- Coupling reactions of diazonium betaines with alkyl dicyanoacetates
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The reactions of heterocyclic diazonium betaines, 4-aryl-3-diazo-pyrazole and 3-diazo-indazole, at the α-carbon atoms of alkyl dicyanoacetates gave corresponding azo-compounds.
- Neidlein,Sui
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Read Online
- COMPOUNDS HAVING PSEUDOMONAS ANTI-BIOFILM PROPERTIES
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The present invention relates to c-di-GMP lowering chemical compounds having anti- biofilm properties. In particular, the present invention relates to anti-biofilm compounds or salts or tautomers thereof for use in treatment and/or prevention of bacterial biofilm infection in human subjects caused by biofilm-forming bacteria of the genus Pseudomonas, in particular Pseudomonas spp. including P. aeruginosa. Methods of treating such infections in human subjects are contemplated as well. The present inventions further relates to the use of an anti-biofilm compound or a salt or tautomer thereof for dispersing biofilms in industrial water systems.
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Page/Page column 27; 24
(2022/03/09)
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- Synthesis of arylhydrazone-based molecular switches using aryldiazonium silica sulfate nanocomposites and analysis of their isomerization
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A fast and efficient method for the synthesis of a series of arylhydrazones by reacting aryldiazonium silica sulfate nanocomposites with malononitrile, ethyl acetoacetate and dimedone is reported. All reactions were carried out in water at room temperature and the corresponding products were obtained in 77–87% yields. The existence of two kinds of intramolecular hydrogen bonds in the arylhydrazones synthesized using ethyl acetoacetate enables these compounds to be switched by rotation about the hydrazone C[dbnd]N bond, which leads to a reversible isomerization between their E and Z configurations. This switching can be controlled by changing the polarity of the solvents. The E/Z ratio of each synthesized compound was studied in CHCl3 and DMSO. The ratios of the E/Z were calculated using 1H NMR data in both CDCl3 and DMSO?d6, and used to calculate ΔG° for the E-Z isomerization of each synthesized compound in these two solvents. By changing the solvent from CHCl3 to DMSO, the E/Z ratios decreased. The results demonstrated that the ΔG° values for the formation of Z isomers were more negative than those of the E isomers in DMSO. This is why Z isomers are more stable than E isomers in DMSO. The results of density functional theory (DFT) calculations at B3LYP/6–311++G (d,p) level of theory, were in agreement with the experiments and confirmed the increased stability of Z isomers in DMSO. In most cases, DFT calculation in CDCl3 and DMSO indicate that the dipole moments of the Z isomers are significantly higher than those of the E isomers. Finally, the effect of temperature on the E-Z isomerization was studied using dynamic 1H NMR. The findings demonstrated that temperature does not have any significant effect on the E-Z isomerization in CDCl3 and DMSO?d6.
- Abbaspourrad, Alireza,Aghaei, Hamidreza,Chermahini, Alireza Najafi,Khazdooz, Leila,Soltani, Solmaz,Zarei, Amin
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- Novel heterocyclic disazo dyes containing pyrazole and phenylpyrazole. part 1: Synthesis, characterization, solvent polarity and acid-base sensitive characteristics
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A series of diazotised aniline and aniline derivative compounds were reacted with solution of malononitrile in pyridine at 0–5 °C were obtained 1a-1m compounds. Then 4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by coupling arylazo malononitrile compounds with hydrazine. Finally, the synthesized pyrazole derivative 2a-2m compounds were again diazotised. By reacting these diazotised compounds with 3-amino-5?hydroxy-1-phenylpyrazole, the new thirteen heterocyclic disazo dyes (3a-3m) were joined the dye literature and the dye industry. The structures of these newly synthesized compounds were characterized using elemental analysis and spectroscopic methods such as Fourier transform infrared spectroscopy-Attenuated total reflectance (FT-IR-ATR), 1H-Nuclear magnetic resonance (1H NMR) spectroscopy and mass spectroscopy. Then solvatochromic properties and solvent effect in dimethyl sulfoxide, dimethyl formamide, acetonitrile, acetic acid, methanol and chloroform were investigated. In addition, the effects of organic and inorganic acids and bases on the absorption spectra of the compounds and the substituent effect of the phenyl ring-bound groups were investigated.
