• Title/Summary/Keyword: sulfonamide

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

  • Chae, Jong-Kun;Lee, Jae-Seob;Choi, Jung-Do;Shin, Jung-Hyu
    • Applied Biological Chemistry
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    • v.41 no.1
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    • pp.99-103
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    • 1998
  • Triazolopyrimidine sulfonanilide (TP) derivative is one of excellent herbicide compounds. We have synthesized three classes of a new sulfonamide derivative (TPP) as Acetolactate synthase (ALS) inhibitors, in which the benzene ring in TP skeleton was converted to substituted pyrimidyl ring and examined their inhibitory activities on barley for ALS. $I_{50}$ values of the inhibitors ranged from 0.005 to 2 mM. Comparing the $I_{50}$ value of each class of TPP derivatives, the substituents in pyrimidine and triazolopyrimidine ring were found to affect the degree of ALS inhibition. TPP with substituted methyl group in pyrimidine ring showed higher inhibitory activity than that with methoxy group, while the substitution of the cyclopentano group in triazolopyrimidine ring gave very large inhibitory activity than that of methyl group. The present study established that variation of the electron density by substitution at heterocyclic ring is a very important factor for ALS inhibition, but showed no dependence on steric effect by substituents.

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Organization of Antibiotic Resistance Gene Cluster of Multi-Drug Plasmid in Clinically Isolated Salmonella Enteritidis Strain (식중독환자에서 분리한 Salmonella Enteritidis 다제내성 플라스미드의 내성유전자 집락의 구조해석)

  • Jung, Seo-Yeon;Son, Chang-Kyu;Kwak Kyung-Tak;Kim, Byung-Chun;Park, Wan
    • Korean Journal of Microbiology
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    • v.38 no.4
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    • pp.299-305
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    • 2002
  • Clinically isolated Salmonella Enteritidis strain has a multi drug resistance plasmid, which confers ampicillin, chloramphe-nicol, sulfonamide, streptomycin and tetracycline, named pCAST2. We cloned a 7 kb Sacl fragment of pCAST2 which has sulfonamide, streptomycin and tetracycline resistance genes. The 7 kb SacI fragment showed the organization of sulII-strA-strB-tetR-tetA gene cluster which is different from the other clusters reported previously. In this study, we presented the method to detect this cluster by PCR analysis and showed that this cluster was found in Salmonella strains occurred sporadically at Kyungpook province in 2002.

Synthesis of Indoline tri-isopropyl benzene sulfonamide as a potential new asymmetric catalyst (새로운 술폰아미드계의 촉매의 합성)

  • Yun, In-Gwon;Kim, Hwan-Cheol
    • The Journal of Natural Sciences
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    • v.7
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    • pp.47-51
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    • 1995
  • In order to develope new asymmetric catalyst, we synthesized the following new sulfonamide derivatives start from S-Indoline-2-Carboxylic Acid via the following 5 steps. Hydroxy methyl derivative(1) was thus treated with methane sulfonyl chloride in the presence of triethylamine as base to give mesylated derivative(2) in 85% of isolated yield. The mesylate compound (2) was treated with excess sodium azide to give Azido derivative (4) in 95% isolated yield. Azido compound (3) was then reduced to the corresponding amino derivative in near quntitative yield by the hydrogenation under hydrogen atmospere in the presence of catalytic amount of Pd-C. The amino derivative (4) was converted to its sulfonamide derivatives by the treatment of compound(4) with triisopropyl benzene sulfonyl chloride in the presence of triethyl amine as base. Finally t-BOC group of the compound(5) was removed by the treatement of excess Trifluoro-acetic acid in near quantitative yield to give the target sulfonamide derivative (7) .in this paper we prepared compound(6) in 49% overall yield via the 5 steps of synthesis starting from t-Boc- 2-hydroxy methyl indoline(1) which cab be easily prepared from commercial available S-indoline-2-carboxylic acid by known methods. we plan to apply this new catalyst for the asymmetric reduction , diels-alder reaction, aldolcondensation reaction in due courses.

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Removal Characteristics of Sulfonamide Antibiotic Compounds in Biological Activated Carbon Process (생물활성탄 공정에서의 Sulfonamide계 항생물질 제거특성)

  • Son, Hee-Jong;Jung, Jong-Moon;Roh, Jae-Soon;Yu, Pyung-Jong
    • Journal of Korean Society of Environmental Engineers
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    • v.31 no.2
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    • pp.96-101
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    • 2009
  • In this study, the effects of three different biological activated carbon (BAC) materials (each coal, coconut and wood based activated carbons), empty bed contact time (EBCT) and water temperature on the removal of sulfonamide 5 species in BAC filters were investigated. Experiments were conducted at three water temperatures (5, 15 and $25^{\circ}C$) and four EBCTs (5, 10, 15 and 20 min). The results indicated that coal based BAC retained more attached bacterial biomass on the surface of the activated carbon than the other BACs, increasing EBCT or increasing water temperature increased the sulfonamide 5 species removal in BAC columns. In the coal-based BAC columns, sulfachloropyridazine (SCP), sulfamethazine (SMT) and sulfathiazole (STZ) removal efficiencies were 30~80% and sulfadimethoxine (SDM), sulfamethoxazole (SMX) removal efficiencies were 18~70% for 5~20 min EBCT at $25^{\circ}C$. The kinetic analysis suggested a first-order reaction model for sulfonamide 5 species removal at various water temperatures (5~$25^{\circ}C$). The pseudo-first-order reaction rate constants and half-lives were also calculated for sulfonamide 5 species removal at 5~$25^{\circ}C$. The reaction rate and half-lives of sulfonamide 5 species ranging from 0.0094~0.0718 $min^{-1}$ and 9.7 to 73.7 min various water temperaturs and EBCTs in this study could be used to assist water utilities in designing and operating BAC filters for sulfonamide antibiotic compounds removal.

