• Journal of the Korean Chemical Society
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• v.23 no.2
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• pp.94-98
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• 1979

From the catalytic reductions of the respective 2-amino-, and 2-nitro-3,4-dihydro-5,6-dimethoxy-1(2H)-naphthalenone, a major reduction product of 2-amino-5,6-dimethoxy-1,2,3,4-tetrahydro-naphthalene was obtained, along with a minute amount of rearranged product, 5,6-dimethoxy-1,2,3,4-tetrahydro-2(1H)-naphthalenone. The unusual formation of 5,6-dimethoxy-1,2,3,4-tetrahydro-2(1H)-naphthalenone was verified on the basis of ir, and nmr spectra, and elemental analysis. A plausible mechanism for the rearrangement is proposed.

• Bulletin of the Korean Chemical Society
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• v.25 no.10
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• pp.1581-1584
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• 2004

• Journal of the Korean Chemical Society
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• v.39 no.7
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• pp.564-571
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• 1995

5-Amino-2H-1,2,4-thiadiazoline-3-one has been prepared from 2-thiobiuret through a oxidative cyclization under basic hydrogen peroxide condition. Lactam-lactim tautomerism of 5-amino-2H-1,2,4-thiadiazoline-3-one has been examined by spectroscopic methods and ab initio molecular orbital calculation. These results were shown that 5-amino-2H-1,2,4-thiadiazoline-3-one exists as lactam form. Reaction conditions for alkylating 5-amino-2H-1,2,4-thiadiazoline-3-one with alkyl halides in the presence of various bases were studied in DMF and $H_2O$-THF two phase system. $Li_2CO_3$ base in DMF method gave best result in this investigation. The alkylation has been taken place at N-2 position. The identification of the product is confirmed by spectral data of IR, $^1H$ NMR and $^13C$ NMR and the comparison of authentic sample, 5-amino-2-methyl-1,2,4-thiadiazolidine-3-one, obtained from the oxidative cyclization of 5-methyl-2-thiobiuret.

• Journal of the Korean Chemical Society
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• v.21 no.3
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• pp.187-192
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• 1977

An alternate synthesis of 2-amino-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene hydrochloride from 2-nitro-3,4-dihydro-5,6-dimethoxy-1(2H)-naphthalenone,was described and compared the overall yields and experimental procedures with the previous synthetic routes obtained from Neber rearrangement product, 2-amino-3,4-dihydro-5,6-dimethoxy-1(2H)-naphthalenone hydrochloride.

• YAKHAK HOEJI
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• v.52 no.6
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• pp.488-493
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• 2008

2-Aminothiazole ring as a bioisoster of catechol in dopamine has provided with good oral availability and lipophilic property. 2-Aminoindan, is a rigid form of dopamine, was evaluated as a dopamine D3 agonist with low neurotoxicity. Dopamine D3 agonist was evaluated as selective for the treatment of Parkinson's disease. In order to develop a novel dopamine D3 agonist, we tried to synthesize the aminothiazoloindenoxazine derivative that is a hybrid structure of aminoindenoxazine and thiazole ring. cis-2-Amino-1-indanol (2) was synthesized from 1,2-indandione-2-oxime by catalytic hydrogenation and it was treated with chloroacetyl chloride and NaH in benzene solution to give (${\pm}$)-cis-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one (6). Nitration of 6 by the mixed acid gave 8-nitro compound (7) and the carbonyl group of 7 was reduced with $LiAlH_4$ to afford compound (8). 8 was reduced to form (${\pm}$)-cis-8-amino-2,3,4,4a,5,9b-hexahydroindeno[1,2-b][1,4]oxazine (9) and finally it was cyclized with KSCN in glacial acetic acid to yield (${\pm}$)-cis-8-amino-2,3,4,4a,5,10b-hexahydrothiazolo[4,5-f]indeno[1,2-b][1,4]oxazine (10).

