• Title/Summary/Keyword: Aromatic amines

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Ruthenium Catalyzed Synthesis of 1-Substituted Perhydroazocines from Primary Amines and 1,7-Heptanediol

  • Shim, Sang-Chul;Doh, Chil-Hoon;Yoon, Jeum-Ho;Lee, Dong-Yub;Youn, Young-Zoo
    • Bulletin of the Korean Chemical Society
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    • v.12 no.6
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    • pp.649-652
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    • 1991
  • The reaction of primary aromatic amines with 1,7-heptanediol in the presence of a catalytic amount of ruthenium complex in dioxane at $180^{\circ}C$ for 24 hours gave the corresponding 1-substituted perhydroazocines in moderate yield.

Studies on the Synthesis of Bis-dithiocarbamates as Prodrugs of Isothiocyanates (Isothiocyanate 유도체의 Prodrug를 위한 합성 연구)

  • 심영섭;정오영;김완주;이문희
    • YAKHAK HOEJI
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    • v.26 no.2
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    • pp.91-96
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    • 1982
  • In an attempt to design prodrugs for the Derivatives of the Isothiocyanates R-N=C=S were synthesized eleven novel bis-dithiocarbamates. The best way of preparing the dithiocarbamates was the formation of the dithiocarbonates followed by the reaction of the dithiocarbonates with amines. Thus, the treatment of the diols with carbon disulfide in the presense of potassium hydroxide afforded the potassium salts of the ditniocarbonic acids. The potassium salts were then reacted with alkyl halides to give the dithiocarbonates, which upon treatment with amines produces the dithiocarbamates. In case of vicinal diol (n=o in the above formula), only one of the hydroxy groups was reacted to give the mono-dithiocarbonate. The dithiocarbonates failed to react with amides and aromatic amines. Dithiocarbonates of the different types were obtained when the active double bonds, such as $CH_{2}=CH-Z$ , (Z are electron withdrawing groups), were allowed to react with the free dithiocarbonic acids produced in situ by carefully neutralizing the Potassium salts of the corresponding acids. These compounds are considered to be of some value as prodrugs for the active double bonds.

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A Study on Distribution Property of Micropollutants in Gwang-Yang Bay Sediment (광양만 저질에서의 미량오염물질 분포특성에 관한 연구)

  • Han Sang-Kuk;Park Ji-Young
    • Journal of Environmental Science International
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    • v.15 no.7
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    • pp.643-651
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    • 2006
  • This study investigated the distributive property of micropollutants in sediment around Gwang-yang bay using simultaneous analytical method of 310 chemicals. In the results, the major micropollutants detected were CH type chemicals such as aliphatic, polycyclic compounds, benzenes, and CHN(O) type chemicals aromatic amines, and pesticides. Insecticides of pesticide type were frequently detected at all sampling site. The total concentration of micropollutants were higher in summer than in winter and measured within the range of $ND{\sim}36.50{\mu}g/L$. Also, because of effect of seomjin river, GY6 of all sampling site detected by the highest concentration, GY10 and 11 located in Gwang-yang outside bay were not detected the micropollutants. From the result of this study, we should estimated that the industrial complex located in Gwang-yang inside bay and an inflow of fresh water through the Seomjin river are major pollution sources of Gwang-yang bay.

Influence of Food Ingredients on the Formation of Heterocyclic Aromatic Amine in Cooked Pork Patties

  • Shin, Han-Seung
    • 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.

Evaluation of the in vitro biological activity of selected 35 chemicals (35종의 특정 화학성분들의 in vitro 활성 평가)

  • Shin, Han-Jae;Sohn, Hyung-Ok;Park, Chul-Hoon;Lee, Hyeong-Seok;Min, Young-Keun;Hyun, Hak-Chul
    • Journal of the Korean Society of Tobacco Science
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    • v.29 no.1
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    • pp.30-40
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    • 2007
  • The objective of this study was to investigate the contribution of various smoke constituents to the toxicological activity of total particulate matter(TPM) or the gas/vapor phase(GVP). These components included phenol compounds, aromatic amines, polycyclic aromatic hydrocarbons, heterocyclic amines, and carbonyl compounds. The mutagenic and cytotoxic potencies were assessed using the Salmonella mutagenicity assay with S. typimurium TA98 strain and the neutral red uptake cytotoxicity assay(NRU) with BALB/c 3T3 fibroblast cells, respectively. The Salmonella mutagenicity test showed that heterocyclic amines exhibited significantly higher levels of toxicity compared to other smoke constituents. Among them, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline(MeIQ) was shown the most mutagenic compound with a specific mutagenicity of $7.9{\times}10^5\;revertants/{\mu}g$. An analysis of the possible contribution revealed that MeIQ account for only 0.85% of the 2R4F-TPM mutagenicity in TA98. NRU data demonstrated that high cytotoxic activity was obtained for hydroquinone, formaldehyde, and acrolein. Based on the results of the present study, the contribution of acrolein to the cytotoxicity of the GVP fraction was calculated as 61%. Thus, a large proportion of the cytotoxic activity of this complex mixture, cigarette smoke gas phase, can be attributed to the acrolein.

