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Design, synthesis and biological evaluation of benz-fused five-membered heterocyclic compounds as tubulin polymerization inhibitors with anticancer activities
A series of benz-fused five-membered heterocyclic compounds were designed and synthesized as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 4d displayed the highest antiproliferative activity against four cancer cell lines with an IC50 value of 4.9?μM in B16-F10 cells. Compound 4d effectively inhibited tubulin polymerization in vitro (IC50 of 13.1?μM). Further, 4d induced cell cycle arrest in G2/M phase. Finally, 4d inhibited the migration of cancer cells in a dose-dependent manner. In summary, these results suggest that compound 4d represents a new class of tubulin inhibitors deserving further investigation.
Komuraiah, Buduma,Ren, Yichang,Xue, Mingming,Cheng, Binbin,Liu, Jin,Liu, Yao,Chen, Jianjun
p. 1109 - 1116
(2021/03/16)

HMOX1 inducers
The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.
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Page/Page column 88

(2020/09/18)

Record-high catalytic hydrogenated activity in nitroarenes reduction derived from in-situ nascent active metals enabled by constructing bimetallic phosphate
Herein, we report an excellent in-situ exsolution triggered hydrogenated catalyst F-Ni/Cu-P-RT started from bimetallic phosphate Ni/Cu-P-RT, affording an ultrafast catalytic hydrogenated rate (20 s even 5 s) in nitrophenol reduction. In the first catalytic cycle, we proved the enhanced catalytic reduction activity of bimetallic Ni/Cu-P-RT within 50 s compared to monometallic counterparts. The kinetics results revealed Ni/Cu-P-RT affords the reaction rate K of 2.85/4.23/6.6 min?1 at 20, 30, and 40 °C with the activation energy 32 kJ/mol. Impressively, the involved reaction induction period is visibly observed and interpreted by reconstruction and evolution of active metal during the reaction, but was eliminated through integrating two metal Cu-Ni by regulation of electronic band energy of phosphate from 4.1–3.5 eV. The nascent Cu and Ni nanoparticles as reaction-preferred active species were in-situ exsolved partially after adding NaBH4, triggering the resulted higher active and stable F-Ni/Cu-P-RT(20 s, 14.1 min?1) in later multiple cycles.
Yang, Fu,Wang, Jin,Gao, Shuying,Zhou, Shijian,Kong, Yan
(2020/03/10)

Hydrogenation of Substituted Benzenes Containing Nitro and Azo Groups over Skeletal Nickel in Aqueous Solutions of 2-Propanol
Abstract: An analysis is made of the kinetic characteristics of the hydrogenation of 4-nitro- and 2-nitro-2'-hydroxy-5'-methylazobenzenes, 4-nitroaniline and 4-aminoazobenzene over skeletal nickel in neutral azeotropic 2-propanol–water mixture and in the same solvent in the presence of acetic acid or sodium hydroxide. It is found that the selectivity of the hydrogenation of these isomers to the intermediate products depends on the composition and nature of the solvent, and is determined by the rate of reactive group conversion. Compared to the process in the presence of sodium hydroxide, which suppresses the route leading to the predominant hydrogenation of the nitro group, the contribution from the transformation of azo group is considerably greater in the hydrogenation of 4-nitro-2'-hydroxy-5'-methylazobenzene in the presence of acetic acid. Adding a base to the solvent during the hydrogenation of 2-nitro-2'-hydroxy-5'-methylazobenzene accelerates the rate of nitro group conversion and the intramolecular cyclization of the intermediate compound, increasing the selectivity towards the products containing the benzotriazole cycle (particularly 2-(2-hydroxy-5-methylphenyl)benzotriazole-N-oxide). The almost linear correlation between the selectivity of the catalytic hydrogenation of isomers of nitro-2'-hydroxy-5'-methylazobenzene and the kinetic characteristics of the hydrogenation of nitro and azo groups in compounds containing a single reactive substituent at different values of medium’s pH is estimated.
An’, Khoang,Belova, A. V.,Lefedova, O. V.,Nemtseva, M. P.
p. 720 - 724
(2020/04/24)

