• Bulletin of the Korean Chemical Society
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• v.34 no.12
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• pp.3553-3558
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• 2013

The three dimensional-quantitative structure activity relationship (3D-QSAR) studies on chemical features of pyridine-2-amines in the external region of c-Met active site (ER chemical features of pyridine-2-amines) were conducted by docking, comparative molecular field analysis (CoMFA), and topomer CoMFA methods. The CoMFA model obtained the partial least-squares (PLS) statistical results, cross-validated correlation coefficient ($q^2$) of 0.703, non cross-validated correlation coefficient ($r^2$) of 0.947 with standard error of estimate (SEE) of 0.23 and the topomer CoMFA obtained $q^2$ of 0.803, $r^2$ of 0.940, and SEE of 0.24. Further, the test set was applied to validate predictive abilities of models, where the predictive $r^2$ ($r{^2}_{pred}$) for CoMFA and topomer CoMFA models were 0.746 and 0.608, respectively. Each contribution of ER chemical features of pyridine-2-amines to the inhibitory potency showed correlation coefficients, $r^2$ of 0.670 and 0.913 for two core parts, 3-(benzo[d]oxazol-2-yl)pyridine-2-amine and 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy) pyridine-2-amine, respectively, with corresponding experimental $pIC_{50}$.

• Journal of the Korean Chemical Society
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• v.11 no.4
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• pp.126-131
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• 1967

Various amines (Triethylamine, Diethylamine, Dimethylaniline, Pyridine and Diphenylamine) and electron acceptors (Carbontetrachloride, iodine monochloride and iodine) were reacted in the hexane solvent system to form a charge transfer complex in each case. The tendency of forming a charge transfer complex by these electron acceptors was proportional to the basicity of amines and the different type of complex was formed as the polarity of electron donor had markedly changed, which were identified by ultraviolet spectrophotometry. A correlation between the formation of complex and the basicity of amine and the polarity of electron acceptor was discussed.

• Journal of the Korean Chemical Society
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• v.6 no.2
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• pp.148-154
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• 1962

The reactions between organic halides$(CCl_4,\;C_6H_5Br,\;C_6H_5Cl,\;C_6H_5I)$ and amines $(C_6H_5NH_2,\;R_2NH,\;R_3N,\;(CH_2)_5NH,\;pyridine)$ were studied under mixed u.v. irradiation. The modes of reactions were examined by means of gas chromatography and product-reactant ratio determination. The reaction of $CCl_4$ with amines give chloroform and hexachloroethanes, and the reaction of aromatic halides with amines gave biphenyl and benzene. In each series of reaction there obtained mainly corresponding amine hydrohalides, but no amination products. The reactivity was in the order of the basicity of amines and of the reactivity of organic hahides, except in the case of cyclic tertiary amine. The result was interpreted as a non-chain photodecomposition process. A competitive proton abstraction reaction path via the formation of a change transfer complex was proposed as the reaction mechanism.

• Journal of the Korean Chemical Society
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• v.57 no.3
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• pp.361-364
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• 2013

A modified synthetic approach to the synthesis of heterocyclic food mutagens, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PHIP) and 2-amino-1,6-dimethylimidazo[4,5-b]pyridine (DMIP) is reported. This route highlights an optimized palladium catalysed Buchwald cross-coupling of 2-halo-1-methyl-imidazo[4,5-b]pyridine with benzophenoneimine followed by acidic hydrolysis to yield compound 7. Using finely tailored conditions, Suzuki cross-coupling reactions with highly efficient catalytic systems were performed as the final step on 8 to introduce the aryl group and methyl group on the heterocyclic core.

• Bulletin of the Korean Chemical Society
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• v.15 no.10
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• pp.873-881
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• 1994

The approximate rate and stoichiometry of the reaction of excess diisobutylaluminum hydride-dimethyl sulfide complex($DIBAH-SMe_2$) with organic compounds containing representative functional group under standardized conditions (toluene, $0{\circ}C$) were examined in order to define the reducing characterstics of the reagent and to compare the reducing power with DIBAH itself. In general, the reducing action of the complex is similar to that of DIBAH. However, the reducing power of the complex is weaker than that of DIBAH. All of the active hydrogen compounds including alcohols, amines, and thiols evolve hydrogen slowly. Aldehydes and ketones are reduced readily and quantitatively to give the corresponding alcohols. However, $DIBAH-SMe_2$ reduces carboxylic acids at a faster rate than DIBAH alone to the corresponding alcohols with a partial evolution of hydrogen. Similarly, acid chlorides, esters, and epoxides are readily reduced to the corresponding alcohols, but the reduction rate is much slower than that of DIBAH alone. Both primary aliphatic and aromatic amides examined evolve 1 equiv of hydrogen rapidly and are reduced slowly to the amines. Tertiary amides readily utilize 2 equiv of hydride for reduction. Nitriles consume 1 equiv of hydride rapidly but further hydride uptake is quite slow. Nitro compounds, azobenzene, and azoxybenzene are reduced moderately. Cyclohexanone oxime liberates ca. 0.8 equiv of hydrogen rapidly and is reduced to the N-hydroxylamine stage. Phenyl isocyanate is rapidly reduced to the imine stage, but further hydride uptake is quite sluggish. Pyridine reacts at a moderate rate with an uptake of one hydride in 48 h, while pyridine N-oxide reacts rapidly with consumption of 2 equiv of hydride for reduction in 6h. Similarly, disulfides and sulfoxide are readily reduced, whereas sulfide, sulfone, and sulfonic acid are inert to this reagent under these reaction conditions.

