- Synthesis and antimicrobial activities of some novel thiophene containing azo compounds
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A series of new thienylazothiophenes were prepared by coupling reactions of diazotized thienocoumarins with their corresponding free amines. The structures of the products 3-7 were assigned on the basis of their elemental and spectroscopic data. The HMBC and HSQC techniques were used in some cases to ascertain the structural assignments. The antimicrobial screenings of compounds 3-7 along with substituted 2-aminothiophenes 1a,b were performed against three bacteria and three fungal species and their activities compared to those of nystatin, gentamycin and ciprofloxacin used as reference drugs. It was found that the antimicrobial activities of the tested new hybrid compounds were in some cases equal or better than those of the reference drugs.
- Fondjo, Emmanuel Sopbue,Tsemeugne, Joseph,De Dieu Tamokou, Jean,Djintchui, Arnaud Ngongang,Kuiate, Jules Roger,Sondengam, Beibam Luc
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- Chemiluminescence properties of isoluminol related mono azo disperse dyes: Experimental and DFT based approach to photophysical properties
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A six novel isoluminol derivatives containing azo unit were synthesized by coupling different N,N-disubstituted anilines with the diazotized 5-nitro and 7-nitro-6-amino-2,3-dihydrophthalazine-1,4-dione. The chemiluminescent properties were studied in hydrogen peroxide, potassium hexacyanoferrate(III) and sodium hydroxide solution. The chemiluminescence properties were compared with the standard isoluminol systems it was observed that the chemiluminescence properties of the novel derivatives were nearly same to isoluminol. The geometries of the synthesized disperse dyes for their azo and hydrazone tautomeric forms were optimized using density functional theory and their electronic excitation properties were evaluated using density functional theory and time dependent density functional theory.
- Deshmukh, Mininath S.,Sekar, Nagaiyan
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- A combined experimental and DFT investigation of mono azo thiobarbituric acid based chalcone disperse dyes
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A number of monoazo dyes were synthesized by the reaction of 4-aminoacetophenone with different substituted benzaldehydes to give a new series of chalcone derivatives. The diazonium salts of these chalcones then allowed to react with thiobarbituric acid to produce the appropriate azo dye. The structures of the newly synthesized dyes were assigned by IR, NMR spectral data. IR study confirmed the existence of azo-dioxothioxo tautomer in the solid phase while 1H NMR study indicated the predominance of azoenol-oxothioxo or hydrazo-dioxothioxo tautomers. The geometries of the azo and hydrazo tautomeric forms and their electronic absorption of the dyes were optimized at B3LYP/6-311G level of theory. All the azo compounds were evaluated for their dyeing performance on polyester fibers, and PET. All the synthesized dyes gave moderate to excellent fastness properties on PET fiber. The effects of the nature of the substituents on the color and dyeing properties of these dyes have been evaluated. The mechanism of dyeing polyester fiber was discussed.
- El-Sadany, Samir K.,El-atawy, Mohamed A.,Hamed, Ezzat A.,Mahmoud, Mona N.,Omar, Alaa Z.
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- Synthesis, characterization, pharmacological evaluation and molecular docking studies of benzothiazole azo derivatives
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A series of novel benzothiazole based azo dyes were synthesized and fully characterized by using different analytical techniques. The antioxidant activity of synthesized azo dyes was studied with the DPPH, hydrogen peroxide, metal chelating and nitric oxide radical methods and compared with the known antioxidant ascorbic acid. Further, the anticancer properties of synthesized azo dyes were carried out against breast cancer (MCF-7) cell lines by MTT assay and results revealed that the synthesized compounds exhibited good anticancer property in micro-molar range. Additionally, the anti-inflammatory activities of target compounds were also investigated by protein denaturation method and were found to have effective anti-inflammatory property. In order to predict the binding modes and binding affinity of synthesized compounds, they were docked into the active sites of protein B-cell lymphoma-extra-large (Bcl-xL) to predict their anticancer property. The synthesized compounds were found to have good affinity for B-cell lymphoma-extra-large (Bcl-xL). A good correlation was found between in-silico docking analysis and in biological screening of all synthesized azo dyes with less binding energies and higher inhibition constants value against the target protein.