An Azo Coupling Strategy for Protein 3-Nitrotyrosine Derivatization
Herein, a strategy for the selective derivatization of 3-nitrotyrosine-containing proteins using the classic azo coupling reaction as the key step is described. This novel approach featured multiple advantages and was successfully applied to detect picomole levels of protein tyrosine nitration in biological samples.
Liu, Yuxin,Zhou, Pengcheng,Da, Honghong,Jia, Huiyi,Bai, Feifei,Hu, Guodong,Zhang, Baoxin,Fang, Jianguo
supporting information
p. 11228 - 11232
(2019/08/07)

Benzoxazole derivatives, method for preparing the same and pharmaceutical composition comprising the same
The present invention refers to benzoxazole derivatives, stereoisomers, about number cosmetically acceptable salt, solvate or hydrate number [...] substrate. (by machine translation)
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Paragraph 0194-0196

(2019/06/28)

The Continuous Synthesis of 2-(2'-Hydroxy-5'-Methylphenyl)Benzotriazole over Cu/γ-Al2O3
Abstract: The samples of 20% Cu/γ-Al2O3, 20% Co/γ-Al2O3 and 20% Ni/γ-Al2O3 were prepared as hydrogenation catalysts for continuous synthesis of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole. The best yield (86.62%) was afforded by the 20% Cu/γ-Al2O3 catalyst. The characterizations results obtained for the 20% Cu/γ-Al2O3 sample confirmed that Cu particles are evenly distributed over the surface of γ-Al2O3. A reduction of acid sites in the catalyst favored the selectivity to 2-(2'-hydroxy-5'-methylphenyl)benzotriazole. Furthermore, the effect of Cu content, reaction temperature, hydrogen pressure and liquid hourly space velocity was studied. Finally, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole in 86.62% yield was attained under the optimized conditions.
Yan,Si,Tao,Liu,Wang,Li
p. 635 - 641
(2019/10/19)

A 2 - [d] oxazole chlorobenzene and -5 - preparation of formic acid method (by machine translation)
The invention discloses a 2 - chlorobenzene and [d] oxazole - 5 - carboxylic acid, in order to 2 - nitro - 4 - methyl phenol as the starting material, passes through the reduction, ring, chlorinated, oxidation to obtain the target product, the compound is an important medical intermediates. (by machine translation)
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Paragraph 0020; 0021; 0022

(2017/12/27)

Preparation method for methylthio-substituted benzo[d]oxazole derivative
The invention discloses a preparation method for a methylthio-substituted benzo[d]oxazole derivative, i.e., 5-methyl-2-(methylthio)benzo[d]oxazole. According to the invention, 2-nitro-4-methylphenol is used as a starting raw material and undergoes reduction, ring closure and methylation so as to obtain the methylthio-substituted benzo[d]oxazole derivative. The prepared derivative is an important medical intermediate.
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Paragraph 0019; 0020

(2017/08/31)

Catalytic hydrogenation of 2-nitro-2′-hydroxy-5′-methylazobenzene over solid base-hydrogenation bifunctional catalysts: Effect of alkali metals on Pd/γ-Al2O3
Alkali metals doped Pd solid base-hydrogenation bifunctional catalysts were prepared, characterized, and employed in the hydrogenation of 2-nitro-2′-hydroxy-5′-methylazobenzene. The results indicated that the basicity of catalyst endowed by the alkali met
Si, Leilei,Wang, Bowei,Chen, Shipeng,Hou, Jingru,Yan, Xilong,Li, Yang,Chen, Ligong
p. 35 - 38
(2016/11/25)

Reductive cyclization of 2-nitro-2′-hydroxy-5′-methylazobenzene to benzotriazole over K-doped Pd/γ-Al2O3
A series of Pd/γ-Al2O3 catalysts modified by potassium salts were prepared and evaluated in the reductive cyclization of 2-nitro-2′-hydroxy-5′-methylazobenzene without additional base. These solid base-hydrogenation bifunctional catalysts were characterized and the results demonstrated that potassium salts could have an important impact on the properties and catalytic performance of Pd/γ-Al2O3.
Wang, Bowei,Si, Leilei,Yuan, Yanyan,Li, Yang,Chen, Ligong,Yan, Xilong
p. 16766 - 16771
(2016/02/20)