• Food Science of Animal Resources
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• v.31 no.4
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• pp.563-569
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• 2011

Heterocyclic amines (HCAs) are food mutagens and carcinogens that are found in cooked fish, meat, and protein-rich foods. This study examined the inhibitory effect of marinades containing a Nelumbo nucifera leaf fraction on HCA formation in cooked beef steak. As a result of the Ames assay, cooked beef marinated with the N. nucifera leaf butanol fraction (2.0 g) cooked at $190^{\circ}C$ showed a 61.5% reduction in overall mutagenicity. However, these data revealed no significant difference in mutagenicity in the ethanol, ethyl acetate, or water fractions. Formation of MeIQx (2-amino-3,8 dimethylimidazo[4,5-f]-quinoxalin) and PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine) was inhibited 60.7-63.5%. Cooked beef marinated with the water fraction of the N. nucifera leaf significantly (p<0.05) reduced the formation of MeIQx, PhIP, and DiMeIQx (2-amino-3,4,8 trimethylimidazo[4,5-f]-quinoxaline) by 65.3, 67.6, and 73.9%, respectively. These results show that marinades containing the N. nucifera leaf fraction could be an alternative method for reducing HCA formation in cooked beef steak.

• Journal of the Korean Chemical Society
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• v.54 no.6
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• pp.737-743
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• 2010

Coupling of 5-amino-1,3-diaryl-pyrazoles 1a-c with diazonium salts of different aryl amines gave a series of novel 1,3-diaryl-5-amino-4-arylazopyrazoles 3a-l. Such compounds could be also obtained by reaction of 5-amino-1,3-diaryl-4-nitroso- 1H-pyrazoles 2a-c with different aryl amines in alkaline medium. Oxidation of azo derivatives 3a-l with cupric acetate, in dimethyl formamide and stream of air, gave 2,4,6-triaryl-2,4-dihydropyrazolo [4,3-d]-1,2,3-triazoles 4a-l. and the fluorescence properties of the cyclic triazoles were studied. Diazotization of 5-amino-1,3-diaryl-1H-pyrazoles 1a-c by sodium nitrite in ortho-phosphoric acid followed by coupling with some aryl amines gave o-aminoazo compounds 5a-f. Cyclisation of compounds 5a-f in pyridine and cupric acetate gave the corresponding triazoles 6a-f. The coupling of compounds 6a-f with different aryl diazonium salts gave compounds 7a-j. The synthesized dyes were applied to polyesters as disperse dyes and the fastness properties were evaluated.

• Journal of the Korean Chemical Society
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• v.25 no.2
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• pp.110-118
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• 1981

Kinetics and mechanism for the reaction of substituted phenacyl bromides with substituted pyridines have been determined at 25, 35 and $45^{\circ}C$ in methanol and dimethylformamide by the conductivity method. The rate constants for the reaction of various pyridines with phenacyl bromide shown that electron-donating substituents in the pyridine increase the rate, while electron-attracting one decrease in both solvents. The effect of substituents in substrate, the rate being increased by electron-attracting substituents. This is as expected for nucleophilic attack of amines on the carbon atom. Isokinetic and $Br{\psi}nsted$ linear relationship were shown in the reaction of phenacyl bromide with pyridines in both solvent in which isokinetic temperature were obtained 614, $202^{\circ}K$ and ${\beta}$ values were 0.29, 0.36 in methanol and dimethylformamide respectively. In the case of the reaction of substituted phenacyl bromide with pyridines, isokinetic temperature decreases with increasing electron-attracting ability of the substituents in the phenacyl bromide, while the ${\beta}$ values were reverse. From the above results, it can be inferred that N…C bond formation decreases progressively from p-chloro- to p-methoxyphenacyl bromide and the bond formation predominates in DMF than methanol. The ${\rho}$ values of Hammett equation of the reaction of phenacyl bromide with substituted pyridines are negative in both solvent, but its value was larger negative in DMF than methanol and the ${\rho}$ value of that of substitutted substrates with pyridine was 0.3, the low value is ascribed to direct $S_N2$ attack of the nitrogen atom in pyridine ring at the methylene carbon.

• Food Science and Biotechnology
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• v.14 no.5
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• pp.572-575
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• 2005

The effects of cooking method, cooking time and various food ingredients on the formation/ inhibition of heterocyclic aromatic amines (HAAs) in pork products were investigated. Three HAAs, 2-amino-3,8-dimethylimidazo [4,5-f] quinoxaline ($MeIQ_x$), 2-amino-3,4,8-trimethylimidazo [4,5-f] quinoxaline ($DiMeIQ_x$) and 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) were measured in pork products using solid-phase extraction and HPLC. Pork patties were boiled, oven-broiled and pan-fried to internal temperatures of 71, 77 and $88^{\circ}C$. Generally, HAA concentrations increased with increasing internal temperature, and HAA formation was greatest with pan-fried. Selected food ingredients (vitamin E, sodium nitrite, sodium tripolyphosphate, sodium ascorbate, Nanking cherry tissue and cherry tissue extract) inhibited HAA formation in pork patties fried at $225^{\circ}C$ for 10 min/side, with the greater inhibition provided by cherry tissue and its methanolic extract.

• Journal of the Korean Applied Science and Technology
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• v.26 no.1
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• pp.29-37
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• 2009

This study is focused on the synthesis of urea and amide derivatives particularly, since the amide moiety is an essential binding group at the binding site. Urea derivatives 3-7 and 13-14 were obtained by reaction of 2-aminopyrimidines and other amines with diverse isocyanates in pyridine as a solvent under reflux. The urea derivatives were obtained in low yield because of the highly electron deficient nature of the amino group of the 2-aminopyrimidine. Amide derivatives 8-10 were obtained in moderate yields by reaction of compound 1 with aryl chloride derivatives. Also, arylamine 11 was synthesized by Buchwald-Hartwig amination in moderate yields. Most of the compound did not show good activity against A375P melanoma cells, compared with Sorafenib as control compound.