• Microbiology and Biotechnology Letters
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• v.15 no.6
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• pp.375-380
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• 1987

D-$\alpha$-Amino-$\varepsilon$-carpolactam racemase (EC 5.1.1) and L-$\alpha$-amino-$\varepsilon$-caprolactam hydrolase (EC 3.5.2) were fractionated from cell-free extracts of Alcaligenes eutrophus A52 using ammonium sulfate precipitation and DEAE-cellulose ion exchange chromatography. It was made sure that D-$\alpha$-amino-$\varepsilon$-caprolactam was converted to L-$\alpha$-amino-$\varepsilon$-caprolactam by racemase, and then hydrolyzed into L-lysine by hydrolase in Alcaligenes eutrophus A52. For the conversion of D-$\alpha$-amino-$\varepsilon$-caprolactam into L-lysine by cell-free extracts of Alcaligenes eutrophus A52, the optimum temperature and pH were 6$0^{\circ}C$ and 8.5 respectively. The results showed that 0.5% D-$\alpha$-amino-$\varepsilon$-caprolactam was converted to L-lysine at 55$^{\circ}C$ for 10 hr with a conversion rate of 98% by cell-free extracts containing 3.1mg of protein.

• 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.

• YAKHAK HOEJI
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• v.50 no.6
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• pp.403-408
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• 2006

1-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3- (3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with hydroxylamine, and reduction with an overall yield of 74%. 2-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3-(3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with isoamylnitrite, reduction in NaOH and reaction with HCI to form 5,6-dimethoxy-2-indanone, which was reacted with hydroxylamine and reduced with an overall yield of 42%. 5,6-Dimethoxyindan-1,2-dione-2-oxime, which was catalytically hydrogenated to afford cis-, and trans-1-amino-5,6-dimethoxyindan-1-ol as 3 : 1 ratio. This mixture was treated with Li and reacted with chloroacetyl chloride. Cis isomer was acylated and cyclized to synthesize rir -( ${\pm}$ )-7,8-dimethoxy-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one, but trans isomer was just acylated to form amide.

• Food Science of Animal Resources
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• v.29 no.6
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• pp.719-725
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• 2009

Heterocyclic aromatic amines (HCAs) are potent mutagens and possible human carcinogens that are formed during the heating of protein-rich foods. The effects of preheating treatment of beef patties using a microwave prior to frying at $220^{\circ}C$ for 10 min on each side on the reduction of HCAs (amino-carbolines and amino-imidazo-azaarenes) were evaluated. The amount of HCAs was then evaluated by solid-phase extraction and high pressure liquid chromatography (HPLC) analysis. The beef patties were treated by microwaving for various times (0, 1, 1.5, 2, or 3 min) before pan-frying. The results revealed the presence of 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2), 3-amino-1,4-dimethyl-5H-pyrido-[4,3-b] indole (Trp-P-1), 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole (Glu-P-1), 2-aminodipyrido[1,2-a:3',2'-d]imidazole (Glu-P-2), 9H-pyrido[3,4-b]indole (Norharman), 1-methyl-9H-pyrido[3,4-b]indole (Harman), 2-amino-9H-pyrido[2,3-b] indole ($A{\alpha}C$), 2-amino-3,8 dimethylimidazo[4,5-f]-quinoxaline (MeIQx) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine (PhIP) in all samples. However, microwave pretreatment for 1 min inhibited the formation of these HCAs by up to 90% when compared to the control.

• Environmental Mutagens and Carcinogens
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• v.18 no.1
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• pp.26-31
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• 1998

Antimutagenic activity of Saururus chinesis (Lour.) Bail was investigated for food-borne mutagens using S. typhimurium TA98. Methanol extract from Saururus Chinesis (Lour.) Bail was fractionated into hexane, chloroform, ethylacetate and butanol fractions, followed by determination of antimutagenic activity for food-borne mutagenic heterogenic amines (HCA). The hexane fraction exhibited a strong antimutagenic activity for 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,8-dimethylimidazo[4,5-f] quinoxaline (MeIQ), 2-amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline (MeIQx), 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), 3-amino-1-methyl-5H-pyroid[4,3-b]indole acetate (Trp-2-A); however its fraction rather enhanced the bacterial mutagenicity of 2-amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinozaline (4,8-diMeIQx) and 2-amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxline (7,8-diMeIQx). Active principle in the fraction was found to be two major compounds (${\gamma}$-crene B and epi-bicyclosesquiphellandrane) and 6 minor compounds (${\delta}$-caryophyllene, ${\gamma}$-elemene, ${\beta}$-cabebene, ${\delta}$-cadinene, ${\delta}$-selinene, and patchoulene). Modulation effect for the mutagenic activity of the food-borne mutagenic HCA by the fraction might be derived from a cumulative effect of each individual compounds. Hence, this hexane fraction might be use to reduce the production of mutagenic HCA during cooking process of protein-rich foods.