Redox potentials, laccase oxidation, and antilarval activities of substituted phenols
Laccases are copper-containing oxidases that are involved in sclerotization of the cuticle of mosquitoes and other insects. Oxidation of exogenous compounds by insect laccases may have the potential to produce reactive species toxic to insects. We investigated two classes of substituted phenolic compounds, halogenated di- and trihydroxybenzenes and substituted di-tert-butylphenols, on redox potential, oxidation by laccase and effects on mosquito larval growth. An inverse correlation between the oxidation potentials and laccase activity of halogenated hydroxybenzenes was found. Substituted di-tert-butylphenols however were found to impact mosquito larval growth and survival. In particular, 2,4-di-tert-butyl-6-(3-methyl-2-butenyl)phenol (15) caused greater than 98% mortality of Anopheles gambiae larvae in a concentration of 180 nM, whereas 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropanal oxime (13) and 6,8-di-tert-butyl-2,2-dimethyl-3,4-dihydro-2H-chromene (33) caused 93% and 92% mortalities in concentrations of 3.4 and 3.7 μM, respectively. Larvae treated with di-tert-butylphenolic compounds died just before pupation.
Prasain, Keshar,Nguyen, Thi D.T.,Gorman, Maureen J.,Barrigan, Lydia M.,Peng, Zeyu,Kanost, Michael R.,Syed, Lateef U.,Li, Jun,Zhu, Kun Yan,Hua, Duy H.
experimental part
p. 1679 - 1689
(2012/04/23)

Simultaneous displacement of a nitro group during coupling of diazotized o-nitroaniline with phenols
During the diazo-coupling reaction, nucleophilic displacement of a nitro group was also observed. This was the main reaction (1→7) when the starting amine bore either a chlorine or methoxy group at the para position (1b-c). The newly prepared compounds (7) might serve as convenient building blocks in synthesis of some heterocycles. Versita Warsaw and Springer-Verlag Wien 2010.
Farkas, Renata,Toerincsi, Mercedesz,Kolonits, Pal,Fekete, Jenoe,Alonso, Oscar Jimenez,Novak, Lajos
experimental part
p. 300 - 307
(2011/10/18)

NEW BENZOXAZOLE DERIVATIVE, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
The present invention relates to a new benzoxazole derivative having 5-lipoxygenase inhibitory activity, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The benzoxazole derivative according to the present invention has excellent 5-lipoxygenase inhibitory activity, reduces the degree of airway hypersensitivity, levels of cytokines IL-4, IL-5, and IL- 13, Ova-specific IgE in serum, and degree of the peribronchial and perivascular inflammation, statistically significantly reduces the number of TRAP(+) MNCs, and significantly inhibits osteoclastogenesis in a co-culture system of bone marrow cells and osteoblasts, thereby being used to prevent and treat diseases induced by leukotriene, in particular, inflammatory diseases including asthma or osteoporosis.
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Page/Page column 6

(2008/06/13)

Regulatory molecules for the 5-HT3 receptor ion channel gating system
Substituted benzoxazole derivatives which possess a nitrogen-containing heterocycle at C2 are selective partial agonists of the 5-HT3 receptor. Alteration of substituents on the benzoxazole nucleus affords both agonist-like and antagonist-like compounds, and uniquely modifies the function of the 5-HT3 receptor ion channel gating system. SAR and corroborative computational docking study for these partial agonists successfully explained structure and function of the 5-HT3 receptor.
Yoshida, Satoshi,Watanabe, Takashi,Sato, Yasuo
p. 3515 - 3523
(2008/02/07)

Ramoplanin derivatives possessing antibacterial activity
Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.
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Page/Page column 68

(2010/11/23)