Studies on the detection of sulfonamide residues in swine edible tissues (돈육내 sulfonamides의 잔류물질 검출에 관한 연구)

  • Shin, Youn-kyung;Kim, Tae-jong;Yoon, Hwa-joong
    • Korean Journal of Veterinary Research
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    • v.34 no.4
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    • pp.843-850
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    • 1994
  • The study was carried out to determine the residues of sulfonamides in swine edible tissues with high performance thin layer chromatography. For this purpose, the Rf values of sulfonamides in various solvent systems and the recovery rate of sulfameathazine from sampike saples were obtained. Thirty-four samples collected from meat market in Seoul were analyzed. The results obtained from the present study were followings: 1. The average recovery rate of sulfamathazine residues from spiked tissues 0.05, 0.1, 0.5 and 1mg/kg sample weight was 85%. 2. Two of 34 samples of pork for domestic consumption were reported to have been exceeded 0.05 ppm in sulfamethazine residues degree. 3. On the basis of the results, the degree of residues of sulfamethazine in swine meat for domestic consumption is seemed not to be dangerous for public health.

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Determination of Sulfonamide Residues in Raw Milk from southern Kyeonggi Area (경기남부지역 원유중의 설파제 잔류조사)

  • 김창수;이성권;고태오;고신일
    • Korean Journal of Veterinary Service
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    • v.19 no.1
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    • pp.39-45
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    • 1996
  • Sulfonamides are widely used to treat mastitis of cattle in field. The study was carried out to analyze sulfonamid residues In raw milk from south Kyeonggi area. The milk sample was deproteinated with acetone and defatted with hexane. The residual sulfonamides were extracted with ethylacetate, concentrated under vaccum, reconstituted with the acetate buffer-methanol mixture, reacted with fluorescamine, and then analyzed by HPLC-fluorescence detector(EX. 39nm, Em. 495nm) with methanol : acetate buffer system(3/2, v /v) as a mobile phase. The results analyzed by Thin layer chromatography and High performance liquid chromatography were summarized as follows. 1. A total of 24 cases out of 478 raw milk samples(5.0%) collected during April and May showed positive reaction to sulfonamide residues. Among 24 positive reactors, 9 cases were positive to sulfanilamides(32.1%), 8 cases were positive to sulfathiazoles(28.6%) and 5 cases were positive to sulfamonomthoxines (7.9%) , respectively. 2. During July and August, 31 cases out of 464 raw milk samples(6.7%) showed positive re action to sulfonamide residues. Among them S cases were positive to sulfanilamides, 5 cases sulfathiazoles and 5 cases sulfamonomethoxines(16.1%), respectively.

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The study of analytical method for sulfonamide antibiotics and their metabolites in environmental samples (환경 시료 중 설폰아미드계 항생제 및 대사체 분석방법 연구)

  • Kang, Young-Yeul;Hwang, Seung-Ryul;Shin, Sun-Kyoung;Koo, So-Hyun;Sim, Ki-Tae;Kim, Tae-Seung
    • Analytical Science and Technology
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    • v.23 no.5
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    • pp.437-445
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    • 2010
  • The aim of this study was to develop an analytical method for sulfonamide antibiotics (sulfadiazine, sulfamerazine, sulfamethazine, sulfamethoxazole, sulfathiazole) and their metabolites ($N^4$-acetylsulfadiazine, $N^4$-acetylsulfamerazine, $N^4$-acetylsulfamethazine, $N^4$-acetylsulfamethoxazole, sulfamethoxazole-$N^1$-glucuronide) in environmental samples. The solid phase extraction (SPE) with LC/ESI-MS/MS have been used for the analysis of target compounds, and the recoveries of SPE clean-up were at the range of 12-94% for C18 cartridge, 60-95% for HLB cartridge, 25-123% for MCX cartridge, and 70-90% for tandem HLB/MCX. By established method, detection limit, recovery, and relative standard deviation were 0.001~0.187 ng/mL, 66~115%, and 5~17%, respectively. This method was effective and sensitive to use for the simultaneous determination of sulfonamide antibiotics and their metabolites in environmental samples. Four sulfonamide antibiotics were detected at the range of 0.008~2.153 ng/mL. For metabolites, only $N^4$-acetylsulfamethoxazole was detected, but the concentration was under the MDL level.

Determination and Temperature Dependence of n-Octanol/Water Partition Coefficients for Seven Sulfonamides from (298.15 to 333.15) K

  • Congliang, Zhang;Yan, Wang;Fuan, Wang
    • Bulletin of the Korean Chemical Society
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    • v.28 no.7
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    • pp.1183-1186
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    • 2007
  • A shake-flask method was used to determine the n-octanol/water partition coefficients of sulfamethazine, sulfadimethoxine, sulfamethoxydiazine, sulfamonomethoxine, sulfamethoxazole, sulfaquinoxaline and sulfachloropyrazine from (298.15 to 333.15) K. The results showed that the n-octanol/water partition coefficient of each sulfonamide decreased with the increase of temperature. Based on the fluid phase equilibrium theory, the thermodynamic relationship of n-octanol/water partition coefficient depending on the temperature is proposed, and the changes of enthalpy, entropy, and the Gibbs free energy function for sulfonamides partitioning in n-octanol/ water are determined, respectively. Sulfonamides molecules partitioning in n-octanol/water is mainly an enthalpy driving process, during which the order degrees of system increased. The temperature effect coefficient of n-octanol/water partition coefficient is discussed. The results show that its magnitude is the same as that of values in the literature.