- Harisha,Keshavayya, Jathi,Prasanna,Joy Hoskeri
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- On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid
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The reaction of 2-benzylamino-1,4-naphthoquinone with nitrosylsulfuric acid in acetic acid results in preferential formation of 2,1- and 2,3-heterocyclization products: (E)-4-(hydroxyimino)-2-phenylnaphtho [2,1-d]oxazol-5(4H)-one and 2-phenyl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-dione. In addition, 2-phenylnaphtho[2,1-d]oxazol-4,5-dione and N-(3-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide are also formed. The reaction of 2-benzylamino-3-chloro-1,4-naphthoquinone with nitrosylsulfuric acid in acetic acid gives 3-diazonapthalene-1,2,4(3H)-trione and benzaldehyde.
- Gornostaev,Nuretdinova,Lavrikova,Khalyavina, Yu. G.,Fominykh,Gatilov, Yu. V.
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p. 608 - 614
(2019/07/17)
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- Anhydrous Dinitrogen Trioxide Solutions for Br?nsted Acid Free Nitrous Acid Chemistry
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Dinitrogen trioxide, N2O3, is readily prepared and stabilized in high concentrations in dry organic solvents at normal working temperatures. These conditions allow for facile acid and water free nitrosation and nitration reactions fo
- Rosadiuk, Kristopher A.,Bohle, D. Scott
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p. 5461 - 5465
(2017/12/26)
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- Synthesis and absorption abilities of pyrazolo[5,1-c][1,2,4]triazine-based disperse dyes
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A series of 13 novel pyrazolo[5,1-c][1,2,4]triazine-based disperse dyes was synthesized by heating ethyl pyrazolylhydrazonocyanoacetate in glacial acetic acid. Solvent and acid-base influences on the wavelength of maximum absorption have been studied.
- Karc?,Karci
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p. 457 - 465
(2013/07/26)
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- Etching silicon with HF-HNO3-H2SO4/H 2O mixtures- unprecedented formation of trifluorosilane, hexafluorodisiloxane, and Si-F surface groups
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The etching behaviour of sulfuric-acid-containing HF-HNO3 solutions towards crystalline silicon surfaces has been studied over a wide range of H2SO4 concentrations. For mixtures with low sulfuric acid concentration, NO2/N2O4, N 2O3, NO and N2O have been detected by means of FTIR spectroscopy. Increasing concentrations of nitric acid lead to high etching rates and to an enhanced formation of NO2/N2O 4. Different products were observed for the etching of silicon with sulfuric-acid-rich mixtures [c(H2SO4) > 13 mol L -1]. Trifluorosilane and hexafluorodisiloxane were identified by FTIR spectroscopy as additional reaction products. In contrast to the commonly accepted wet chemical etching mechanism, the formation of trifluorosilane is not accompanied by the formation of molecular hydrogen (according to Raman spectroscopy). Thermodynamic calculations and direct reactions of F 3SiH with the etching solution support an intermediate oxidation of trifluorosilane and the formation of hexafluorodisiloxane. The etched silicon surfaces were investigated by diffuse reflection FTIR and X-ray photoelectron spectroscopy (XPS). Surprisingly, no SiH terminations were observed after etching in sulfuric-acid-rich mixtures. Instead, a fluorine-terminated surface was found.
- Lippold, Marcus,Boehme, Uwe,Gondek, Christoph,Kronstein, Martin,Patzig-Klein, Sebastian,Weser, Martin,Kroke, Edwin
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p. 5714 - 5721
(2013/02/25)
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- Azo compounds and coating compositions containing the azo compounds
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Disclosed are azo colorant compounds containing one or more ethylenically-unsaturated groups polymerizable or copolymerizable with ethylenically-unsaturated compositions typically used in coating compositions. The azo colorantcompounds are polymerizable by photopolymerization or free radical polymerization techniques with ethylenically-unsaturated monomers. The copolymerized colorants produce colored compositions such as colored acrylic polymers, e.g., polymers produced from acrylate and methacrylate esters, colored polystyrenes, and similar colored polymeric materials derived from other ethylenically-unsaturated monomers. The ethylenically-unsaturated colorant compounds may be used in coatings that are applied to wood, glass, metal, thermoplastics and the like.
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- Dye composition
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The invention provides a dye composition for dyeing fibers comprising (a) an azo dye of formula (II) or a salt thereof, and (b) an azo dye of formula (III) or a salt thereof. The invention provides navy and black dye compositions, especially suitable for dyeing secondary cellulose acetate fibers, with superior fastness properties than known navy/black dyes. Preferably, the α-crystal form of dye (III) is used, which has greater solubility and achieves quicker dyeing than the commonly-used β and γ forms of (III) when dyeing cellulose acetate at 60-95° C. A new method of making the α form is disclosed.