Microwave assisted synthesis of 4-alkyl-2-([5-substituted-2-hydroxyphenyl]- iminomethyl)benzenols and their NMR characterization
Imines, 4-alkyl-2-([5-substituted-2-hydroxyphenyl]iminomethyl)-benzenols 1, have been obtained successfully in excellent yield from the corresponding aldehydes and amines by microwave irradiation. The resultant Schiff bases have been fully characterized by spectral data.
Sridharan,Muthusubramanian,Sivasubramanian
p. 416 - 419
(2007/10/03)

Reduction of nitrophenols by zinc and ammonium chloride in aqueous medium
A simple reduction procedure involving zinc and ammonium chloride in aqueous medium has been employed for the reduction of nitrophenols to aminophenols.
Sridharan,Karpagavalli,Muthusubramanian,Sivasubramanian
p. 2243 - 2244
(2007/10/03)

Bisacetamide hydrochloride: A chemoselective and inexpensive N-acetylating reagent for aminophenols
A facile and chemoselective acetylation of aminophenols using bisacetamide hydrochloride under conventional heating and microwave irradiation has been developed. Also, a rapid method for the microwave-assisted preparation of aminophenols is described herein.
Peng, Yanqing,Song, Gonghua,Ding, Fang
p. 2021 - 2023
(2007/10/03)

Liquid-phase hydrogenation of 2-nitro-2′-hydroxy-5′- methylazobenzene on raney nickel at low temperatures
The character of changes in the concentrations of intermediate products at the initial stage of the hydrogenation of 2-nitro-2′-hydroxy-5′- methylazobenzene (I) on Raney nickel at 275 K and the reasons for their dependence on the composition of the solvent were determined. The smallest amount of I and the largest yield of substituted benzotriazole N-oxide were obtained when the reaction was conducted in a 2-propanol-water solvent containing sodium hydroxide. Conversely, the addition of acids to the solvent sharply increased the yield of the nitrohydrazo derivative. The selectivity of hydrogenation with respect to the substituted benzotriazole was determined by the ratio between the rates of hydrogenation of the nitro and azo groups in the initial compound and intramolecular homogeneous rearrangements of intermediate products.
Zuenko,Nemtseva,Lefedova,Nikolaev
p. 877 - 881
(2007/10/03)

Hydrogenation kinetics of 2′-hydroxy-5′ -methyl-2-nitroazobenzene under quasisteady conditions
The kinetics of the liquid-phase hydrogenation of 2′-hydroxy-5′ -methyl-2-nitroazobenzene on skeletal nickel in propan-2-ol and its mixtures with water and sodium hydroxide was studied under quasisteady conditions ensured by a measured substrate feed into a reaction vessel. 2-(2-Hydroxy-5-methylphenyl)benzotriazole N-oxide, 2′-hydroxy-5′ -methyl-2-nitrohydrazobenzene, and aromatic amines were found to be the major reaction intermediates under both steady and quasi-steady conditions, provided the compositions of the solvents are the same. The highest reaction selectivity for the target product, namely, 2-(2-hydroxy-5-methylphenyl)benzotriazole, can be reached at low concentrations of the starting reagent in a chemisorbed layer and high rates of cyclization of 2′-hydroxy-5′ -methyl-2-nitrohydrazobenzene into 2-(2-hydroxy-5-methylphenyl)benzotriazole N-oxide.
Lefedova
p. 1266 - 1269
(2007/10/03)

A new intramolecular migration of the imino group of O-arylketoximes to the aryl group under the Beckmann condition
ZrCl4-mediated decomposition of O-arylketoximes in benzene leads to regioselective intramolecular migration of the imino group from the oxygen to the ortho position of the aryl group via electron-deficient nitrogen intermediates.
Kikugawa, Yasuo,Tsuji, Chiho,Miyazawa, Etsuko,Sakamoto, Takeshi
p. 2337 - 2339
(2007/10/03)