- Demir?al?, Aykut
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- SAR study of 4-arylazo-3,5-diamino-1: H -pyrazoles: identification of small molecules that induce dispersal of Pseudomonas aeruginosa biofilms
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By screening of a collection of 50 000 small-molecule compounds, we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of anti-biofilm agents. Here, we report a SAR study based on 60 analogues by examining ways in which the pharmacoph
- Andersen, Jens B.,Givskov, Michael,Hultqvist, Louise D.,Jakobsen, Tim H.,Jansen, Charlotte U.,Nielsen, Thomas E.,Nilsson, Martin,Qvortrup, Katrine M.,Tolker-Nielsen, Tim,Uhd, Jesper
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supporting information
p. 1868 - 1878
(2021/12/22)
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- Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents
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Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.
- Silva, Daniel,Mendes, Eduarda,Summers, Eleanor J.,Neca, Ana,Jacinto, Ana C.,Reis, Telma,Agostinho, Paula,Bolea, Irene,Jimeno, M. Luisa,Mateus, M. Luisa,Oliveira-Campos, Ana M. F.,Unzeta, Mercedes,Marco-Contelles, José,Majekova, Magdalena,Ramsay, Rona R.,Carreiras, M. Carmo
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p. 215 - 231
(2019/09/03)
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- Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate as an HIV-1 replication inhibitor
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Inspired by the antiviral activity of known pyrazole-based HIV inhibitors, we screened our in-house library of pyrazole-based compounds to evaluate theirin celluloactivity against HIV-1 replication. Two hits with very similar structures appeared from single and multiple-round infection assays to be non-toxic and active in a dose-dependent manner. Chemical expansion of their series allowed an in-depth and consistent structure-activity-relationship study (SAR) to be built. Further ADME evaluation led to the selection of 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate with an advantageous pharmacokinetic profile. Finally, examination of its mode of action revealed that this compound does not belong to the three main classes of anti-HIV drugs, a feature of prime interest in the context of viral resistance.
- Alvarez, Karine,Busca, Patricia,Calvez, Vincent,Delelis, Olivier,Fichez, Jeanne,Gizzi, Patrick,Gravier-Pelletier, Christine,Le Corre, Laurent,Prestat, Guillaume,Sayon, Sophie,Soulie, Cathia,Marcelin, Anne-Geneviève,Priet, Stéphane
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p. 577 - 582
(2020/06/04)
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- Computer-aided molecular design of pyrazolotriazines targeting glycogen synthase kinase 3
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Numerous studies have highlighted the implications of the glycogen synthase kinase 3 (GSK-3) in several processes associated with Alzheimer’s disease (AD). Therefore, GSK-3 has become a crucial therapeutic target for the treatment of this neurodegenerative disorder. Hereby, we report the design and multistep synthesis of ethyl 4-oxo-pyrazolo[4,3-d][1–3]triazine-7-carboxylates and their biological evaluation as GSK-3 inhibitors. Molecular modelling studies allow us to develop this new scaffold optimising the chemical structure. Potential binding mode determination in the enzyme and the analysis of the key features in the catalytic site are also described. Furthermore, the ability of pyrazolotriazinones to cross the blood–brain barrier (BBB) was evaluated by passive diffusion and those who showed great GSK-3 inhibition and permeation to the central nervous system (CNS) showed neuroprotective properties against tau hyperphosphorylation in a cell-based model. These new brain permeable pyrazolotriazinones may be used for key in vivo studies and may be considered as new leads for further optimisation for the treatment of AD.
- Sciú, M. Lourdes,Sebastián-Pérez, Victor,Martinez-Gonzalez, Loreto,Benitez, Rocio,Perez, Daniel I.,Pérez, Concepción,Campillo, Nuria E.,Martinez, Ana,Moyano, E. Laura
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- Iodine-catalyzed diazenylation with arylhydrazine hydrochlorides in air
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A mild approach to diazenylation of active methylene compounds and N-heterocyclic compounds with arylhydrazine hydrochlorides in the presence of iodine under basic aerobic conditions was developed. The reaction could be executed either under heating or in the presence of blue LED light, though the latter condition was found to be relatively efficient. Presumably, the aryldiazene produced by oxidation of arylhydrazine hydrochloride acts as a nitrogen scavenger of the radical intermediate generated from the active methylene compound in the presence of iodine to produce the diazo compounds. The scope and limitations of the protocol are presented.
- Barak, Dinesh S.,Dighe, Shashikant U.,Avasthi, Ilesha,Batra, Sanjay
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p. 3537 - 3546
(2018/04/14)
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- FGFR3 ANTAGONISTS
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The invention pertains to novel FG-FR3antagonists of general formula (I), The compounds are useful for the treatments and prevention of achondroplasia and cancer.
