cas 776-34-1, 4-Nitro-1-naphthylamine | Articles data

Articles about 776-34-1Total 26 be found

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Synthesis and application of 2-(arylazo)-8-nitronaphtho[1,2-d] thiazole disperse dyes
The paper describes the synthesis of 2-amino-8-nitronaphtho[1,2-d]thiazole and its utilization to prepare a range of heterocyclic azo disperse dyes. These arylazo dyes were studied with respect to their color and constitution relationship. These dyes were applied on polyester fibre and their fastness properties were evaluated.
Rangnekar, Dinesh W.,Maladkar, Gajanan J.
p. 199 - 205
(2000)
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Copper-Catalyzed Regioselective Nitration and Azidation of 1-Naphthylamine Derivatives via Remote C–H Activation
A simple and facile protocols for copper-catalyzed regionselective C4 nitration and azidation of 1-naphthylamines via remote C–H activation that use of pyridyl amide fragment as the removable directing group have been firstly developed. These reactions proceed under mild conditions without any additives, tolerate a wide variety of functional groups, and afford a wide range of products in good to excellent yields. Control experiments suggest that those C–H activation reactions are likely to proceed through a single-electron-transfer (SET) process.
Dou, Yandong,Yin, Biao,Zhang, Pengfei,Zhu, Qing
p. 4571 - 4576
(2018)
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Keap1-Nrf2 PPI inhibitor prodrug and preparation method and application
The invention discloses a Keap1-Nrf2 PPI inhibitor prodrug and a preparation method and application. According to the prodrug P-168 provided by the invention, a polar carboxylic acid group of an active compound 168 is blocked, so that the fat solubility is improved, and the membrane permeability and druggability are effectively improved; the prodrug P-168 is reduced under the condition of high ROS, a pharmacophore 168 and a fluorophore coumarin are released, expression of Nrf2 and downstream genes of Nrf2 is activated, anti-inflammatory activity is brought into play, and meanwhile fluorescenceis released to achieve visual monitoring.
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Paragraph 0031; 0034-0037; 0040; 0041

(2021/02/06)

A hydrogen peroxide responsive prodrug of Keap1-Nrf2 inhibitor for improving oral absorption and selective activation in inflammatory conditions
Transcription factor Nuclear factor erythroid 2-related factor 2 (Nrf2) and its negative regulator, the E3 ligase adaptor Kelch-like ECH-associated protein 1 (Keap1), control the redox and metabolic homeostasis and oxidative stress. Inhibitors of Keap1-Nrf2 interaction are promising in oxidative stress related inflammatory diseases but now hit hurdles. By utilizing thiazolidinone moiety to shield the key carboxyl pharmacophore in Keap1-Nrf2 inhibitor, a hydrogen peroxide (H2O2)-responsive prodrug pro2 was developed. The prodrug modification improved the physicochemical properties and cell membrane permeability of the parent drug. Pro2 was stable and stayed inactive under various physiological conditions, while became active by stimulation of H2O2 or inflammation derived reactive oxygen species. Moreover, pro2 exhibited proper pharmacokinetic profile suitable for oral administration and enhanced anti-inflammatory efficiency in vivo. Thus, this novel prodrug approach may not only provide an important advance in the therapy of chronic inflammatory diseases with high level of H2O2, but also offer a fresh solution to improve the drug-like and selectivity issues of Keap1-Nrf2 inhibitors.
Jiang, Zhengyu,Lu, Mengchen,You, Qidong,Zhang, Xian,Zhao, Jing
(2020/05/18)

Unravelling the mechanism of cobalt-catalysed remote C-H nitration of 8-aminoquinolinamides and expansion of substrate scope towards 1-naphthylpicolinamide
Previously, an unexpected Co-catalysed remote C-H nitration of 8-aminoquinolinamide compounds was developed. This report provided a novel reactivity for Co which was assumed to proceed through the mechanistic pathway already known for analogous Cu-catalysed remote couplings of the same substrates. In order to shed light into this intriguing, and previously unobserved reactivity for Co, a thorough computational study has now been performed, which has allowed for a full understanding of the operative mechanism. This study demonstrates that the Co-catalysed remote coupling does not occur through the previously proposed Single Electron Transfer (SET) mechanism, but actually operates through a high-spin induced remote radical coupling mechanism, through a key intermediate with significant proportion of spin density at the 5- and 7-positions of the aminoquinoline ring. Additionally, new experimental data provides expansion of the synthetic utility of the original nitration procedure towards 1-naphthylpicolinamide which unexpectedly appears to operate via a subtly different mechanism despite having a similar chelate environment.
Chu, Melody,Planas, Oriol,Company, Anna,Ribas, Xavi,Hamilton, Alex,Whiteoak, Christopher J.
p. 534 - 542
(2020/01/21)