2-bromo-2-nitropropane/zn promoted reductive cyclizations of ortho-carbonyl, imino, or azo substituted nitrobenzenes
Under the mild conditions, reductive cyclizations of 2-nitrobenzaldehydes, 2'-nitroacetophenone, and N-(2-nitrobenzylidene)anilines were accomplished in the presence of 2-bromo-2-nitropropane/Zn in methanolic solution. Under the similar conditions in MeOH/CH2Cl2, o-nitro-substituted phenylazobenzenes have been converted into 2-aryl-2H-benzotriazoles via reductive cyclizations that are widely used as UV absorbers. Synthesis and mechanistic details are discussed.
Kim, Byeong Hyo,Lee, Yoon Seok,Kwon, Woong,Jin, Youngoo,Tak, Jung Ae,Jun, Young Moo,Baik, Woonphil,Lee, Byung Min
p. 2581 - 2592
(2007/10/03)

N-tert-butoxycarbonyl (BOC) deprotection using boron trifluoride etherate
A mild and efficient procedure is described for the removal of the tert- butoxycarbonyl (BOC) group using boron trifluoride etherate and molecular sieves in dichloromethane at room temperature. The scope of this procedure is explored for the deprotection of a variety of amines including amino acid derivatives.
Evans, Emily F.,Lewis, Norman J.,Kapfer, Isabelle,Macdonald, Gregor,Taylor, Richard J. K.
p. 1819 - 1825
(2007/10/03)

Novel biocatalytic reduction of aryl azides: Chemoenzymatic synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics
The chemoselective reduction of aryl azides to aryl amines, and the synthesis of the imine-containing pyrrolo[2,1-c][1-4]benzodiazepine DNA-binding antitumour antibiotics by selective biocatalytic reductive cyclization of azido aldehydes, has been achieved by employing baker's yeast.
Kamal, Ahmed,Damayanthi,Reddy, B. S. Narayan,Lakminarayana,Reddy, B. S. Praveen
p. 1015 - 1016
(2007/10/03)

Fiber reactive anthraquinone dyes
The invention is that of a water soluble fiber reactive anthraquinone blue dyes. These dyes may be used to dye and print textiles and other substrates containing hydroxy and or groups in brilliant blue colors. The dyes of the invention are free of heavy metals.
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(2008/06/13)

Acid-catalyzed amino-migration of O-phenylhydroxylamines
The mechanism of amino-migration of O-phenylhydroxylamine (1a) was studied. It was found that 1 rearranges to give 2-aminophenol (50%) and 4-aminophenol (7%) in trifluoroacetic acid (TFA). The predominance of the ortho rearrangement of 1 clearly distinguishes this process from the Bamberger rearrangement. From cross-coupling experiments employing stable isotopes, it was clarified that the ortho rearrangement proceeds intramolecularly and the para rearrangement involves both intra- and intermolecular processes. Good first-order kinetics were obtained for the rearrangement. The Hammett plot (σ+) with a large negative slope (ρ = -7.8) indicates that initial heterolytic N-O bond cleavage of 1 occurs and generates a positive charge on the oxygen atom with considerable delocalization into the aromatic ring. An ion-molecule pair involving a phenoxenium ion and an ammonia molecule as an intermediate rationalizes all of the results. In this pair, intramolecular combination to the ortho position proceeds preferentially over that to the para position. Formation of catechol and hydroquinone can be explained in terms of nucleophilic attack of TFA on the phenoxenium ion in a solvent-separated pair.
Haga, Naoki,Endo, Yasuyuki,Kataoka, Ken-Ichiro,Yamaguchi, Kentaro,Shudo, Koichi
p. 9795 - 9806
(2007/10/02)

Synthesis, Spectral Data and Extraction of Copper by 1-(2'-Hydroxy-5'-alkylphenyl)-1-alkanone Oximes
1-(2'-Hydroxy-5'-alkylphenyl)-1-ethanone oximes with a normal alkyl group containing 2 to 12 carbon atoms and 1-(2'-hydroxy-5'-methylphenyl)-1-alkanone oximes containing 1 to 11 carbon atoms in the hydrocarbon chain were synthesized.Spectral data (u.v., i.r., n.m.r. and 13C) of oximes are reported.Four of these oximes were used for copper extraction from acidic solution.The results obtained indicate, that these oximes are better extractants than alkyl derivatives of 2-hydroxybenzophenone oximes.
Krzyzanowska, Ewa,Olszanowski, A.,Juskowiak, M.
p. 617 - 630
(2007/10/02)

