• 제목/요약/키워드: Heterocyclic compounds

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할로겐을 소유한 이원소 고리 화합물에 관한 연구(제 3보) 유기산 또는 Lewis산 존재하에서 이루어진 초산 Furfuryl의 염소화반응 (Halogen Containing Heterocyclic Compounds (Part III) Chlorination of Furfuryl Acetate in Presence of Acid and Lewis Acids)

  • 김유선;이수선;오명원
    • 대한화학회지
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    • 제14권3호
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    • pp.201-206
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    • 1970
  • Furfuryl acetate was chlorinated in presence of acetic acid using carbontetrachloride as the solvent. When the chlorination proceeded at the low concentration of acetic acid, the formation of the tetrachloride was more efficient than that of higher concentration. The chlorination done in presence of various Lewis acids such as aluminum chloride, hydrogen fluoride, and borontrifluoride could not give high yield of tetrachloride, but trichloride. In case of borontrifluoride and hydrogen fluoride, the decomposition of the reaction mixture was apparent. The results were discussed in terms of the stability of furfuryl nucleus towards an electron acceptor and the convenient procedure of preparing trichloro furfuryl acetate was described.

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含할로겐 異元素環化合物에 關한 硏究 (第1報) Furfurylacetate 의 Chlorination 반응 (Halogen Containing Heterocyclic Compounds (Part 1) Chlorination of Furfurylacetate)

  • 김유선;정진성
    • 대한화학회지
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    • 제9권2호
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    • pp.81-87
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    • 1965
  • 醋酸풀퍼릴을 合成하여 여러가지 反應條件下에서 鹽素化시킨 結果 低溫反應에서 安定한 trans 四鹽化物(平均收率 25∼30%)을 生成하였고, 三鹽化物의 生成은 거의 없었다. 高溫反應에서는 反應生成物의 分解가 甚하였다. 鹽素化反應條件, 生成物의 分離方式 및 安定度, 立體化學構造에 對하여 各各 論及하였다.

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Enantioselective Reduction of Racemic Three-Membered Heterocyclic Compounds. 3. Reaction of Epoxides with B-Isopinocampheyl-9-borabicycolo[3.3.1]nonane-Potassium Hydride and Potassium B-Isopinocampheyl-9 boratabicyclo[3.3.1]nonane Systems$^1$

  • Cha, Jin-Soon;Lee, Kwang-Woo;Yoon, Nung-Min
    • Bulletin of the Korean Chemical Society
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    • 제8권5호
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    • pp.421-423
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    • 1987
  • The chiral B-isopinocampheyl-9-borabicyclo[3.3.1]nonane-potassium hydride (IPC-9-BBN-KH) and potassium B-isopinocampheyl-9-boratabicyclo[3.3.1]nonane (K IPC-9-BBNH) systems were applied to the enantioselective reduction of representative racemic epoxides, namely 1,2-epoxybutane, 1,2-epoxyoctane, 3,3-dimethyl-1,2-epoxybutane and styrene oxide. In the case of IPC-9-BBN-KH system, the optical yields are in the range of 8.3-37.4$\%$ ee. However, the system of K IPC-9-BBNH provides significantly lower optical yields, showing 7-22.5$\%$ ee. These results strongly suggest that the enantioselective coordination of chiral organoborane to the epoxy oxygen of racemic epoxides plays an important role in this resolution.

Activated Nitrites in Heterocyclic Synthesis: Syntheses of Thiazole, Pyrazole and 4H-l,4-Benzothiazine Derivatives

  • El-Taweel, Fathy Mohamed Abdel-Aziz;Hadi-Mashaly, Mohamed-Abdel;Ali-Elagamey, Abdel-Ghani
    • Archives of Pharmacal Research
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    • 제13권3호
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    • pp.261-264
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    • 1990
  • 4-Arylazo-3-phenyl-5-aminopyrazoles (5a, b) and substituted hydroxythiazoles 8a, b were synthesized from the reaction of 4a, b with hydrazine hydrate and mercaptoacetic acid respectively. Compounds 5a, b and 8a, b were also obtained from coupling of 2a, b with 6 and 7, respectively. 4H-1, 4-Benzothiazine 11 was prepared from 1 and 10. The resaction of the diazonium salts 2a-c with diethyl 3-amino-2-cyanopenet-2-en-1, 5-dicarboxylate 12 was also reported.

