cas 93-05-0, N,N-Diethyl-1,4-phenylenediamine

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Photoreductive chlorine elimination from a Ni(iii)Cl2complex supported by a tetradentate pyridinophane ligand
Herein we report the isolation, characterization, and photoreactivity of a stable NiIIIdichloride complex supported by a tetradentate pyridinophane N-donor ligand. Upon irradiation, this complex undergoes an efficient photoreductive chlorine elimination reaction, both in solution and the solid-state. Subsequently, the NiIIICl2species can be regeneratedviaa reaction with PhICl2
Mirica, Liviu M.,Na, Hanah,Rath, Nigam P.,Tang, Fengzhi,Watson, Michael B.
supporting information
p. 7264 - 7267
(2021/07/28)

Optimization of WZ4003 as NUAK inhibitors against human colorectal cancer
NUAK, the member of AMPK (AMP-activated protein kinase) family of protein kinases, is phosphorylated and activated by the LKB1 (liver kinase B1) tumor suppressor protein kinase. Recent work has indicated that NUAK1 is a key component of the antioxidant stress response pathway, and the inhibition of NUAK1 will suppress the growth and survival of colorectal tumors. As a promising target for anticancer drugs, few inhibitors of NUAK were developed. With this goal in mind, based on NUAK inhibitor WZ4003, a series of derivatives has been synthesized and evaluated for anticancer activity. Compound 9q, a derivative of WZ4003 by removing a methoxy group, was found to be the most potential one with stronger inhibitory against NUAK1/2 enzyme activity, tumor cell proliferation and inducing apoptosis of tumor cells. By in vivo efficacy evaluations of colorectal SW480 xenografts, 9q suppresses tumor growth more effectively with an excellent safety profile in vivo and is therefore seen as a suitable candidate for further investigation.
Yang, Huali,Wang, Xiaobing,Wang, Cheng,Yin, Fucheng,Qu, Lailiang,Shi, Cunjian,Zhao, Jinhua,Li, Shang,Ji, Limei,Peng, Wan,Luo, Heng,Cheng, Maosheng,Kong, Lingyi
(2020/12/15)

Co/Cu bimetallic ZIF as New heterogeneous catalyst for reduction of nitroarenes and dyes
Nowadays one of the great challenges is to design new bimetallic catalysts with enhanced catalytic activity, selectivity and recycling properties. In this work, the preparation of new Co/Cu bimetallic Zeolitic Imidazolate Framework (Co-Cu/ZIF) as an efficient catalyst for the reduction of nitro compounds and organic dyes is described. Co-Cu/ZIF was characterized with different techniques such as SEM, TEM, XRD, XPS, TGA, FT-IR and UV–vis absorption indicating formation of entirely uniform cubic particles. Using this catalyst, structurally different aromatic nitro compounds were reduced efficiently to corresponding amines in excellent yields. Kinetic studies revealed that the reduction rates of nitrophenol isomers follow 3-NP > 4-NP > 2-NP order. The catalytic activity of Co-Cu/ZIF was further investigated in the reduction of organic dyes such as methyl orange (MO) and rhodamine B (RhB). This catalyst was recycled for at least ten runs in the reduction of 4-nitrophenol without a noticeable decrease in activity and reused catalyst was characterized.
Gholinejad, Mohammad,Naghshbandi, Zhwan,Sansano, José M.
(2020/02/04)