Electrochemical Reduction of Nitroaromatics to Anilines in Basic Media: Effects of Positional Isomerism and Cathode Composition
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Stutts, K. J.,Scortichini, C. L.,Repucci, C. M.
p. 3740 - 3744
(2007/10/02)

Reaction of Triphenylphosphine with Copper Complexes derived from 2-Nitrosophenols (1,2-Quinone Mono-oximes)
Reaction of triphenylphosphine with the copper(II) complexes of 5-methoxy-2-nitrosophenol, 4-methyl-2-nitrosophenol, 1-nitroso-2-naphthol, and 2-nitroso-1-naphthol involves deoxygenation of one of the ligands to give 2-amino-7-methoxy-3H-phenoxazin-3-one, 4-methyl-2-aminophenol, 1-amino-2-naphthol, and 2-amino-N4-(1-hydroxy-2-naphthyl)-1,4-naphthoquinone 4-imine respectively as the major organic products.In all cases reduction of the metal occurs to give a complex of type Cu(qo)(PPh3)2 (qoH = nitrosophenol).The reactions are rationalised in terms of nitrene intermediacy.An X-ray diffraction study of Cu(qo)(PPh3)2 (qoH = 1-nitroso-2-naphthol) has been undertaken.
Buckley, Robert G.,Charalambous, John,Kensett, Malcolm J.,McPartlin, Mary,Mukerjee, Deepak,et al.
p. 693 - 697
(2007/10/02)

Interaction of Copper Complexes Derived from 1,2-Quinone Monooximes(2-Nitroso-phenols) with Amines
The reactions of 1,2-diaminoethane with the copper(II) complexes of 4-methyl- and 5-methoxy-1,2-benzoquinone 2-oxime involve deoxygenation of the ligand and reduction of the metal, and lead to 2-amino-4-methylphenol and 2-amino-7-methoxy-3H-phenoxazin-3-one, respectively.Reactions of the copper(II) complex of 1,2-naphthoquinone 2-oxime with 1,2-diaminoethane and with aniline occur in an analogous fashion, and lead to dibenzophenazine-5,12-diol and 2-amino-1,4-naphthoquinone 4-N-phenylimine, respectively.The copper(II) complex of 1,2-naphthoquinone 1-oxime reacts with aniline to give bis(1,4-dihydro-1-imino-4-phenylimino-2-naphtholato)bis(aniline)copper(II) and with 1,2-diaminoethane to give a complex mixture of products.The reactions are rationalized in terms of nitrene intermediacy.
Buckley, Robert G.,Charalambous, John,Brain, Edward G.
p. 1075 - 1078
(2007/10/02)

On the Structure of Thiazolylazo-Oxines and their Behaviour in Forming of Complexes
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Roebisch, G.,Friedemann, W.,Gruendemann, E.
p. 979 - 984
(2007/10/02)

2-STYRYLBENZOXAZOLE DERIVATIVES
A series of 35 derivatives of 2-styrylbenzoxazole I-XXXV with methyl, chloro, hydroxy, methoxy, dimethylamino, nitro, cyano and methoxycarbonyl substituents have been prepared by reaction of substituted 2-acetamidophenol with respective benzaldehyde derivatives.
Arient, Josef
p. 3160 - 3165
(2007/10/02)

Pyridopyrrolobenzoxazine
Compounds of the formula: STR1 where 2 THE R's are the same or different and are H or CH3, and one of them can be C2 -C9 alkyl or phenyl; R1 is hydrogen, C1 -C4 alkyl, C3 -C6 cycloalkyl, C2l -C4 alkoxycarbonyl, or substituted C1 -C4 alkyl where the substituent is C3 -C6 cycloalkyl or phenyl; and Z is H, Cl or CH3 ; and their pharmaceutically suitable salts. The compounds are useful as sedatives; some of them also exhibit antidepressant activity.
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(2008/06/13)