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Paragraph 0089-0091
(2018/09/12)
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- Microwave-assisted preparation of 4-amino-3-cyano-5-methoxycarbonyl-N-arylpyrazoles as building blocks for the diversity-oriented synthesis of pyrazole-based polycyclic scaffolds
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The synthesis of 4-amino-3-cyano-N-arylpyrazoles A based on a Thorpe-Ziegler cyclization as the key step has been achieved using microwave activation. Via a new diversity-oriented synthetic pathway, these highly functionalized building blocks allowed the access to various heteroaromatic scaffolds such as pyrazolo-pyridines B, pyrazolo-pyrimidines C and pyrazolo-oxadiazoles D. Interestingly, these platforms contain three to four reactive sites that could be used for post-functionalization in order to further increase the molecular diversity.
- Corre, Laurent Le,Tak-Tak, Lotfi,Guillard, Arthur,Prestat, Guillaume,Gravier-Pelletier, Christine,Busca, Patricia
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p. 409 - 423
(2015/02/02)
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- Synthesis, absorption properties and biological evaluation of some novel disazo dyes derived from pyrazole derivatives
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In this study, 20 novel disazo dyes containing pyrazole derivatives were synthesized by a convenient method. Diazotized aniline and some aniline derivatives were reacted with malononitrile to give 2-arylazomalononitrile derivatives 1(a-e). The synthesized 2-arylazomalononitrile derivatives were reacted with hydrazine and phenyl hydrazine to afford the corresponding 3,5-diamino-4-arylazo-1 H-pyrazole 2(a-e) and 3,5-diamino-4-arylazo-1-phenylpyrazole 3(a-e). Diazotized compounds of 2(a-e)and 3(a-e) reacted with ethylacetoacetate to give 4-arylazo-3-amino-1 H-pyrazole-5-ylazo-ethylacetoacetate 4(a-e) and 4-arylazo-3-amino-1-phenylpyrazole-5-ylazo-ethylacetoacetate 7(ae). The obtained 4(a-e) and 7(a-e) were reacted with hydrazine and phenyl hydrazine to give disazo dyes 5(a-e), 6(a-e), 8(a-e) and 9(a-e), respectively. The synthesized disazo dyes were characterized by spectroscopic techniques as well as elemental analysis. The solvatochromic behaviours of these dyes in various solvents were examined. Acid-base effects on the absorption maxima of the dyes were also reported. Antimicrobial activities of the synthesized novel disazo dyes were investigated.
- Sener, Nesrin,Sener, Izzet,Yavuz, Serkan,Karci, Fikret
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p. 3003 - 3012
(2015/12/11)
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- Mechanically activated solid-state synthesis of phenylhydrazone derivatives via high-speed ball milling
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A series of phenylhydrazone derivatives was synthesized from arenediazonium tetrafluoroborates and active methylene compounds under high-speed ball milling. The reaction occurred in the absence of the solvent and products were obtained in good yield within short reaction times (no more than 30 min).
- Zhu, Xingyi,Chen, Yuanyuan,Chen, Yuhe,Wang, Jue,Su, Weike
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p. 621 - 626
(2014/07/21)
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- Multistep flow synthesis of 5-amino-2-aryl-2h-[1,2,3]-triazole-4-carbonitriles
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1,2,3-Triazole has become one of the most important heterocycles in contemporary medicinal chemistry. The development of the copper-catalyzed Huisgen cycloaddition has allowed the efficient synthesis of 1-substituted 1,2,3-triazoles. However, only a few methods are available for the selective preparation of 2-substituted 1,2,3-triazole isomers. In this context, we decided to develop an efficient flow synthesis for the preparation of various 2-aryl-1,2,3-triazoles. Our strategy involves a three-step synthesis under continuous-flow conditions that starts from the diazotization of anilines and subsequent reaction with malononitrile, followed by nucleophilic addition of amines, and finally employs a catalytic copper(II) cyclization. Potential safety hazards associated with the formation of reactive diazonium species have been addressed by inline quenching. The use of flow equipment allows reliable scale up processes with precise control of the reaction conditions. Synthesis of 2-substituted 1,2,3-triazoles has been achieved in good yields with excellent selectivities, thus providing a wide range of 1,2,3-triazoles.
- Jacq, Jér?me,Pasau, Patrick
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p. 12223 - 12233
(2015/03/31)
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- Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-ylacetonitriles
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In this study, some substituted phenylhydrazono-1H-tetrazol-5-yl- acetonitriles have been synthesized (2a-o, 2a and 2k are known compounds). The synthesized compounds were characterized by spectroscopic methods [Fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), mass spectroscopy (MS)]. In addition, antimicrobial activities of synthesized compounds were investigated against Bacillus cereus RSKK 863, Escherichia coli ATCC 3521, Pseudomonas aeruginosa ATCC 2921, and Staphylococcus aureus TP32. These compounds had antimicrobial effect against these bacteria (except for 21). Birkhaeuser Boston 2009.