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Determination of Heterocyclic Amines and Acrylamide in Agricultural Products with Liquid Chromatography-Tandem Mass Spectrometry

  • Lee, Kyung-Jun;Lee, Gae-Ho;Kim, HaeSol;Oh, Min-Seok;Chu, Seok;Hwang, In Ju;Lee, Jee-yeon;Choi, Ari;Kim, Cho-il;Park, Hyun-Mee
    • Toxicological Research
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    • 제31권3호
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    • pp.255-264
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    • 2015
  • Heterocyclic amines (HCAs) and acrylamide are unintended hazardous substances generated by heating or processing of foods and are known as carcinogenic and mutagenic agents by the animal experiments. A simple method was established for a rapid and accurate determination of 12 types of HCAs (IQ, MeIQ, Glu-P-1, Glu-P-2, MeIQx, Trp-P-1, Trp-P-2, PhIP, $A{\alpha}C$, $MeA{\alpha}C$, Harman and Norharman) and acrylamide in three food matrices (non-fat liquid, non-fat solid and fat solid) by isotope dilution liquid chromatography-tandem mass spectrometry (LC-MS/MS). In every sample, a mixture of internal standards including $IQ-d_3$, $MeIQx-d_3$, $PhIP-d_3$, $Trp-P-2-^{13}C_2-^{15}N$ and $MeA{\alpha}C-d_3$ was spiked for quantification of HCAs and $^{13}C_3$-acrylamide was also spiked for the analysis of acrylamide. HCAs and acrylamide in sample were extracted with acetonitrile and water, respectively, and then two solid-phase extraction cartridges, ChemElut: HLB for HCAs and Accucat: HLB for acrylamide, were used for efficiently removing interferences such as pigment, lipid, polar, nonpolar and ionic compounds. Established method was validated in terms of recovery, accuracy, precision, limit of detection, limit of quantitation, and linearity. This method showed good precision (RSD < 20%), accuracy (71.8~119.1%) and recovery (66.0~118.9%). The detection limits were < 3.1 ng/g for all analytes. The correlation coefficients for all the HCAs and acrylamide were > 0.995, showing excellent linearity. These methods for the detection of HCAs and acrylamide by LC-MS/MS were applied to real samples and were successfully used for quantitative monitoring in the total diet study and this can be applied to risk assessment in various food matrices.

삼백초 Hexane 분획물의 Heterocyclic Amine 돌연변이성 조정효과 (Modulation of the Bacterial Mutagenicity for food-borne Mutagens by Hexane Fraction from Saururus chinesis (Lour.) Bail)

  • 이상호;박철우;박경아;이영춘;김무남;하영래
    • 한국환경성돌연변이발암원학회지
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    • 제18권1호
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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.

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새로운 Sulfonamide 유도체의 합성과 Acetolactate Synthase (ALS) 저해 (Synthesis of Sulfonamide Derivatives as New Herbicidal Compounds and Studies on Biological Activity)

  • 채종근;이재섭;최정도;신정휴
    • Applied Biological Chemistry
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    • 제41권1호
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    • pp.99-103
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    • 1998
  • Triazolopyrimidine sulfonanilide (TP) 유도체는 널리 사용되고 있는 제초제 중의 하나이다. 우리는 TP 유도체 화합물의 골격을 이루고 있는 벤젠 고리를 pyrimidine 고리로 치환시킨 새로운 3 종류의 sulfonamide 유도체(TPP)를 합성하고, 보리에서 추출한 acetolactate synthase (ALS)의 저해 활성도를 측정한 결과 0.005 부터 2 mM 사이의$I_{50}$값을 얻었다. $I_{50}$ 값의 비교에서 pyrimidine 고리에 methyl기가 치환된 TPP 유도체는 methoxy기가 치환된 유도체 보다 높은 저해 활성도를 나타내었다. 또한 triazolopyrimidine 고리에 cyclopentano 고리로 치환된 TPP 유도체는 methyl- 및 phenyl가 치환된 유도체보다 우수한 저해 활성도를 보였다. 따라서 새로운 TPP 유도체의 제초 효력은 치환기에 의한 분자내 전자 분포 변화와 밀접한 관계가 있으나 치환기의 크기에 따른 입체적 장애 요인은 저해 활성도에 전혀 영향이 없음을 알 수 있었다.