Discovery of benzo[d]oxazole derivatives as the potent type-I FLT3-ITD inhibitors
Fms-like tyrosine kinase 3 (FLT3) has been considered as a potential drug target for the treatment of acute myeloid leukemia (AML), because of its high and aberrant expression in AML patients, especially the patients with FLT3-ITD mutation. Initiating from a hit compound (IC50: 500 nM against FLT3-ITD), a series of compounds were designed and synthesized based on benzo[d]oxazole-2-amine scaffold to discover new potent FLT3-ITD inhibitors. During the medicinal chemistry works, flexible molecular docking was used to provide design rationale and study the binding modes of the target compounds. Through the mixed SAR exploration based on the enzymatic and cellular activities, compound T24 was identified with potent FLT3-ITD inhibitory (IC50: 0.41 nM) and anti-proliferative (IC50: 0.037 μM against MV4-11 cells) activities. And the binding mode of T24 with “DFG-in” FLT3 was simulated by a 20-ns molecular dynamics run, providing some insights into further medicinal chemistry efforts toward novel FLT3 inhibitors in AML therapy.
Bao, Jiyin,Liu, Haichun,Zhi, Yanle,Yang, Wenqianzi,Zhang, Jiawei,Lu, Tao,Wang, Yue,Lu, Shuai
(2019/09/30)

Preparation method of cationic blue dye
The invention belongs to the technical field of dyes, and particularly relates to a preparation method of a cationic blue dye. According to the invention, a compound II is used as a diazonium component and a compound I is used as a coupling component for synthesizing the cationic blue dye for the first time; and the method has the advantages of simple process, environmental friendliness, high product purity, high yield and the like. The results of multiple production experiments with scales not below pilot tests show that mother liquor (such as mother liquor in steps 2, 3 and 4) in the reaction process can be cyclically used 6-8 times without treatment, so the amount of high-salt, high-COD and high-chroma wastewater is greatly reduced, a working environment is effectively improved while product yield is further increased and reaction reagent cost is saved, and the product still keeps high purity; and thus, product quality is guaranteed, production cost is reduced, and obvious economicbenefits, social benefits and environmental benefits are produced.
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(2020/02/14)

Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates
A chemoselective sequential one-pot coupling protocol was developed for preparing several amino-anilines in high yield as building blocks for active pharmaceutical ingredients (APIs). Site (Cl vs Br on electrophile) and nucleophile (amine vs imine) selectivity is dictated by the catalyst employed. A Pd-crotyl(t-BuXPhos) precatalyst selectively coupled the Ar-Br of the polyhaloarene with benzophenone imine, even in the presence of a secondary amine, while Pd-based RuPhos or (BINAP)Pd(allyl)Cl coupled the Ar-Cl site with secondary amines.
Mikhailine, Alexandre A.,Grasa Mannino, Gabriela A.,Colacot, Thomas J.
supporting information
p. 2301 - 2305
(2018/04/30)

A NIR turn-on fluorescent probe applied in cytochrome P450 reductase detection and hypoxia imaging in tumor cells
In?vivo monitoring of the hypoxic area is urgently required. Near infrared (NIR) fluorescence-active fluorophores with excellent photo stability are preferable for in?vivo imaging. A novel rational designed turn-on fluorescent probe with high selectivity and long-wavelength was synthesized which was applied in bioreductase (cytochrome P450 reductase which overexpressed in tumor cells) and hypoxia detection. The NIR probe (AZO-DCM) is based on a photo stability fluorophore dicyanomethylene-4H-pyran dye (DCM) with an azo bond as probe quencher and hypoxic trigger. After reacted with cytochrome P450 reductase, azo bond was cleaved and DCM released with fluorescent on. The designed probe showed high anti-interference ability which cannot disturb by many interfering substances, such as biothiols, inorganic salts (included sulfite salt) and amino acid. AZO-DCM performed good selectivity and sensitivity to cytochrome P450 reductase and hypoxia. The fluorescent intensity was increased more than 150-fold after response to cytochrome P450 reductase and NADH system in 4?min. The reaction mechanism also proved by HPLC experiment. Probe AZO-DCM displayed excellent properties in identifying different hypoxic status of tumor cells in?vivo.
Cui, Lei,Shi, Yanping,Zhang, Shuping,Yan, Luliang,Zhang, Huan,Tian, Zhenran,Gu, Yingying,Guo, Ting,Huang, Junhai
p. 587 - 592
(2017/01/03)

