• 약학회지
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• 제41권4호
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• pp.473-479
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• 1997

New cephalosporin antibiotics, 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido]-3-substituted-3-cephem-4-carboxylic acid derivatives 2a-2d, 7 -[(3,4-dihydro-6-ethoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido] -3-substituted-3-cephem-4-carboxylic acid derivatives 3a-3d and 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl-1-(S)-oxide)acetamido]-3-substituted-3-cephem-4-carboxylic acid derivatives 4a-4d were synthesized. Antibacterial activities of these new cephalosporin derivatives and the relationship between their structures and their activities were examined. Among them, 7-[(3,4-dihydro-6-methoxycaronyl-2,2-dimethyl-2H-1,4-thiazin-3-yl-1-(S)oxide)-acetamido]-3-[(1,2,3-triazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid 4d exhibited the antibacterial activities against Gram(+)and Gram(-) bacteria.

• Bulletin of the Korean Chemical Society
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• 제9권3호
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• pp.164-166
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• 1988

7-Dithiocarboxy-3-phenyl-5,6-dihydro imidazo[2,1-b]thiazolium-betaine (2) was prepared by treatment of 3-phenyl-5,6-dihydro imidazo[2,1-b]thiazole (1) with carbon disulfide in acetone at room temperature. On the reaction of 2 with para-substituted phenacyl bromides (4) having the electron withdrawing property by virtue of (+) resonance (R) < (-) inductive (I) or (-) resonance (R), (-) inductive (I) effect, ring transformation product p-substituted-2-[2-[7-(p-substituted benzoyl)-5-thioxo-2,3-dihydro-1H-imidazo[1,2-c] thiazol-1-yl]-2-phenylvinylthio] acetophenone (6) was obtained; however, when R is electron donating grops with (+) resonance (R) > (-) inductive (I) effect the quarternary ammonium salt 7-(p-substituted phenyl) carbonyl methyl-3-phenyl-5,6-dihydro imidazo [2,1-b] thiazolium bromide (8) is formed. The reaction of 2 with unsubstituted-phenacyl bromide (R = H), on the other hand, gives 6a and 8a to the similar ratio, respectively.

• 대한화학회지
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• 제38권7호
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• pp.521-525
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• 1994

새로운 cephalosporin 항생물질인 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido]-3-heterocyclothiomethyl-3-cephem-4-carboxylic acid 유도체(2a∼2d)들을 합성하여, 구조변화에 대한 항균활성을 측정하였다. 그 중에서 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido]-3-[(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid가 그람양성 및 음성균에 대하여 광범위한 향균능력ㅇ르 나타내었다.

• 대한화학회지
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• 제46권4호
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• pp.330-336
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• 2002

새로운 ${\alpha},{\beta}$-불포화Carboxanilide계열의 살균제를 개발을 목적으로 4-acetyl-3-methyl-N-phenyl-1,4-thiazine-2-Carboxamide(6)의 합성에 대하여 기술하였다. Dihydro-1,4-thiazine methyl ester 11을 산화하여 생성된 sulfoxide 7을 Pummerer 반응하여 $\alpha$-acetoxy dihydro-1,4-thiazine 10a를 얻었다. 반며에 Dihydro-1,4-thiazine Carboxanilide sulfoxide14는 동일한 반응조건 하에서 중간체 sulfonium ion의 carboxanilide기가 관여한 vinylogous Pummerer 반응의 전위에 의하여 중간체를 15를 통하여 acetoxymethyl dihydro-1,4-thiazine 18이 생성되었다. 1,4-Thiazine carboxanilide 6은 $\alpha$-acetoxy dihydro-1,4-thiazine 10a를 산촉매로 처리한 다음 생성된 21a를 가수분해하고 아닐린과 결합하여 합성하였다

• 약학회지
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• 제37권2호
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• pp.136-142
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• 1993

To a suspension of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-{3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl}-4-oxo-3-quinoline carboxylic acid(C1) in sodium hydroxide solution and water is added dropwise with stirring carbon disulfide. [6R-[6$\alpha$, 7$\beta$(Z)]]-7-[[[2-Amino-4-thiazoly)methoxyimino]-acetyl]amino]-3-[[[[7-( 3-carboxy-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-guinolonyl)-3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]thioxomethyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (DACD) was synthesized from 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[7-(mercapto) thioxomethyl-[3,7-dia zabicyclo[3.3.0]oct-1(5)-en-3-yl}]-4-oxo-3-quinoline carboxylic acid disodium salt(C2) and cefotaxime. The invitro activity of novel dual-action cephalosporin, DACD, was compared with the in vitro activities of CENO(cefotaxime 3'-norfloxacin dithiocarbamate), cefotaxime, and norfloxacin against a variety of bacterial species. In vitro activity of DACD was superior to that of norfloxacin against Streptococcus pyogenes. Against Gram-positive and Gram-negative bacteria, its activity was almost equal to that of CENO.