A Comparative Assessment Study of Known Small-Molecule Keap1-Nrf2 Protein-Protein Interaction Inhibitors: Chemical Synthesis, Binding Properties, and Cellular Activity
Inhibiting the protein-protein interaction (PPI) between the transcription factor Nrf2 and its repressor protein Keap1 has emerged as a promising strategy to target oxidative stress in diseases, including central nervous system (CNS) disorders. Numerous non-covalent small-molecule Keap1-Nrf2 PPI inhibitors have been reported to date, but many feature suboptimal physicochemical properties for permeating the blood-brain barrier, while others contain problematic structural moieties. Here, we present the first side-by-side assessment of all reported Keap1-Nrf2 PPI inhibitor classes using fluorescence polarization, thermal shift assay, and surface plasmon resonance - and further evaluate the compounds in an NQO1 induction cell assay and in counter tests for nonspecific activities. Surprisingly, half of the compounds were inactive or deviated substantially from reported activities, while we confirm the cross-assay activities for others. Through this study, we have identified the most promising Keap1-Nrf2 inhibitors that can serve as pharmacological probes or starting points for developing CNS-active Keap1 inhibitors.
Tran, Kim T.,Pallesen, Jakob S.,Solbak, Sara M.,Narayanan, Dilip,Baig, Amina,Zang, Jie,Aguayo-Orozco, Alejandro,Carmona, Rosa M. C.,Garcia, Anthony D.,Bach, Anders
p. 8028 - 8052
(2019/10/11)

Sodium persulfate-promoted site-selective synthesis of mononitroarylamines under transition-metal-free conditions
A practical preparation of nitroarylamines from protected arylamines was herein disclosed. In this system, sodium nitrite acted as a nitration reagent in the presence of sodium persulfate without any transition-metal catalysts. This efficient site-selective protocol took place at room temperature for a short time through a free radical pathway.
Xie, De-Xun,Yu, Hui-Juan,Liu, Hui,Xue, Wei-Cai,Qin, Yuan-Shou,Shao, Guang
p. 1157 - 1165
(2019/01/24)

Synthesis method of naphthylamine derivative
The invention discloses a preparation method of a naphthylamine derivative. In the presence of a copper-based catalyst and an oxidant, a picolinamide naphthylamine nitrated product is obtained throughreaction of a nitrate source and picolinamide naphthylamine; furthermore, according to the preparation method, the picolinamide naphthylamine nitrated product is further aminated to further modify naphthylamine. According to the preparation method disclosed by the invention, the naphthylamine is modified according to a C-H activation technology to prepare a series of naphthylamine derivatives. Compared with the conventional method, the preparation method is simpler, more convenient and more efficient.
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Paragraph 0065; 0066; 0067

(2018/08/03)

One-scale basicities of diaminobenzenes and diaminonaphthalenes: from aniline to proton sponge
Basicity constants, pKa, for a wide range of mono-protonated diaminobenzenes and diaminonaphthalenes, including dimethylamino derivatives were for the first time uniformly measured in 20% aqueous ethanol (29 compounds) and 80% aqueous dioxane (39 compounds) spanning from aniline to 1,8-bis(dimethylamino)naphthalene (‘proton sponge’). The dioxane system proved to be more versatile and because of better solubility of N-alkylated polyaminoarenes allowed to add to the same scale some superbasic bis(dialkylamino)-, tetrakis(dialkylamino)-, and hexakis(dialkylamino)naphthalenes, thus extending the scale for almost 10 pKa units, revealing possible limits of basicity changes in aromatic amines. The basicity of reference bases, pyridine and triethylamine, was also measured in these solvent systems. A group of N-alkylated compounds was found to be less basic in aqueous dioxane when compared with their NH2-analogs. This anomaly was not observed in aqueous ethanol. Other basicity trends and correlations between different basicity scales were also discussed. Copyright
Vlasenko, Marina P.,Ozeryanskii, Valery A.
supporting information

(2017/01/17)

Co(II)-Catalyzed Regioselective Cross-Dehydrogenative Coupling of Aryl C-H Bonds with Carboxylic Acids
A cobalt(II)-catalyzed regioselective aryl C-H bond oxygenation between arenes and aryl or aliphatic carboxylic acids under bidendate-chelation assistance is developed. This method provides an efficient approach to acyoxy-substituted arenes with a broad range of functional group tolerance. Furthermore, this reaction system could be further applied to the preparation of polyfunctional naphthylenes.
Lan, Jianyong,Xie, Haisheng,Lu, Xiaoxia,Deng, Yuanfu,Jiang, Huanfeng,Zeng, Wei
supporting information
p. 4279 - 4282
(2017/08/23)