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마이크로파 가열 목재의 방염·방충 복합 보존처리 특성 (Characteristics of Flame Retardent and Mothproof Conservation of Microwave Heated wood)

  • 김종근;박철우;윤태호;임남기
    • Journal of the Korean Wood Science and Technology
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    • 제41권3호
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    • pp.234-246
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    • 2013
  • 목조주택의 골조 및 실내 외 마감용으로 사용되는 침엽수 구조재를 대상으로 방염 방충 보존처리제가 혼합된 약제에 마이크로파 가열 후 열기를 지닌체 침지하여 복합적인 기능화를 부여한 후 목재의 건조 스케줄, 방염 시험에 의한 화재 저항성과 흰개미에 의한 내충해성, 혼합 약제의 침투성 분석을 실시한 결과 마이크로파로 3 kW로 5분 급속 가열된 시험편은 목표 온도 및 함수율을 만족하는 것으로 나타났으며, 인산염과 헤테로고리화합물계가 혼합된 약제에 120분 침지할 경우 가장 높은 중량 증가율을 가지는 것으로 나타났다. 또한 방염 후 처리 물품 시험을 실시한 결과 인산염과 혼합된 약제는 방염기준을 모두 만족하는 것으로 나타났으며, 흰개미 투입 후 7일 사충율을 확인한 결과 인산염과 헤테로고리화합물계 혼합 약제 침투 시험편의 경우 96% 이상 높은 사충율을 나타냄으로서 가장 우수한 특성을 가지는 것으로 나타났다. 목재 내부로 약제 침투성 분석을 실시한 결과 목재 세포내부 전면에 있어 혼합약제가 침투된 것으로 나타나 목재의 방염성 및 방충 저항성 등에서 우수한 성능의 발현은 혼합 약제의 균일한 침투때문으로 판단된다.

Ethyl 1-Aminotetrazole-5-carboxylate로부터 유도된 헤테로고리 화합물들의 항균 활성 시험 (Antimicrobial Assessment of Some Heterocyclic Compounds Utilizing Ethyl 1-Aminotetrazole-5-carboxylate)

  • Taha, Mamdouh A. M.;El-Badry, Susan M.
    • 대한화학회지
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    • 제54권4호
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    • pp.414-418
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    • 2010
  • Ethyl 1-aminotetrazole-5-carboxylate (1)를 hydrazine hydrate와 반응시켜서 대응하는aminohydrazide 2를 합성한 후에, 화합물 2를carbon disulfide와 반응시켜서 1,3,4-oxadiazole-5-thiol structure 3을 합성하였다. 얻어진 화합물 3을 either chloroacetone 또는 ethyl chloroacetate와 반응시켜서S-acyl 1,3,4-oxadiazole 유도체인 4 와 5를 합성하였으며, 또한 hydrazine hydrate와 반응시켜서 4-amino-1,2,4-triazole-5-thiol 유도체인 6을 합성하였으며, 화합물 6을 glacial acetic acid와 반응시켜서 6-methyl-1,3,4-triazolo[3,4-b]-1,3,4-thiadiazole (7)을 합성하였다. 한편, 알려진 방법에 따라서, 화합물 1로부터 tetrazolo[5,1-f]-1,2,4-triazine 9을 얻은 다음에, 화합물 9를 carbon disulfide와 반응시켜서 8-thione 유도체인 10을 합성한 후에, 대응하는 화합물 11, 12 및 13을 합성하였다. 얻어진 화합물13을 이용하여1,2,4-triazolo[4,3-d]tetrazolo[5,1-f]-1,2,4-triazines 14와 15를 합성하였다. 새롭게 합성한 화합물들의 화학구조를 확인하였으며, 합성한 화합물들에 대한 항균 활성시험을 수행하였다.