- Yavuz, Serkan,Aydin, Oezlem,Cete, Servet,Disli, Ali,Yildirir, Yilmaz
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scheme or table
p. 120 - 126
(2010/12/20)
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- Microwave reaction of diazonium salts with nitrites
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A series of aryldiazonium tetrafluorborates dissolved in nitrites have been converted into the corresponding anilides in almost quantitative yield in 1 min by microwave irradiation. When bromoacetonitrile was used, 2,4-bis(bromophenyl) -quinazoline was formed. The reaction of malononitrile with the diazonium salt, in DMF as a solvent, afforded 2-(dimethylaminomethylene) malononitrile and phenylhydrazone propanedinitrile.
- Saez, Rebeca,Dolores Otero,Batanero, Belen,Barba, Fructuoso
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body text
p. 492 - 494
(2009/04/06)
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- Improved protocol for Thorpe reaction: Synthesis of 4-amino-1-arylpyrazole using solid-liquid phase-transfer conditions
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Solid-liquid phase-transfer conditions were employed for the first time in the Thorpe reaction to synthesize 4-amino-1-aryl-3,5-substituted-1H-pyrazoles 3. Aryl amines were diazotized and coupled with various active methylene compounds such as cyano aceta
- Desai, Nirmal D.,Shah, Rina D.
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p. 316 - 327
(2008/09/16)
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- 4-Arylazo-3,5-diamino-1H-pyrazole CDK inhibitors: SAR study, crystal structure in complex with CDK2, selectivity, and cellular effects
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In a routine screening of our small-molecule compound collection we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of ATP antagonists with moderate potency against CDK2-cyclin E. A preliminary SAR study based on 35 analogues suggests ways in which the pharmacophore could be further optimized, for example, via substitutions in the 4-aryl ring. Enzyme kinetics studies with the lead compound and X-ray crystallography of an inhibitor-CDK2 complex demonstrated that its mode of inhibition is competitive. Functional kinase assays confirmed the selectivity toward CDKs, with a preference for CDK9-cyclin T1. The most potent inhibitor, 4-[(3,5-diamino-1H-pyrazol-4-yl) diazenyl]phenol 31b (CAN508), reduced the frequency of S-phase cells of the cancer cell line HT-29 in antiproliferation assays. Further observed cellular effects included decreased phosphorylation of the retinoblastoma protein and the C-terminal domain of RNA polymerase II, inhibition of mRNA synthesis, and induction of the tumor suppressor protein p53, all of which are consistent with inhibition of CDK9.
- Kry?tof, Vladimír,Canka?, Petr,Fry?ová, Iveta,Slouka, Jan,Kontopidis, George,D?ubák, Petr,Hajdúch, Marián,Srovnal, Josef,De Azevedo Jr., Walter F.,Orság, Martin,Paprská?ová, Martina,Rol?ík, Jakub,Látr, Ale?,Fischer, Peter M.,Strnad, Miroslav
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p. 6500 - 6509
(2007/10/03)
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- A microwave assisted diazo coupling reaction: The synthesis of alkylazines and thienopyridazines
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Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c. Copyright Taylor & Francis Group, LLC.
- Al-Mousawi, Saleh,Elassar, Abdel-Zaher,El-Apasery, Morsy
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p. 1755 - 1771
(2007/10/03)
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- On the chemistry of cinnoline V [1]. Reactions of 4-aminocinnolines with amines
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We describe the effect of the solvent during the intra-cyclization of the arylhydrazonomalononitrile to obtain new and useful substituted cinnolines, namely 4-amino-3-cyanocinnolines and (4-amino-cinnolin-3-yl)arylmethanones. 4-Amino-3-cyano-5,7-dimethyl-cinnoline was treated with n-hexylamine, cyclohexylamine, and isopropylamine to yield the corresponding cinnoline-3-carboxamidine derivatives. Furthermore, 4-amino-3-cyano-5,7- dimethylcinnoline was reacted with diaminoethane to give 4-amino-5,7-dimethyl-3- (4,5-dihydroimidazol-2-yl)cinnoline. Treatment of 4-amino-3-cyano5,7- dimethylcinnoline with hydrazine hydrate provided 3-amino-7,9-dimethyl-1H- pyrazolo[4,3-c]cinnoline. Moreover, (4-aminocinnolin-3-yl)phenylmethanones were treated with hydrazine hydrate to give 3-phenyl-1H-pyrazolo[4,3-c]cinnolines. Finally, reactions of (4-aminocinnolin-3-yl)phenylmethanone with 3,5-dimethylaniline, phenyl hydrazine, hydroxylamine, and phenyl isothiocyanate are discussed. Chemical and spectroscopic evidence for the structures of the new compounds is presented. Springer-Verlag 2003.