Design, Synthesis, and Initial Evaluation of Affinity-Based Small-Molecule Probes for Fluorescent Visualization and Specific Detection of Keap1
Keap1 is a pluripotent protein which plays a predominant role in cellular homeostasis and stress responses. Given that the cellular environment is quite dynamic and versatile, further investigation of the function of Keap1 depends on tools for specific and real-time detection of Keap1. Herein, we report the development of functional affinity-based small-molecule probes which can overcome some shortcomings of current methods and be applied in further studying the function of Keap1.
Lu, Mengchen,Zhou, Hai-Shan,You, Qi-Dong,Jiang, Zhengyu
p. 7305 - 7310
(2016/08/24)

Polar Recognition Group Study of Keap1-Nrf2 Protein-Protein Interaction Inhibitors
Directly disrupting the Keap1-Nrf2 protein-protein interaction (PPI) has emerged as an attractive way to activate Nrf2, and Keap1-Nrf2 PPI inhibitors have been proposed as potential agents to relieve inflammatory and oxidative stress diseases. In this work, we investigated the diacetic moiety around the potent Keap1-Nrf2 PPI inhibitor DDO1018 (2), which was reported by our group previously. Exploration of bioisosteric replacements afforded the ditetrazole analog 7, which maintains the potent PPI inhibition activity (IC50 = 15.8 nM) in an in vitro fluorescence polarization assay. Physicochemical property determination demonstrated that ditetrazole replacement can improve the drug-like property, including elevation of pKa, log D, and transcellular permeability. Additionally, 7 is more efficacious than 2 on inducing the expression of Nrf2-dependent gene products in cells. This study provides an alternative way to replace the diacetic moiety and occupy the polar subpockets in Keap1, which can benefit the subsequent development of Keap1-Nrf2 PPI inhibitor.
Lu, Meng-Chen,Tan, Shi-Jie,Ji, Jian-Ai,Chen, Zhi-Yun,Yuan, Zhen-Wei,You, Qi-Dong,Jiang, Zheng-Yu
p. 835 - 840
(2016/10/12)

Direct cyanation of picolinamides using K4[Fe(CN)6] as the cyanide source
The efficient, simple, and environment-friendly route of direct cyanation of picolinamides has been developed with nontoxic K4[Fe(CN)6] as the cyanide source through Pdcatalyzed C-H bond activation. A series of N-(naphthalene-1- yl)picolinamide derivatives were successfully transformed to the corresponding cyanation products. The cyanation mechanism has also been speculated.
Guan, Dinghui,Han, Lu,Wang, Lulu,Song, He,Chu, Wenyi,Sun, Zhizhong
supporting information
p. 743 - 745
(2015/06/22)

Probing the structural requirements of non-electrophilic naphthalene-based Nrf2 activators
Activation of the transcription factor Nrf2 has been posited to be a promising therapeutic strategy in a number of inflammatory and oxidative stress diseases due to its regulation of detoxifying enzymes. In this work, we have developed a comprehensive structure-activity relationship around a known, naphthalene-based non-electrophilic activator of Nrf2, and we report highly potent non-electrophilic activators of Nrf2. Computational docking analysis of a subset of the compound series demonstrates the importance of water molecule displacement for affinity, and the X-ray structure of di-amide 12e supports the computational analysis. One of the best compounds, acid 16b, has an IC50 of 61 nM in a fluorescence anisotropy assay and a Kd of 120 nM in a surface plasmon resonance assay. Additionally, we demonstrate that the ethyl ester of 16b is an efficacious inducer of Nrf2 target genes, exhibiting ex vivo efficacy similar to the well-known electrophilic activator, sulforaphane.
Jain, Atul D.,Potteti, Haranatha,Richardson, Benjamin G.,Kingsley, Laura,Luciano, Julia P.,Ryuzoji, Aya F.,Lee, Hyun,Krunic, Aleksej,Mesecar, Andrew D.,Reddy, Sekhar P.,Moore, Terry W.
p. 252 - 268
(2015/09/21)