Discovery of Potent, Selective Stem Cell Factor Receptor/Platelet Derived Growth Factor Receptor Alpha (c-KIT/PDGFRα) Dual Inhibitor for the Treatment of Imatinib-Resistant Gastrointestinal Stromal Tumors (GISTs)
Stem cell factor receptor (c-KIT) and platelet derived growth factor receptor alpha (PDGFRα) kinases play an important role in gastrointestinal stromal tumors (GISTs). Here, we have discovered an c-KIT/PDGFRα dual inhibitor, compound 31, with single-digit nanomolar potency against c-KIT and PDGFRα. Compared to Imatinib (1), 31 showed better antiproliferative efficacy against various TEL-c-KIT/PDGFRα-BaF3 isogenic cells, including three 1-resistant BaF3 cell lines, as well as against GIST-T1 and GIST-882 cell lines. Furthermore, compound 31 showed a good KinomeScan selectivity (468 kinases) (S score (1) = 0.01 at 1 μM concentration), good metabolic stability in liver microsomes, and no hERG inhibitory activity. It was worth noting that 31 inhibited GIST-T1 tumor growth (TGI = 81.5%) and even the BaF3-TEL-cKIT-T670I tumor progression (TGI = 41.9%, 1-resistant GISTs) at a dosage of 100 mg/kg/day without exhibiting apparent toxicity.
Lu, Yanli,Mao, Fei,Li, Xiaokang,Zheng, Xinyu,Wang, Manjiong,Xu, Qing,Zhu, Jin,Li, Jian
supporting information
p. 5099 - 5119
(2017/06/28)

Combination of 4-anilinoquinazoline, arylurea and tertiary amine moiety to discover novel anticancer agents
In present study, 4-anilinoquinazolines scaffold, arylurea and tertiary amine moiety were combined to design, synthesize gefitinib analogs and discover novel anticancer agents. A series of 4-anilinoquinazoline derivatives (1, 2, 3 and 4) bearing arylurea and tertiary amine moiety at its 6-position were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against A431 cell and A549 cell. The SAR of the title compounds was discussed. The compounds 2d, 2i and 2j with potent antiproliferative activities were evaluated their inhibitory activity against EGFR-TK. Compound 2j displayed potent inhibitory activity against EGFR-TK. In addition, compound 2j, at 50 mg/kg, can completely inhibit cancer growth in established nude mouse A549 xenograft model in vivo. These results suggest that the 4-anilinoquinazoline derivatives bearing diarylurea and tertiary amino moiety at its 6-position can serve as anticancer agents and EGFR inhibitors.
Zuo, Sai-Jie,Zhang, Sai,Mao, Shuai,Xie, Xiao-Xiao,Xiao, Xue,Xin, Min-Hnag,Xuan, Wei,He, Yuan-Yuan,Cao, Yong-Xiao,Zhang, San-Qi
p. 179 - 190
(2015/12/31)

TGF-beta SIGNAL TRANSDUCTION INHIBITOR
The present invention provides a compound represented by the following formula (I) or a physiologically acceptable salt thereof, and use thereof for the prophylaxis or treatment of TGF-β-related diseases: wherein Y is a hydrogen atom and the like; R2 is and the like; R3 is —NR8—R9— and the like; R4, R5, R6 and R7 are the same or different and each is a hydrogen atom and the like; and X is and the like.
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Paragraph 0219; 0220; 0221; 0222

(2013/03/26)

2,2-Bis(ethoxycarbonyl)vinyl (BECV) as a versatile amine protecting group for selective functional-group transformations
A 2,2-Bis(ethoxycarbonyl) vinyl- (BECV) group was used for the selective protection of amines at room temperature in the presence of potentially interfering functional groups such as OH, SH, COOH as well as other NH 2 groups. Several functional group transformations such as esterification, O-alkylation, O-acylation, N-alkylation, N-acylation, S-alkylation can selectively be carried out in the presence of the BECV group. The selective deprotection of the BECV group was achieved in a short time using ethylenediamine at room temperature while several other functional groups such as benzoate, aliphatic esters, amides and ethers remain intact. The BECV group shows orthogonal stability against the common protecting groups such as Fmoc, Cbz and Boc.
Ilangovan, Andivelu,Kumar, Rajendran Ganesh
supporting information; experimental part
p. 2938 - 2943
(2010/07/02)