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- 1, 2-dihydro-3H-dibenzisoquinoline-1,3-dione anticancer agents
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This invention relates to a compound useful for the treatment of tumors having the formula: STR1
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- Pesticidal method using 2-phenylimidazole derivatives
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The invention provides a method for the control of arthropod, plant nematode, helminth or protozoan pests using a 2-phenylimidazole derivative of the formula: STR1 wherein R1 represents hydrogen, alkyl (optionally substituted by alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxy or alkoxycarbonyl), R2 and R3, each represents hydrogen, halogen, nitro, carboxy, cyano, alkoxycarbonyl, alkanoyl, or optionally alkyl substituted carbamoyl or sulphamoyl, or amino (optionally substituted by alkyl, alkoxycarbonyl or alkanoyl) or a group R, RO, RS, RSO or RSO2 in which R represents alkyl (optionally substituted by halogen), and Ar represents a group of the formula: STR2 wherein R4 and R6 each represents halogen or a group R, RO, RS, RSO or RSO2, and R5, R7 and R8 each represents a substituent as defined for R4 and R6, or represents hydrogen, hydroxy, carboxy, nitro, cyano, amino, alkylamino (optionally substituted by alkyl, alkoxycarbonyl or alkanoyl), alkoxycarbonyl or alkanoyl or a pesticidally acceptable salt thereof, with the exclusion of compounds in which R2 and R3 simultaneously represent hydrogen atoms, compositions for use in the method and novel compounds of formula I.
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- Electro-optical materials and light modulator devices containing same
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Azo-type optically active compounds and polymers are provided based on compounds of the general structure wherein aryl substituents are introduced which hinder or prohibit rotation around the single bonds of the --N=-- central moiety (as well as around certain other single bonds), to provide "planarized" structures having improved optically active properties, especially electro-optically active properties. These compounds and polymers find use in optically active waveguides.
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- Derivatives of N-phenylpyrazoles
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N-Phenylpyrazole derivatives of the formula: STR1 wherein R1 represents cyano, nitro, halogen, acetyl or formyl; R2 represents R5 SO2, R5 SO or R5 S in which R5 is optionally halogen substituted alkyl, alkenyl or alkynyl; R3 represents a hydrogen atom or a group NR6 R7 wherein R6 and R7 each represent hydrogen, alkyl, alkenylalkyl, alkynylalkyl, formyl, optionally halogen substituted alkanoyl, optionally halogen substituted alkoxycarbonyl, or alkoxymethyleneamino, halogen, or R6 and R7 together form a cyclic imide and R4 represents a substituted phenyl group possess arthropodicidal, plant nematocidal, anthelmintic and anti-protozoal properties; their preparation, compositions containing them and their use are described.
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- Azo dyes containing 5-cyclohexylcarbonyl-thiophene diazo components and 1,2,3,4-tetrahydroquinoline coupling components
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The azo dyes of the formula STR1 in which R1 is hydrogen or substituted or unsubstituted C1 -C10 alkyl, R2 is a group of the formula, --CN, --CON(R8)R9, --COR10, --COOR11, --SO2 R12 or --CONHNHR13, R3 is hydrogen, halogen, C1 -C4 alkyl, C2 -C6 alkanoylamino, C1 -C10 alkoxy or phenoxy, R4 is substituted or unsubstituted C1 -C10 alkyl, R5 is C1 -C4 alkyl, R6 is hydrogen or C1 -C4 alkyl, R7 is hydrogen or C1 -C4 alkyl, R8, R9 and R13, independently of one another, are hydrogen or substituted or unsubstituted C1 -C10 alkyl, C5 -C7 cycloalkyl, phenyl or naphthyl, R10, R11 and R12 are substituted or unsubstituted C1 -C10 alkyl, C5 -C7 cycloalkyl, phenyl or naphthyl, X is an oxygen atom or a group of the formula --CH(R14)-- in which R14 is hydrogen or C1 -C4 alkyl, Y is a water-solubilizing group, n is the number 1 or 2 and m is the number 1 or 2, produce on nitrogen-containing or hydroxyl-containing fibre materials dyeings having good fastness properties.