Structure-Activity and Structure-Property Relationship and Exploratory in Vivo Evaluation of the Nanomolar Keap1-Nrf2 Protein-Protein Interaction Inhibitor
Directly disrupting the Keap1-Nrf2 protein-protein interaction (PPI) is an effective way to activate Nrf2. Using the potent Keap1-Nrf2 PPI inhibitor that was reported by our group, we conducted a preliminary investigation of the structure-activity and structure-property relationships of the ring systems to improve the drug-like properties. Compound 18e, which bore p-acetamido substituents on the side chain phenyl rings, was the best choice for balancing PPI inhibition activity, physicochemical properties, and cellular Nrf2 activity. Cell-based experiments with 18e showed that the Keap1-Nrf2 PPI inhibitor can activate Nrf2 and induce the expression of Nrf2 downstream proteins in an Nrf2-dependent manner. An exploratory in vivo experiment was carried out to further evaluate the anti-inflammatory effects of 18e in a LPS-challenged mouse model. The primary results indicated that 18e could reduce the level of circulating pro-inflammatory cytokines induced by LPS and relieve the inflammatory response. (Chemical Equation Presented).
Jiang, Zheng-Yu,Xu, Li-Li,Lu, Meng-Chen,Chen, Zhi-Yun,Yuan, Zhen-Wei,Xu, Xiao-Li,Guo, Xiao-Ke,Zhang, Xiao-Jin,Sun, Hao-Peng,You, Qi-Dong
supporting information
p. 6410 - 6421
(2015/09/08)

Discovery of potent Keap1-Nrf2 protein-protein interaction inhibitor based on molecular binding determinants analysis
Keap1 is known to mediate the ubiquitination of Nrf2, a master regulator of the antioxidant response. Directly interrupting the Keap1-Nrf2 interaction has been emerged as a promising strategy to develop novel class of antioxidant, antiinflammatory, and anticancer agents. On the basis of the molecular binding determinants analysis of Keap1, we successfully designed and characterized the most potent protein-protein interaction (PPI) inhibitor of Keap1-Nrf2, compound 2, with KD value of 3.59 nM binding to Keap1 for the first time to single-digit nanomolar. Compound 2 can effectively disrupt the Nrf2-Keap1 interaction with an EC50 of 28.6 nM in the fluorescence polarization assay. It can also activate the Nrf2 transcription activity in the cell-based ARE-luciferase reporter assay in a dose-dependent manner. The qRT-PCR results of Nrf2 transcription targets gave the consistent results. These results confirm direct and highly efficient interruption of the Keap1-Nrf2 PPI can be fully achieved by small molecules.
Jiang, Zheng-Yu,Lu, Meng-Chen,Xu, Li-Li,Yang, Ting-Ting,Xi, Mei-Yang,Xu, Xiao-Li,Guo, Xiao-Ke,Zhang, Xiao-Jin,You, Qi-Dong,Sun, Hao-Peng
supporting information
p. 2736 - 2745
(2014/04/17)

Synthesis and characteristics of N-(glyoxyldioxime)-N′-(2- hydroxybenzylidene)-1,4-diaminonaphthalene and its metal complexes
A new vic-dioxime, N-(glyoxyldioxime)-N′-(2-hydroxybenzylidene)-1,4- diaminonaphthalene, was synthesized proceeding from naphthalene. Its complexes of nickel, copper and cobalt were prepared. The vicdioxime and its complexes were charecterized by FT-IR, UV, 1H NMR, mass spectrometry, elemental analysis, DTA/TG analysis techniques and conductometric measurements.
Kaya, Muharrem,Yenikaya, Cengiz,Demir, Ibrahim,Kalfa, Orhan Murat
p. 939 - 945
(2008/12/20)

Highly chemoselective nitration of aromatic amines using the Ph3P/Br2/AgNO3 system
The use of PPh3/Br2/AgNO3 provides a new reagent system for the novel and highly chemoselective nitration of aromatic amines under mild reaction conditions.
Iranpoor, Nasser,Firouzabadi, Habib,Nowrouzi, Najmeh,Firouzabadi, Dena
p. 6879 - 6881
(2007/10/03)