1,3-Dihydroxybenzene derivatives and colorants containing said compounds
1,3-Dihydroxybenzene derivatives of general formula (I) or (Ia) or physiologically tolerated, water-soluble thereof wherein R′1 denotes substituted pyridyl group, a pyrimidyl group, a group of formula (IIa) or (IIIa) and the dyeing agents for keratin fibers containing these compounds.
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(2008/06/13)

Reduction of nitrosoarenes into anilines by Al/NH4Cl in refluxing methanol
A simple, cost-effective method for the reduction of nitrosoarenes by aluminium in the presence of ammonium chloride in refluxing methanol to give anilines is reported.
Nagaraja,Pasha
p. 593 - 594
(2007/10/03)

Reductive coupling of nitroarenes to hydrazoarenes with aluminium and potassium hydroxide in methanol
A simple and inexpensive procedure for the reductive coupling of nitroarenes to hydrazoarenes with aluminium and potassium hydroxide in methanol at ambient temperature is reported. The coupling is proposed to proceed by single electron transfer from aluminium.
Khurana, Jitender M.,Singh, Sarika
p. 1893 - 1895
(2007/10/03)

3-substituted para-aminophenols
The invention concerns the use of a 3-substituted para-aminophenol as an oxidation dye precursor for dyeing keratinous fibres, in particular human hair. The 3-substituted para-aminophenol has formula: STR1 where R1 represents alkyl, alkenyl, mono- or polyhydroxyalkyl, nitrile, cyanoalkyl, halogenoalkyl, aminoalkyl or alkoxyalkyl and R2 represents hydrogen, alkyl or mono- or polyhydroxyalkyl, provided that when R2 is hydrogen R1 is not methyl or trifluoromethyl, and to addition salts thereof with an acid. The invention also concerns dye compositions containing compound (I). The invention further concerns novel 3-substituted para-aminophenols.
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(2008/06/13)

Alkali-induced Formation of ortho-Semidines from 3-Nitro- and 3-Azocarbazoles - Synthesis of 8,16-Dialkyldiindolo[3,2-a,d]phenazines
The ortho-semidines 9-alkyl-4-(9-alkylcarbazol-3-ylamino)-3-aminocarbazoles (2a-d) are formed either by reduction of 9-alkyl-3-nitro-carbazoles (1a-d) or of the azo-(6) or the azoxycarbazoles (7) with zinc in alkaline alcoholic solution. It could be shown by cross experiments that the semidines 2 result from an intramolecular rearrangement. The compounds 2a-d are oxidized by air or H2O2 to the 8,16-dialkyldiindolo[3,2-a,d]phenazines (3a-d). Reduction of 1a-c with Raney-alloy affords the 9-alkyl-3-azoxycarbazoles 7a-c in good yields.
Fanghaenel,Chtcheglov
p. 731 - 737
(2007/10/03)

Methine compounds
Methine compounds are described, which can be represented by general formula [Ic]: STR1
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(2008/06/13)

Titanium complex-catalyzed borohydride reduction of azobenzenes
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Dosa, Peter,Kronish, Ian,McCallum, Jeremy,Schwartz, Jeffrey,Barden, Michael C.
p. 4886 - 4887
(2007/10/03)