- Amer, Atef M.,El-Mobayed, Mathat M.,Asker, Sherif
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p. 595 - 604
(2007/10/03)
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- Reactions with hydrazonoyl halides XIX1: Synthesis of some pyrazole and 5-arylazothiazole derivatives
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Hydrazonoyl chlorides 1 reacted with 2-aryl-1-cyano-1-thiazol-2-ylethenes 2 in presence of triethylamine to give the cycloadducts 4. which were converted to the corresponding pyrazoles 5 by the action of sodium methoxide. The reaction of hydrazonoyl halides 1 and 6 with each of 2-arylidene-2-cyanoethanethioamides 7 and 2-arylhydrazono-2-cyanoethanethioamides 14 in ethanolic triethylamine or ethanolic sodium hydroxide solutions, has been investigated. Structures of all the products were established on the basis of their spectral data and alternative synthesis.
- Zohdi, Hussein F.,Rateb, Nora M.,Abdelhamid, Abdou O.
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p. 103 - 117
(2007/10/03)
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- Synthesis and Chemical Transformations of 1,3-Diaryltetrazolium Salts. Preparation of Mercury(II) and Palladium(II) Complexes of 1,3-Diaryltetrazolylene and Reactions of 5-Substituted 1,3-Diphenyltetrazolium Salts with Nucleophiles
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1,3-Diaryltetrazolium salts 5 and 6 have been prepared by nitric acid oxidation of the corresponding 5-thiolates 4.The reaction of 5 with mercury(II) acetate gives (1,3-diaryltetrazolylene)mercury(II) complexes 7, which provide 5-halotetrazolium salts 8-10 by treatment with halogen. 1,3-Diphenyltetrazolylene (16), generated in situ by proton abstraction of 1,3-diphenyltetrazolium salts 5a or 6a, has been trapped with p-(dimethylamino)benzenediazonium tetrafluoroborate to form 18/18'.The palladium(II) complex 19 of 1,3-diphenyltetrazolylene has been prepared by oxidative addition of tetrakis(triphenylphosphane)palladium(0) to 5-chlorotetrazolium salt 8.The reactivity of various 5-substituted tetrazolium salts toward carbon nucleophiles depends on the nature of the substituents at C-5.With electronegative substituents, nucleophilic substitution proceeds at C-5, whereas electron-donating substituents direct the nucleophiles towards N-2 yielding ring-cleaved products.Key Words: Mesoionic compounds / Tetrazolium salts, 1,3-diaryl / Carbenes, mesoionic / Carbene-metal complexes / Nucleophilic substitution
- Araki, Shuki,Wanibe, Yasumi,Uno, Fujio,Morikawa, Akinao,Yamamoto, Kaori,et al.
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p. 1149 - 1156
(2007/10/02)
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- KINETICS ANALYSIS OF THE DECAY OF PHENYLHYDRAZONOPROPANEDINITRILE ADDITION PRODUCTS WITH THIOLS IN AQUEOUS SOLUTIONS
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The reactions of phenylhydrazonopropanedinitriles with thiols are reversible and with increasing pH-values of aqueous solutions the equilibrium is shifted them to the side of the reactants.A mechanism of decay of corresponding addition products was proposed and the kinetic description based on this mechanism is in a good agreement with the obtained experimental data.From the viewpoint of the decay, the pH-dependent dissociation of the proton of the imino group formed by addition of thiol to the nitrile carbon atom plays a decisive role.The obtained knowledge is useful with respect to the use of phenylhydrazonopropanedinitriles as affinants for selective and reversible sorption of low-molecular thiols and thiol-proteins in affinity chromatography as well as for the study of the mechanism of the effect of these substances in oxidative and photosynthetic phosphorylation and biological systems in general.
- Antalik, Marian,Sturdik, Ernest,Podhradsky, Dusan,Polekova, Ingrid,Drobnica, Ludovit
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p. 3387 - 3396
(2007/10/02)
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- REVERSIBILITY OF REACTIONS OF PHENYLHYDRAZONOPROPANEDINITRILES WITH THIOLS
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S-Benzyl (2-phenylhydrazono)cyanothioacetimidate, as a model product of the reaction of phenylhydrazonopropanedinitriles with thiols, is decomposed in physiological medium into the original reactants, i.e. benzyl mercaptan and phenylhydrazonopropanedinitr
- Sturdik, Ernest,Antalik, Marian,Drobnica, Ludovit
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p. 437 - 442
(2007/10/02)
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