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- Aromatic disazo compounds having strong infra-red absorption
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An azo compound of the formula: wherein: A is (i) a phenyl group containing at least two unsaturated electron-withdrawing groups in ortho or para positions with respect to the azo link, (ii) an aromatic heterocycle, or (iii) the residue of an aromatic coupling component having a group displaceable by a diazotized aromatic amine; B is an substituted or unsubstituted thien-2,5-ylene or thiazol-2,5-ylene group; and D is the residue of an aromatic coupling component having a group displaceable by a diazotized aromatic amine. The azo compound has a significant absorption band extending into the near infra-red region of the spectrum and has utility in applications, such as solar screening, electronic, optical character recognition, printing, reprographic and security systems, where enhanced infra-red absorption is necessary or desirable.
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- Derivatives of N-phenylpyrazoles, compositions and use
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An N-phenylpyrazole derivative of the formula: STR1 wherein R1 represents cyano, nitro or halogen; R2 represents a group R5 SO2, R5 SO, or R5 S in which R5 represents alkyl, alkenyl or alkynyl unsubstituted or substituted by halogen; R3 represents azido or hydrazino, or pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,4-triazol-4-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, piperidino, pyrrolidino, morpholino or N-alkylpiperazino, which may be substituted by alkyl or phenyl; and R4 represents phenyl substituted in the 2-position by fluorine, chlorine, bromine or iodine; in the 4-position by alkyl or alkoxy unsubstituted or substituted by halogen, or fluorine, chlorine, bromine or iodine; and unsubstituted or substituted in the 6-position by fluorine, chlorine, bromine or iodine and pesticidally acceptable acid addition salts thereof possess arthropodicidal, nematocidal, anthelmintic and anti-protozoal activity.
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- Gamma-Glutamyl-4-azoanilides
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The present invention provides gamma-glutamyl-4-azoanilides, processes for their preparation and their use as substrates for gamma-glutamyl transferase determination, of the formula STR1 wherein X is alkyl, --(CH2)m --COOH or --O--(CH2)n --COOH wherein m is 0-4 and n is 1-4; R is optionally substituted p-nitrophenyl; an optionally substituted thiophene residue; an optionally substituted thiazole residue; an optionally substituted benzothiazole residue; an optionally substituted benzoisothiazole residue; an N-alkylthiazole residue; or an optionally substituted 1,3,5-thiodiazole residue; as well as the alkali metal, alkaline earth metal and ammonium salts thereof.
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- 4-alkyl-2-trifluoromethylanilines
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4-Alkyl-2-trifluoromethylanilines, in particular the 4-isopropyl derivative, are starting materials for preparing valuable azo dyestuffs. While the nonionic dyestuff types can preferably be used in transfer printing synthetic hydrophobic fibre materials, the sulpho-containing dyestuffs--in particular those based on "gamma acid"--are suitable for dyeing polyamides.
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- Derivatives of N-phenylpyrazoles
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N-Phenylpyrazole derivatives of the formula: wherein R1 represents cyano, nitro, halogen, acetyl or formyl:, R2 represents R5SO2, R5SO or R5S in which R5 is optionally halogen substituted alkyl, alkenyl or alkynyl;, R3 represents a hydrogen atom or a group NR6R7 wherein R6 and R7 each represent hydrogen, alkyl, alkenylalkyl, alkynylalkyl, formyl, optionally halogen substituted alkanoyl, optionally halogen substituted alkoxycarbonyl, or alkoxymethyleneamino, halogen, or R6 and R7 together form a cyclic imide and R4 represents a substituted phenyl group possess arthropodicidal, plant nematocidal, anthelmintic and anti-protozoal properties; their preparation, compositions containing them and their use are described.