Dye-donor element for use in thermal dye sublimation transfer
Dye-donor element for use according to thermal dye sublimation transfer, said dye-donor element comprising a support provided with a dye layer containing a dye dispersed in a polymeric binder, characterized in that said dye corresponds to the following formula (I) wherein, R1, R2 and R3 independently represent hydrogen, halogen, nitro, an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group, a alkylthio group, a arylthio group, an acylamino group, a sulfamoyl group, a carbamoyl group, which groups may be substituted, or R2 and R3 together can form a saturated or aromatic or heterocyclic ring fused-on the cyclohexadiene ring, which ring may be substituted; wherein, R4 represents hydrogen, an alkyl group, a cycloalkyl group, an aryl group, which groups may be substituted, SO2R10, COR10, POR10R11;, R5 represents hydrogen, halogen, nitro, cyano, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, which groups may be substituted;, R6 and R6'independently represent an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group or a heterocyclic group, which groups may be substituted, or R6 and R6'together form a 5- or 6-membered ring, which ring may be substituted;, R7 represents an alkyl group, an aryl group, a cycloalkyl group, which groups may be substituted;, R8 and R9 independently represent hydrogen, an alkyl group,an aryl group, a cycloalkyl group, which groups may be substituted, or R8 and R9 together can form a heterocyclic ring, which ring may be substituted;, R10 and R11 independently represent an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group or a heterocyclic group, which groups may be substituted, or R10 and R11 together form a 5- or 6-membered ring, which ring may be substituted;, K represents wherein:, R12 and R13 (independently) represent hydrogen, an alkyl group, an aryl group, a heterocyclic group, which groups may be substituted, or R12 and R13 together represent the necessary atoms to close a heterocyclic ring, which ring may be substituted, or R12 and/or R13 together with R14 and/or R17 represent the necessary atoms to close a ring fused-on the benzene ring, which ring may be substituted;, R14, R15, R16 and R17 independently represent hydrogen, hydroxy, halogen, an alkyl group, a cycloalkyl group, an aryl group, an alkyloxy group, an aryloxy group, a carbamoyl group, a sulfamoyl group, which groups may be subsituted which groups may be substituted, NH-SO2R18, NH-COR18, O-SO2R18, O-COR18, or R14 and R15 together and/or R16 and R17 together represent the necessary atoms to close (a) ring(s) fused-on the benzene ring or R14 and/or R17 together with R12 and/or R13 represent the necessary atoms to close a heterocyclic ring fused-on the benzene ring, which groups may be substituted;, R18 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, a heterocyclic group, which groups may be substituted.
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(2008/06/13)

Kinetics of Hydrolysis of Some New Heterocyclic Azomethines
Kinetics of base hydrolysis of new heterocyclic azomethines derived from active methyl quaternary salts and aromatic nitroso compounds were investigated in the presence of 70percent (wt/wt) water-methanol.The base hydrolysis of these compounds is strictly first-order with respect to OH- and azomethine.The rate determining step is suggested to be the attack of the hydroxide ion on the free base.Effects of water content and nature of organic hydroxylic solvent have been studied.It is concluded that specific solute-solvent interactions through dispersion forces play a major role in the base hydrolysis rate of the azomethines investigated.The effect of pH (2.98 - 12.24) on hydrolysis rates of compounds having a diethylamino substituent in the presence of 30percent methanol has been studied.In acidic media, the rate determining step is probably the water attack on the protonated substrate.
Mahmoud, Mohamed Rafat,Hamed, Maher Mohamed Ahmed,Shaker, Ali Mohamed
p. 765 - 776
(2007/10/02)

Mechanismus der quasi-homogenen Oxidation von p-Phenylendiaminen mit Silbernitrat
The redox reaction between p-phenylenediamines and silver nitrate in aqueous acid solution was observed optically in a double wavelength photometer.In presence of a nobel metal plate or larger clusters of silver, production of p-semiquinonediimines respective silver starts immediately, whereas without clusters present at the beginning of the reaction the maximum reaction rate is attained only after a certain induction period.The length of this induction period depends on the pH and the concentration of p-phenylenediamine, but not on the silver ion concentration.It is not the number of the clusters that influences the induction period, but their size.The rate of the main reaction, however, is proportional to the number of the clusters formed.In dilute solutions the main reaction is of first order concerning both of the two reactants, in concentrated solution, however, it is of smaller order. - Keywords: Oxidation / Cluster / p-Phenylenediamines / Silver / Photographic development
Nickel, U.,Ruehl, N.,Zhou, B. M.
p. 33 - 52
(2007/10/02)

