• Title/Summary/Keyword: 1%2C3-thiazole

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Synthesis, Anthelmintic and Anti-inflammatory Activities of Some Novel Imidazothiazole Sulfides and Sulfones

  • Shetty, Nitinkumar S.;Khazi, Imtiyaz Ahmed M.;Ahn, Chul-Jin
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2337-2340
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    • 2010
  • A series of new 6-aryl-3-(3,4-dimethoxy-phenyl)-2-phenylsulfanyl-imidazo[2,1-b]-thiazole (5a-c) and 6-aryl-2-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)imidazo[2,1-b]- thiazole (6a-c) have been prepared and characterized by analytical and spectral methods. The title compounds 5a-c and 6a-c were obtained by the reaction of 4-(3,4-dimethoxy-phenyl)-5-phenylsulfanyl-thiazol-2-ylamine (3) and 5-benzenesulfonyl-4-(3,4-dimethoxy -phenyl)thiazol-2-ylamine (4) with various phenacyl bromides in anhydrous ethanol. These newly synthesized compounds (5a-c and 6a-c) were screened for their anthelmintic and anti-inflammatory activities, where they have displayed better activities.

Synthesis of New 2,4-Diimino-1,3-thiazoles and the Structure Determination (새로운 2,4-Diimino-1,3-thiazoles 유도체의 합성과 구조 결정)

  • Hoh-Gyu Hahn;Chul-soo Lim;Heduck Mah
    • Journal of the Korean Chemical Society
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    • v.47 no.1
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    • pp.38-42
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    • 2003
  • For the purpose of developing new agrochemical fungicides, compound 2 possessing 1,3-thiazole scaffold as well as urea moiety in the structure was designed through molecular modification of lead compound, 2-imino-1,3-thiazoline based on isosterism. The reaction of N-methylthiouea 5 and bromoacetonitrile in ethanol gave 2,4-diimino-1,3-thiazole 4 regioselectively, which was treated with phenyl isocyanates to give the corresponding 7 which is tautomer of 2. The structural assignment of 7 was confirmed by various spectra($^1H$ NMR, $^{13}C$ NMR, FT-IR, HRMS), and X-ray crystallographic data. Compound 8 which is a structural isomer of 7 was formed through thermodynamically unstable intermediate 2,4-diimino-1,3-thiazole 6.

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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    • v.13 no.3
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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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Thiazole Type Accelerator Effects on Silane/Silica Filled Natural Rubber Compound upon Vulcanization and Mechanical Properties (Thiazole계 가황촉진제가 실란/실리카 충전 천연고무 컴파운드의 가황 거동 및 기계적 물성에 미치는 영향)

  • Kim, Sung-Min;Kim, Kwang-Jea
    • Polymer(Korea)
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    • v.36 no.2
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    • pp.235-244
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    • 2012
  • A thiazole type accelerator MBT (2-mercapto benzothiazole) was added into silica filled natural rubber (NR) compound with various concentrations (0, 1, 2, 3, 4 phr). The effects of MBT on the cure rate, mechanical property, degree of rubber-filler interaction (${\alpha}_F$), crosslinking density, and viscoelastic property ($tan{\delta}$) were investigated. As accelerator concentration increased, the $t_{s2}$ and $t_{90}$ decreased and the crosslinking density and modulus at 300% elongation increased. The tensile strength and elongation increased up to 3 phr and no further increased at 4 phr. The $tan{\delta}$ value measured at room temperature was higher than that of the $70^{\circ}C$. The ${\alpha}_F$ value was not affected by the addition of MBT. The mechanisms for the vulcanization rate were reviewed.

Manufacturing of Meat Flavor Extract used for Browning Reaction (Browning Reaction을 이용한 Meat Flavor Extract의 개발)

  • Kim Duk-Sook;Kim Jong-Seung
    • The Korean Journal of Food And Nutrition
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    • v.17 no.3
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    • pp.313-321
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    • 2004
  • Separation-concentration of sulfur containing heterocyclic compounds(SCHC) from many reaction meat flavors manufactured with Maillard reaction was carried out. Profile of SCHC was identified and analyzed by GC and GC-MSD. The results were as follows. 1. Profile of SCHC could be identified 7 kinds thiazole and 11 kinds thiophene, the major produced compounds were thiophene, thiazolidine, 4-methyl-5-thiazole ethanol. 2. In the case of SCHC, relationship between changes of reaction conditions and the kind of produced components were as same, but produced amounts appeared the difference. Producing amount of complexed SCHC and caramellike note as well as oxygen containing heterocyclic compounds were high level more than high reaction temperature and long time reaction period. 3. Producing ratio of comparative simple structural SCHC were the highest level at reaction conditions of moisture content 50%, reaction temperature 100$^{\circ}C$ and reaction time 2 hours. Reaction conditions for the revelation of reaction meat flavor were below 110$^{\circ}C$ and less than 2 hours. 4. Relationship between moisture content and reaction temperature as well as reaction time had very relative relation. From the change of moisture content and reaction conditions could be obtained the simultaneously profile. Signal presentation for production of reaction meat flavor could be from extraction-separation-concentration of SCHC through simplification of raw-materials in the flavor and seasoning food industry.