• 농약과학회지
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• 제4권2호
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• pp.69-71
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• 2000

5-(2,3-dihydro-2,2-dimethylbenzothiophene-7-yl)-2-(1-(alkoxyimino)butyl)-3-hydroxy-2-cyclohexene-1-one 유도체중 azomethine 질소 원자상 alkoxy (RO)-기들이 변화함에 따른 논과 밭 조건에서 살초활성을 측정하고 기질분자(S)의 구조와 살초 활성과의 관계 (SAR)를 검토하였다. 특히, i-propoxy-치환체, 5는 4kg/ha의 농도에서 발아전에 벼(Oryza sativa)에는 아무런 살초효과가 나타나지 않는 반면에 논피 (Echinochloa crus-galli)에만 살초효과가 보이는 선택성을 확인할 수 있었다. SAR분석 결과, 살초활성은 전자효과 (${\sigma}^*$)가 소수성 (logp)보다 2:1의 비율로 큰 영향을 미친다는 사실을 알았으며 이 같은 근거에 따라 alkoxy-기는 강한 전자밀게 (${\sigma}^*<0$)이고 소수성이 큰 (logp>0) alkyl기로 대체되어야 살초활성이 개선될 것으로 판단되었다.

• 약학회지
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• 제31권1호
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• pp.14-18
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• 1987

2-Substituted-3, 4-dihydro-2H-1, 2-benzothiazin-4-one 1, 1-dioxide 6 was reatced with magnesium methyl carbonate to form magnesium chelate 7, which could be hydrolized in cold hydrochloric acid solution to give 2-substituted-4-hydroxy-2H, 1, 2-benzothiazine-3-Carboxylic acid 1, 1-dioxide 2 in good yield.

• Bulletin of the Korean Chemical Society
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• 제9권6호
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• pp.359-362
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• 1988

The condensation of 1-amino-1,2-dihydro-3,6-pyridazinedione (1) and 2-amino-2,3-dihydro-1,4-phthalazinedione (2) with 1,3-diketones or 1,3-dialdehydes in polyphosphoric acid gave 6,9-dihydro-6,9-dioxopyridazino [1,2-a][1,2,3]triazines (3-6) and 6,11-dihydro-6,11-dioxo[1,2,3]triazino[1,2-b]phtha lazines (7-10), respectively. The condensation of 2 with 2,4-pentanedione in acetic acid gave N-alkylidene intermediate (11), which was cyclized to 9 by treatment with polyphosphoric acid.

• 농약과학회지
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• 제5권3호
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• pp.12-17
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• 2001

5-Benzofuryl-2-[1-(alkoxyimine) alkyl]-3-hydroxycyclohex-2-en-1-one 유도체중에서 2,3-dihydro-2,3,4,6,7-penta-methylbenzofuran-5-yl 그룹이 치완된 화합물(III)들의 벼(직파 및 3엽기)와 강피(Echinochloa crus-galli)에 대한 제초활성을 측정하고 alkoxy-치환체($OR_2$)가 변화함에 따른 구조와 제초활성과의 관계(SAR)를 정량적으로 검토한 결과, 직파벼와 강피 사이의 선택성 조건은 $R_1$=ethyl-이고 $R_2$-기는 비 대칭성의 적정값$(L/B_1)_{opt.}=3.96{\AA}$에 가까운 값을 갖는 치환체 이어야 할 것으로 판단되었다. 그리고 Free-Wilson 분석에 따르면 $R_2$-기는 $C_1{\sim}C_3$의 주로 불포화된 것들 중에서 특히, 3-chloro-2-propenyl기가 강피에 대한 제초활성을 가장 크게 나타내었다.

• 대한화학회지
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• 제40권7호
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• pp.526-530
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• 1996

3-Imino-1, 2, 5-thiadiazolidine 1, 1-dioxide와alkylamine 의 반응에 의하여 3-(N-alkylamino)-4, 5-dihydro-1, 2, 5-thiadiazole 1, 1-dioxide를 제조하였다. 이 헤테로고리 화합물의 주요 분광학적 성질과 X-선 결정학외절에 의한 분자구조를밝혔다. 3-(N-benzylamino)-4, 5-dihydro-4-(4'-methoxyphenyl)-1, 2, 5-thiadiazole 1, 1-dioxide의 단결정은 단사정계, 공간군은 $P2_1a$, $a=22.512(3)(1)\AA$, $b=9.831(2)\AA$, $c=7.194(4)\AA$, $\beta=96.65(2)$, 그리고 Z=4이다.