THE PHOTOCHEMISTRY OF AZO DYES. PHOTOISOMERISATION VERSUS PHOTOREDUCTION FROM 4-DIETHYLAMINOAZOBENZENE AND 4-DIETHYLAMINO-4'-METHOXYAZOBENZENE.
4-Diethylaminoazobenzene (2) and 4-diethylamino-4'-methoxyazobenzene (3) undergo geometrical isomerization with a quantum yield of almost unity by irradiation in the visible region, and, with lower efficiency, by irradiation at a shorter wavelength or sensitization both with high and low energy hydrocarbons.These dyes are also photoreduced, this time however only by irradiation at λ -4-4 x 10-2).Photoreduction also takes place by energy transfer from high enegy sensitizers as well as by radical initiation by ketones.It is concluded that the lowest singlet and triplet states of these azobenzene derivatives, which are reasonable models for commercially useful monoazo-dyes, are only capable of geometrical isomerization, whereas hydrogen abstraction takes place from the high-lying triplet state of both the trans- and cis-configuration of these dyes.
Albini, Angelo,Fasani, Elisa,Pietra, Silvio
p. 1021 - 1024
(2007/10/02)

1- und 2-Elektronenschritte bei der Oxidation substituierter Paraphenylendiamine mit verschiedenen Oxidationsmitteln. II. Reaktionen mit Hexacyanoferrat
The oxidation kinetics of several N- and ring-alkylated p-phenylenediamines with hexacyanoferrate(III) (F3) was studied in the pH-range 2,5-9 by means of a multimixing stopped flow technique which is described in detail.The p-phenylene diamine-derivatives (R) are oxidized via reversible one-electron steps to the semiquinone diimine radical S (rate constants k1, k-1) and the quinone diimine T (rate constants k2, k-2). - k1 and k-1 could be measured directly for all compounds, k2 and k-2 for two derivatives. - Only the unprotonated species of R, S, T, F3 are reactive.The reduction is possible by the unprotonated Fe(CN)64- (F2) and by its protonated form F2H.The complexes of F2 with alkali ions are inactive.In this way the respective association constants could be calculated.The kinetics of the reaction was compared with the thermodynamics, represented by potential-pH-diagrams. - The activation parameters of the reaction of p-phenylene diamine-derivatives with F3, F2 and also with iodine were measured.The activation energies of the second step (k2, k-2) are negligible. - Both oxidants attack the alkylated aminogroup of the p-phenylene diamine derivatives.The radical cation is deprotonated before it is oxidized.
Nickel, Ulrich,Jaenicke, Walther
p. 695 - 701
(2007/10/02)

The Photochemistry of Azo-dyes. The Wavelength-dependent Photoreduction of 4-Diethylamino-4'-nitroazobenzene
4-Diethylamino-4'-nitroazobenzene (I) is photoreduced upon irradiation at 254 nm, and in alcohols, also at 313 nm, while visible light is inactive.The products are the corresponding hydrazo-derivative (II) or the amines (III) and (IV).Triplet sensitizers
Albini, Angelo,Fasani, Elisa,Pietra, Silvio
p. 1393 - 1396
(2007/10/02)

INFLUENCE OF STRUCTURE OF SOME AZO COMPOUNDS ON THEIR ACID-BASE PROPERTIES AND REDUCTION
A series of azo compounds were prepared and their acid-base equilibria in aqueous-alcoholic solutions were studied in dependence on the pH.The oxidation-reduction properties of the compounds and of their reduction products were examined polarographically and by preparative electroreduction.The effect of substituents at the azo group on the examined properties of the compounds is discussed.
Madajova, Vlasta,Zelensky, Imrich
p. 987 - 1001
(2007/10/02)