti-inflammatory drugs. Although there are many studies of the anti-inflammatory properties of naphthoquinones, these molecules have not yet been explored as P2X7 antagonists. In previous work, our group prepared 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones and studied their action on P2X7R. In this paper, eight 2-amino-3-aryl-1,4-naphthoquinones were evaluated to identify the inhibitory activity on P2X7R and the toxicological profile. Three analogues (AD-4CN, AD-4Me, and AD-4F) exhibited reduced toxicity for mammalian cells with CC50 values higher than 500 μM. These three 3-substituted 2-amino-1,4-naphthoquinones inhibited murine P2X7R (mP2X7R) in vitro. However, the analogues AD-4CN and AD-4Me showed low selectivity index values. AD-4F inhibited both mP2X7R and human P2X7R (hP2X7R) with IC50 values of 0.123 and 0.93 μM, respectively. Additionally, this analogue exhibited higher potency than BBG at inhibiting the ATP-induced release of IL-1β in vitro. Carrageenan-induced paw edema in vivo was reversed for AD-4F with an ID50 value of 11.51 ng/kg. Although AD-4F was less potent than previous 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones such as AN-04 in vitro, this 3-substituted 2-amino-1,4-naphthoquinone revealed higher potency in vivo to reduce the edematogenic response. In silico analysis suggests that the binding site of the novel 2-amino-3-aryl-1,4-naphthoquinone derivatives, including all the tautomeric forms, is located in the pore area of the hP2X7R model. Based on these results, we considered AD-4F to be a satisfactory P2X7R inhibitor. AD-4F might be used as a scaffold structure to design a novel series of inhibitors with potential inhibitory activity on murine (mP2X7R) and human (hP2X7R) P2X7 receptors.
Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones-green palladium-catalysed Suzuki cross coupling
Louvis, Aline Da R.,Silva, Nayane A. A.,Semaan, Felipe S.,Da Silva, Fernando De C.,Saramago, Gabriela,De Souza, Laís C. S. V.,Ferreira, Bruno L. A.,Castro, Helena C.,Salles, Juliana P.,Souza, André L. A.,Faria, Robson X.,Ferreira, Vitor F.,Martins, Daniela De L.
, p. 7643 - 7656 (2016/09/28)
Quinones are important scaffolds that are present in a variety of natural products or synthetic bioactive molecules. Arylation is an important strategy for accomplishing structural modifications, leading to new potential candidates for use as drugs. In the present work, palladium-catalysed, ligandless and phosphine-free Suzuki coupling reactions between 2-hydroxy-3-iodo-1,4-naphthoquinone and boronic acids were employed to prepare several 2-hydroxy-3-aryl-1,4-naphthoquinones in aqueous conditions using microwave irradiation or conventional heating. Because of the biological activities of quinones, which are related to their ability to accept electrons to form semiquinones and hydroquinones, the electrochemical behaviour of the synthesized molecules was investigated. The Osiris and Molinspiration Cheminformatics programs, utilizing in silico analyses, imply that these naphthoquinones are candidates for use as drugs which was reinforced by the outcomes of the in vitro antifungal and trypanocidal activity tests. Our in vitro data indicated a MIC value of 8 μg mL-1 against Candida albicans ATCC 24433 strains, and an EC50 of 0.67 μM with respect to trypanocidal activity against Trypanosoma cruzi epimastigote strains (Y).
Aryliodonium derivatives of 2-amino-1,4-quinones: Preparation and reactivity
Papoutsis, Ioannis,Spyroudis, Spyros,Varvoglis, Anastasios,Raptopoulou, Catherine P.
, p. 6097 - 6112 (2007/10/03)
The reaction of 2-amino-1,4-quinones with [(hydroxy)(tosyloxy)iodo]arenes affords stable 2-amino-3-aryliodonio-1,4- quinones in high yields. The latter, upon treatment with alkali, are converted to the corresponding zwitterionic 3-aryliodonio-1,4-quinone-2-imides. This new class of compounds exhibits an interesting reactivity: upon heating, aryl migration from iodine to nitrogen is observed, while photochemical reaction with aromatic compounds and 2,3-dihydrofuran leads to substitution products. Nucleophilic attack of sodium alkoxides on these zwitterions results in opening of the quinone ring affording synthetically interesting multifunctional products.
3-Aryliodonio-1,4-naphthoquinone-2-imides: A new class of aryliodonium 1,4 dipoles
Papoutsis, Ioannis,Spyroudis, Spyros,Varvoglis, Anastasios
, p. 913 - 916 (2007/10/03)
The synthesis of a new class of zwitterionic aryliodonium compounds from 2-amino-1,4-naphthoquinone and [(hydroxy)(tosyloxy)iodo]arenes is described. These dipoles exhibit an interesting reactivity under thermal and photochemical conditions.