peri-naphthalenediamines: XXXIV. 1,4,5,8-Tetrakis(dimethylamino)naphthalene: Alternative approaches to synthesis
New methods were proposed for synthesizing 1,4,5,8-tetrakis(dimethylamino)naphthalene with an overall yield of 4 to 12% to replace the known procedure ensuring an overall yield of 2%. Catalytic hydrogenation was shown to be inapplicable for preparation of polyaminonaphthalenes from nitro compounds having 3 or 4 nitro gruops in the α-positions. Nucleophilic amination of 1,5-dinitronaphthalene in the system NH2OH/NaOH/MeOH yields 1-amino-4-nitronaphthalene. The nitration of 1,5-bis(p-tolylsulfonylamino)-naphthalene leads to formation of 2,6-dinitro rather than 4,8-dinitro derivative, as it was believed formerly. This was confirmed by transformation of the latter into 1,2,5,6-tetrakis(dimethylamino)naphthalene. 3-Nitro, 2,6-dinitro, 2,6-diamino, and 2,4,6,8-tetranitro derivatives of 1,5-bis(dimethylamino)naphthalene, nitro and amino derivatives of 1,4,5-tris(dimethylamino)naphthalene, and 4,5-diamino-1,8-bis(methylamino)naphthalene were synthesized. By treatment with perchloric acid 1,4,5,8-tetrakis(dimethylamino)naphthalene was oxidized to 2,3-dihydroperimidinium salt.
Sorokin,Ozeryanskii,Pozharskii
p. 699 - 708
(2007/10/03)

A convenient copper-catalyzed direct animation of nitroarenes with 9-alkylhydroxylamines
O-Alkylhydroxylamines, particularly O-methylhydroxylamine, aminate nitroarenes in the presence of a strong base and a copper catalyst to give aminonitroarenes in good yields, ortho- or para-Animation with respect to the nitro group takes place, and in some cases the ortho-aminated product is preferentially obtained. With 3-substituted nitrobenzenes where the substituent has a lone pair of electrons, preferential amination occurs at the 2-position to give the sterically most congested 3c-f, 14 and 22g.
Seko, Shinzo,Miyake, Kunihito,Kavvamura, Norio
p. 1437 - 1444
(2007/10/03)

Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides
A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.
Makosza, Mieczyslaw,Bialecki, Maciej
p. 4878 - 4888
(2007/10/03)

Transformations of Diazonium Salts. III. Transformations, Acid-Base Properties, and Reactivity of Nitronaphthyldiazonium Salts
The transformations in water-alkali media, stability, acid-base properties, and activity in azocoupling of a series of nitronaphthaleneldiazonium salts are studied by preparative, spectroscopic, and kinetic methods. 4-Nitronaphthaleneldiazonium cation shows the highest acidity and the highest activity in azo-coupling. Nitro substitution in other positions much less affects the reactivity of the naphthaleneldiazonium cation. Unlike nitro derivatives of benzene series of diazo compounds, their naphthalene analogs show no effect of isomerism of diazotate anions, other conditions being equal. The experimental evidence does not allows unabiguous assignment of the ntronaphthalene diazotates to Z or E series. The transformations of nitronaphthalenediazonium salts involve addition of hydroxide anion to the ring carbon atom, which results in accumulation of the structural isomer of diazohydroxide. It is assumed that an analogous addition product arises in reaction of the diazonium cation with an azo component, and being an electrophilic species it is capable to enter azo-coupling.
Bagal,Luchkevich,El'tsov
p. 119 - 132
(2007/10/03)

Process for preparing nitroaniline derivatives
A process for preparing a nitroaniline derivative comprising a step of reacting an aromatic nitro compound with an O-alkylhydroxylamine or a salt thereof in the presence of a base and optionally a metallic catalyst, which process is industrially advantageous since it provides the nitroaniline derivative from the aromatic nitro compound in a high yield in one step, and the aminating agent used can be obtained from hydroxylamine at a relatively low cost.
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(2008/06/13)

Process for the preparation of aromatic amines
Electrophilic aromatic compounds can be reacted with sulphenamides in the presence of bases to form the corresponding aromatic amines.
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(2008/06/13)

Amination of Nitroarenes with Sulfenamides via Vicarious Nucleophilic Substitution of Hydrogen
Nitroarenes react with sulfenamides RSNH2 in the presence of strong bases to give p- and o-nitroanilines.
Makosza, Mieczyslaw,Bialecki, Maciej
p. 4784 - 4785
(2007/10/02)

Alkylaminonitrobenzenes by Vicarious Nucleophilic Amination with 4-(Alkylamino)-1,2,4-triazoles
A series of 4-(alkylamino)-1,2,4-triazoles transfer the alkylamino group to the 4-position of nitrobenzene and various 3-substituted nitrobenzenes, with no detectable ortho substitution.By contrast 2-nitrothiophene reacts in the 3-position and 2-nitronaphthalene in the 1-position; 1-nitronaphthalene gives a mixture of products derived from dominant 2- with some 4-substitution.The orientations are discussed and rationalized.
Katritzky, Alan R.,Laurenzo, Kathleen S.
p. 3978 - 3982
(2007/10/02)