2348-81-4Relevant articles and documents
An expeditious and green one-pot synthesis of 12-substituted-3,3-dimethyl-3,4,5,12-tetrahydrobenzo[b]acridine-1,6,11(2H)-triones
Kamalifar, Saiedeh,Kiyani, Hamzeh
, p. 5975 - 5987 (2019)
In this study, several new 12-aryl/heteroaryl-3,3-dimethyl-tetrahydrobenzo[b]acridine-1,6,11(2H)-trione heterocyclic compounds that can be considered as 1,4-naphthoquinone fused with 4-substituted 7,7-dimethyl-4,6,7,8-tetrahydroquinolin-5(1H)-ones, have been synthesized through the three-component cyclocondensation of benzaldehydes/heteroaldehydes, 2-amino-1,4-naphthoquinone, and dimedone. The pot-, atom-, and step-economy reactions were implemented under reflux conditions. One of the most important aspects of this reaction is the use of ethanol as the reaction medium taking into account the principles of green chemistry. Not using a catalyst in this type of reactions is also significant from the standpoint of green chemistry. The protocol developed in this study has the benefits of the simplicity, no use of chromatographic methods for purification, structural diversity, employing non-toxic solvent, good-to-high yields, safety, and using cost-effective solvent. The structures of the newly synthesized 1,4-naphthoquinone fused with 4-substituted 7,7-dimethyl-4,6,7,8-tetrahydroquinolin-5(1H)-ones were confirmed employing spectroscopic data as well as elemental analysis.
Amination of Naphthoquinones with Azidotrimethylsilane
Husu, Breda,Kafka, Stanislav,Kadunc, Zdenka,Tisler, Miha
, p. 215 - 222 (1988)
A new method for the synthesis of aminonaphthoquinones from 1,2- or 1,4-naphthoquinones and azidotrimethylsilane is described.In a similar manner 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone was transformed into 2-amino-3-hydroxy-1,4-naphthoquinone.The mechanism of these transformations and the formation of by-products are discussed. - Keywords: Amination with direct amino group introduction; Aminonaphthoquinones
Reaction of hydroxylamines with 1,4-quinones: A new direct synthesis of aminoquinones
Bittner,Lempert
, p. 917 - 919 (1994)
A novel one-step amination of 1,4-naphthoquinones and 1,4-benzoquinones is described. O-Benzylhydroxylamine was found to be the best aminating agent while O-methylhydroxylamine, carboxymethoxylamine and free hydroxylamine are less effective.
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.
Benzoquinoxalinone compound as well as synthesis method and application thereof
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Paragraph 0105-0106, (2021/11/10)
The invention discloses a series of benzoquinoxalinone compounds as well as a synthesis method and application thereof, in particular to compounds of formula (I) as well as synthesis method and application thereof in treating cancer
The one-pot synthesis of amidonapthoquinones from aminonaphthoquinones
Rainier, Jon D.,Yin, Jinya
, (2020/03/23)
Described here is a one-pot method of synthesizing amidonaphthoquinones from the corresponding aminonaphthoquinones. The scope of amides that can be synthesized using this methodology is relatively broad and the yield of product is higher than the traditional methods of synthesizing these substrates. 2009 Elsevier Ltd. All rights reserved.
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.
Ruthenium(II)-Catalyzed Double Annulation of Quinones: Step-Economical Access to Valuable Bioactive Compounds
da Silva Júnior, Eufranio N.,de Carvalho, Renato L.,Almeida, Renata G.,Rosa, Luisa G.,Fantuzzi, Felipe,Rogge, Torben,Costa, Pedro M. S.,Pessoa, Claudia,Jacob, Claus,Ackermann, Lutz
supporting information, p. 10981 - 10986 (2020/07/13)
Double ruthenium(II)-catalyzed alkyne annulations of quinones were accomplished. Thus, a strategy is reported that provides step-economical access to valuable quinones with a wide range of applications. C?H/N?H activations for alkyne annulations of naphthoquinones provided challenging polycyclic quinoidal compounds by forming four new bonds in one step. The singular power of the thus-obtained compounds was reflected by their antileukemic activity.
Synthetic method for NSC128981
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Paragraph 0029-0032, (2019/11/13)
The invention discloses a synthetic method for NSC128981. The structure of NSC128981 is as shown in a formula (I). The synthetic method comprises the following steps: subjecting naphthoquinone (II) toan amination reaction to obtain 2-amino-1,4-naphthoquinone (III); subjecting 2-mino-1,4-naphthoquinone (III) to p-chlorophenylthiolation to obtain 2-amino-3-p-chlorophenylthio-1,4-naphthoquinone (IV); and adding an acetylation agent into 2-amino-3-p-chlorophenylthio-1,4-naphthoquinone (IV) under acidic conditions for an acetylation reaction so as to obtain NSC128981 (I). A reaction formula is asdescribed in the specification. The method of the invention has the advantages of simple steps, low price and easy availability of raw materials, high yield, high product purity, low cost and the like, and avoids the use of toxic or corrosive chlorination reagents in the prior art.
One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones
Yuan, Jiaqi,He, Qian,Song, Shanshan,Zhang, Xiaofei,Miao, Zehong,Yang, Chunhao
supporting information, (2019/08/30)
Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency,mild conditions, and benign functional group compatibilitywas reported. Avariety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.