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- 5-C1-4 alkoxy-2-C1-2 alkyl-2',4'-dinitro-6'-halo-4-substituted amino-azobenzenes
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Compounds of the formula STR1 wherein R1 is nitro or cyano; R2 is cyano or halo; R3 is C1-4 alkyl; R4 is methyl or ethyl; R5 is C1-8 alkyl; and R6 is --CH2 CHOHCH2 O(CH2 CH2 O)a R7, --CH2 CHOHC6 H5, --CH(C6 H5)CH2 OH; --(CH2)n O--CO--NHR3, --CH2 CH(R4)--O--CO--NHR3 ; --(CH2)n --O--CO--R3, --CH2 CH(R4)--O--CO--R3 or C2-4 hydroxyalkyl, with the provisos that R6 may be any of the last three groups only when R1 and R2 are both cyano and that R6 may be C2-4 hydroxyalkyl also when R5 is C1-2 alkyl, wherein R7 is phenyl; phenyl substituted by 1 or 2 substituents independently selected from hydroxy, chloro, bromo, methyl and C1-4 alkoxy; benzyl; benzyl substituted by 1 or 2 substituents independently selected from hydroxy, chloro, bromo, methyl and C1-4 alkoxy; allyl; haloalkyl; propyn-2-yl or halopropyn-2-yl, with the proviso that R7 may be allyl, haloallyl, propyn-2-yl or halopropyn-2-yl only when a is 0; a is 0 or 1; and n is 2 or 3, processes for their preparation and their use for dyeing and printing textiles comprising synthetic or semi-synthetic, hydrophobic, high molecular weight materials, e.g., linear aromatic polyester, cellulose 21/2 acetate, cellulose triacetate and synthetic polyamides, by, for example, the rapid dyeing procedure.
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- Process for preparing azo dyes
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Disclosed is a process for coupling a disperse dye diazo component selected from diazonium salts of substituted and unsubstituted phenyl, 2-thiazolyl, 2-benzothiazolyl, 1,3,4-thiadiazol-2-yl, 1,2,4-thiadiazol-5-yl, 2,1-benzisothiazol-3-yl, isothiazol-5-yl, 1,3,4-triazol-2-yl, pyrazol-5-yl, imidazol-2-yl, phthalimid-3 or 4-yl, 1-naphthyl, and 2-thienyl radicals comprising reacting with said component a disperse dye coupler having in the coupling position on the ring a substituent typified by --CHO, --COOH, --COCH3, --SO3 H, displaceable diazonium radicals including the above, and another or the same coupler linked to said coupler by certain bivalent radicals.
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- Azo dyes from five membered ring heterocyclic amines and aniline, tetrahydroquinoline and benzomorpholine couplers containing thiosulfate alkyl groups
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Disclosed are mono azo dyes derived from diazotized 5-membered heterocyclic amines and certain aniline, 1,2,3,4-tetrahydroquinoline, and benzomorpholine couplers containing thiosulfate alkyl groups. These dyes are useful for dyeing synthetic fibers, cellulose acetate and wool, and particularly impart fast violet to blue shades on polyamide fibers, and in general, exhibit improved properties such as fastness to light, sublimation, ozone, oxides of nitrogen, perspiration, crock, and wash, and exhibit excellent build, pH stability, bloom resistance, depth of shade, leveling, migration, and the like. The dyes have the general formula: wherein D is a thiadiazol, isothiazol, pyrazol or thiophene type radical, and the Coupler is an aniline, tetrahydroquinoline, or benzomorpholine derivative wherein a --ZSSO3 M group is attached to the nitrogen thereof, the coupler ring may contain substituents such as alkyl, alkoxy, halogen, acylamido, alkylthio or aryloxy, the remaining hydrogen of the aniline coupler may be replaced by a substituent such as alkyl, substituted alkyl, alkenyl, aryl, or cycloalkyl, M is Na+, K+, NH4+ or H+, and Z is a linking group such as ethylene.
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- Azomethine dyes derived from an o-hydroxy aromatic aldehyde and a 2-aminopyridine
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Azomethine dyes of the formula STR1 in which A is phenyl, naphthyl, phenyl substituted by up to 3 substituents or naphthyl substituted by up to 2 substituents; B is salicylaldehyde, o-hydroxy-naphthaldehyde or salicylaldehyde or o-hydroxy-naphthaldehyde substituted by up to 2 substituents and C is 2-aminopyridyl or 2-aminopyridyl substituted by up to 2 substituents. The dyes produce dyeings on metal-modified polypropylene of excellent fastness properties.
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- Chelatable triazolylazo-N-alkyl(cycloalkyl)acylacetamide dyes
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Disclosed are novel triazolylazo-N-alkyl(cycloalkyl)acylacetamide dye compounds which are colorless in solution but develop a yellow color when treated with ionic nickel such as nickel salts of organic acids or cobalt salts. This property is useful in conventional dyeing procedures and in reprographic processes wherein the dye compound is in hydrocarbon media when development of the color occurs.
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