Heterocyclic Synthesis with Nitriles: New Routes for Synthesis of Pyridazines, Pyridines and their Fused Derivtives

  • Negm, Abdalla-M.;Abdelrazek, Fathy-M.;Elnagdi, Mohamed-H.;Shaaban, Lina-H.
    • Archives of Pharmacal Research
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    • v.17 no.6
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    • pp.411-414
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    • 1994
  • Phenylazocyanothioacetamide 1 reacts with malononitrile to afford the pyridinethione 4 which reacts with phenacylbromide to yield the pyridine-S-phenacyl derivative 6, 1 reacts with ethyl cyanoacetate to yield the pyridazine derivative, 8, and with phenacyl bromide to afford the N-phenacyl derivative 11, instead of the thiazole 10. Compound 11 afforded the pyrazolopyridine 13 on reaction with malononitrile while 10 was obtained on coupling of the thiazole 14 with diazotised aniline. Compound 10 reacts with malononitrile to afford the thizaolyl pyridazine 15. Compound 1 reacts with malononitrile dimer to afford the pyriodopyridazine derivative 17a. 1 reacts also with active methylene heterocycies to afford the pyrazolo and thiazolo-fused phridazines 20 and 23 respectively.

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New Thiazolo[3,2-b][1,2,4]triazole Derivatives : Useful Compounds for the Preparation of 7-Substituted Cephalosporins

  • Nam, Ghil-Soo;Lee, Jae-Chul;Chi, Dae-Yoon;Kim, Joong-Hyup
    • Bulletin of the Korean Chemical Society
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    • v.11 no.5
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    • pp.383-386
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    • 1990
  • We have synthesized several bicyclic heteroaromatic compounds with bridgehead nitrogen from N-amine salts of heteroaromatic amines. 2-Amino and 2-unsubstituted thiazolo[3,2-b][l,2,4]triazole derivatives 2a-b were prepared by the cyclization reaction from N-amine salts of aminothiazole-5-yl(N-methoxyimino)acetate with cyanogen bromide and formamidine acetic acid salt, respectively. 2-Methylthiazolo[3,2-b][1,2,4]triazole 2c was obtained from N-acetylated N-amine salt of aminothiazole-5-yl(N-methoxyimino)acetate by the cyclization reaction in the presence of polyphosphoric acid (PPA). 2-Substituted and 2-unsubstituted thiazole[3,2-b][1,2,4]triazole derivatives 2a-c were coupled with 7-aminocephalosporanic acid (7-ACA). Coupled cephalosporin derivatives 1a-c did not have good antibacterial activities in vitro.

Reactivity of the Biheterocyclic Betaine with the para-Substituted Phenacyl Bromides for the Ring Transformation Reaction

  • Yoo, Kyung-Ho;Kim, Dong-Jin;Kim, You-Seung;Park, Sang-Woo
    • Bulletin of the Korean Chemical Society
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    • v.9 no.3
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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.

Studies on the Characteristics of Humic Acid and Its Utilization (V). Manufacturing of Sulfur-dyes from Humic Acid (土炭흄산의 性狀 및 應用에 關한 硏究(第 5 報). 황化染料 製造)

  • Han Kyoungsuk;Kim Wontaik
    • Journal of the Korean Chemical Society
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    • v.19 no.1
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    • pp.65-70
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    • 1975
  • Sulfur-dyes were manufactured from humic acid, $Na_2S_{2~3}$ and other additives at $200{\sim}250^{\circ}C$ for 3∼20 hrs. Sulfur-dyes from humic acid were fundamentally brown colors and could be changed from yellowish to grayish brown according to the additives. The colorfastness to rubbing and laundering were excellent but to weather was fair. Characteristic bonds of sulfur-dyes such as -C-S-C, -C-SO-C-. -C-$SO_2$-C-, and -C-O-$SO_2$-O-C- were confirmed but thiazole bond and thiazine ring were not done by IR-spectroscopy.

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Comparison of Volatile Flavor Compounds of Domestic Onions (Allium cepa) during Storage (국내산 양파의 저장 중 휘발성 향기성분 비교)

  • Lee, Hee-Young;Jeong, Eun-Jeong;Jeon, Seon-Young;Cha, Yong-Jun
    • Journal of Life Science
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    • v.18 no.12
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    • pp.1712-1717
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    • 2008
  • Volatile flavor compounds of onions were analyzed and compared during storage at $0.5^{\circ}C$, which harvested in 6 regions, such as Muan, Buan, Andong and 3 regions of Changnyeong (Yueo, Jangma and Seongsan). A total of 45 compounds were detected in samples by solid phase microextraction (SPME)/GC/MSD, consisting mainly of sulfur-containing compounds (21), aldehydes (13), ketones (2) and miscellaneous compounds (9). The sulfur-containing compounds were major compounds with ranges of $66.9{\sim}86.9%$ of total volatiles in 0 day of storage as regardless of harvested regions. Three regions (Yueo, Seongsan and Muan) had high amounts of over 4,043 ng/g in 0 day of storage, whereas 2 regions (Muan and Yueo) only had amounts of over 2,400 ng/g after 60 days of storage. Five sulfur-containing compounds known as having antioxidant activity (2,4-, 2,5-dimetylthiophene, 2-vinyl-1,3-dithiane, 5-methoxy thiazole and 3,5-diethyl-1,2,4-trithiolane and isomer) were the high levels in 3 regions (Yueo, Seongsan and Muan) during 60 day of storage. These 3 regions had also the highest amounts in 5 sulfur-containing compounds known as having anticarcinogenic activity ((Z)-, (E)-methyl propenyl disulfide, (Z)-, (E)-propenyl propyl disulfide, and di-2-propenyl disulfide) and kept same trend after 60 days of storage.