Enantiodiscrimination and molecular docking study of chiral amines as 2-hydroxynaphthaldimine derivatives using amylose derived chiral selectors

  • Suraj Adhikari;Inhee Kang;Swapnil Bhujbal;Wonjae Lee
    • Analytical Science and Technology
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    • v.37 no.5
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    • pp.306-314
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    • 2024
  • This study describes the liquid chromatographic enantiomer separation of three typical chiral amines (α-methylbenzylamine, 2-amino-4-methyl-1-pentanol, and 1-methylheptylamine) as 2-hydroxynaphthaldimine derivatives using six amylose trisphenylcarbamates derived chiral stationary phases (CSPs). It was observed that the structural nature of three chiral amines and the structures of amylose chiral selectors can affect their chiral recognition ability. Among the three analytes as 2-hydroxynaphthaldimine derivatives, in general, the greatest enantioselectivities of aromatic amine analyte (α-methylbenzylamine) were achieved on amylose trisphenylcarbamate derived CSPs and were followed by amino alcohol analyte (2-amino-4-methyl-1-pentanol), and aliphatic amine analyte (1-methylheptylamine). Also, the enantiodiscrimination abilities obtained on the two CSPs, Chiralpak ID and Chiralpak IF, were selectively higher than the other four amylose trisphenylcarbamate derived CSPs for the studied analytes. The underlying chiral recognition mechanism between 2-amino-4-methyl-1-pentanol as 2-hydroxynaphthaldimine derivatives and amylose tris(3,5-dimethylphenylcarbamate) chiral selector of Chiralpak AD-H and Lux Amylose-1 was elucidated by molecular docking study, and it was observed that the intermolecular hydrogen bonding interactions by hydroxyl moiety on the amino alcohol analyte as 2-hydroxynaphthaldimine derivatives were the main interactive forces driving the chiral separation. The obtained binding energies between 2-amino-4-methyl-1-pentanol analyte as 2-hydroxynaphthaldimine derivative and amylose tris(3,5-dimethylphenylcarbamate) chiral selector were in agreement with the experimentally determined enantioseparation and elution order by chiral HPLC.

Synthesis and Biological Evaluation of Some Novel [4-(1H-Benzoimidazol-2-yl)-thiazol-2-yl]-benzylidene-amines and N-[4-(1H-Benzoimidazol-2-yl)-thiazol-2-yl]-N'-benzylidene-hydrazines

  • Mekala, Raghu Vardhan Reddy;Danda, Ravinder Reddy;Gadegoni, Hemalatha
    • Journal of the Korean Chemical Society
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    • v.57 no.1
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    • pp.94-98
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    • 2013
  • A new family of thiazole heterocycles, namely [4-(1H-benzoimidazol-2-yl)-thiazol-2-yl]-benzylidene-amines has been synthesized by the condensation of 4-(1H-Benzoimidazol-2-yl)-thiazol-2-ylamine with various aromatic aldehydes and N-[4-(1H-benzoimidazol-2-yl)-thiazol-2-yl]-N'-benzylidene-hydrazines through the cyclization of 1-(1H-benzoimidazol-2-yl)-2-bromo-ethanone with arylthiosemicarbazones. The target compounds are achieved by using 1-(1H-Benzoimidazol-2-yl)-ethanone as starting material. The chemical structures of all newly synthesized compounds were confirmed by their IR, $^1H$ NMR and Mass spectral data. Further the compounds were used to evaluate their antimicrobial activity and found that the appreciable antimicrobial activity by some of the title compounds.

Selective Synthesis of N-(Cyclohexylmethyl)-N-alkylamines from Primary Amines and Pimelaldehyde using Tetracarbonylhydridoferrate, $HFe(CO)_4^\;-$, as a Reducing Agent

  • Sang Chul Shim;Young Gil Kwon;Chil Hoon Doh;Byung Won Woo;Jin Ook Baeg;Hong Seok Kim;Tae Jeong Kim;Dong Ho Lee;Young Woo Kwak;Jin Soon Cha;Hyung Soo Lee;Jae Kook Uhm;Young Bae Park
    • Bulletin of the Korean Chemical Society
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    • v.11 no.2
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    • pp.140-143
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    • 1990
  • Ethanolic tetra carbonylhydridoferrate solution combined with dialdehyde (no of carbon; 4,5,6) is very efficient for the selective transformation of amino group into N-heterocyclic compound. However, a large variety of both aliphatic and aromatic amines react with the ferrate-pimelaldehyde at room temperature under an atmospheric pressure of carbon monoxide to give the corresponding N-(cyclohexylmethyl)-N-alkyiamine derivatives in moderate yields instead of the corresponding N-substituted perhydroazocine derivatives.