• The Korean Journal of Pesticide Science
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• v.13 no.2
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• pp.63-69
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• 2009

New morpholinylcarbonylmethyl-2-phenylimino-1,3-thiazolines 2(X=O) and piperidinylcarbonylmethyl-2-phenylimino-1,3-thiazolines 3(X=C) to which morpholinyl or piperidinyl functional group were introduced at C-4 side chain of the 2-phenylimino-1,3-thiazoline scaffold were synthesized to investigate the effect of NH hydrogen of 2-phenylimino-1,3-thiazoline-4-acetanilide derivatives on the antifungal property against rice blast. Synthesized 30 compounds were screened against 6 kinds of typical plant fungi. Treatment of ketene dimer with chlorine followed by the reaction of morphorine or piperidine without isolation of the intermediate acetoacetylchloride gave $\gamma$-chloro-$\beta$-keto derivatives. These were reacted with thioureas to give morpholinylcarbonylmethyl-2-phenylimino-1,3-thiazolines and piperidinylcarbonylmethyl-2-phenylimino-1,3-thiazolines respectively in good yield (27-98%). The compound 3j, in which two fluorine atoms are substituted at ortho and para position of phenyl group of 2-phenylimino moiety and piperidinyl group is substituted at C-4, showed the highest antifungal activity (100 ppm, 90%). This result suggested that the substituent at C-4 of the 2-phenylimino-1,3-thiazolines may play a supplementary role to show the antifungal activity against rice blast.

• Archives of Pharmacal Research
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• v.24 no.1
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• pp.27-34
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• 2001

A series of 2-methylbenzimidazole incorporated to different heterocycles through ethyl or carbamoylethyl groups at position 1 of benzimidazole were synthesized. Also 3-(2-methylbenzimidazol-1-yl)propanoic acid hydrazide incorporated with semicarbazides and thiosemicarbazides were prepared. Moreover, the triazole 5e underwent Michael addition and alkylation reaction. Some of the newly synthesized compounds showed considerable antimicrobial activity against gram positive, negative bacteria and yeast.

• 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.

• Applied Biological Chemistry
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• v.47 no.1
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• pp.154-156
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• 2004

• Bulletin of the Korean Chemical Society
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• v.30 no.8
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• pp.1743-1748
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• 2009

Novel 2-aminothiazolinium based tripodal receptors were designed and synthesized. The binding property of these receptors toward various anions was investigated by the isothermal titration calorimetry (ITC) method. Receptor 4 recognized the acetate anion with 1:1 stoichiometry, whereas it bound the other oxoanions such as sulfate and phosphate in complex modes. By modifying the phenyl groups at the 4-position of the thiazoline rings of the tripodal receptor 4 to induce a mutual aromatic stacking interaction among the three ligands, receptor 10 showed totally different binding behavior, which gave rise to the 1:1 binding mode for the sulfate anion. This result was confirmed by ESI MS spectrometry.

• Journal of Life Science
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• v.18 no.11
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• pp.1570-1577
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• 2008

For useful basic data in developing of Omandungi (Styela plicata) processed products, volatile flavor compounds were analyzed to identify the key reaction flavor compounds induced through heat treatment ($100^{\circ}C$, 10 min) in Omandungi -Doenjang (soybean paste) soups and stew. A total of 128 flavor compounds were identified and composed mainly of esters (16), aromatic compounds (14), N-containing compounds (11), alcohols (34), terpenes (5), carbonyl compounds (23), furans (4), hydrocarbons (13), acids (5) and miscellaneous compounds (3). Three groups including aromatic compounds, alcohols and acids were detected in high amounts in Doenjang. However, the levels of C4-C6 series acids (i.e., pentanoic acid having off-flavor) decreased by cooking ($100^{\circ}C$, 10 min), whereas that of furans (i.e., furfural) as heat induced compounds increased 2 times. Alcohols were detected the major group in Omandungi and followed by hydrocarbons and aromatic compounds in that order. In particular, 3 compounds including decenol, 2,6-dimethylheptanol and octanol were the major alcohols of Omandungi. By cooking, the compounds known heat-induced compound, 2-acetyl-2-thiazoline and benzothiazole, were newly formed in Omandungi-Doenjang stew. The alcohols (i.e., decenol, 2,6-dimethylheptanol), hydrocarbons and aromatic compounds derived from Omandungi were supposed to enhance a seafood-like flavor in Omandungi-Doenjang stew.

• Bulletin of the Korean Chemical Society
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• v.33 no.9
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• pp.2985-2990
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• 2012

New thiazoline derivatives 7a-c, and thiophenes 9a-c linked to indole moiety were easily prepared via the reaction of the acrylamide derivative 3 with phenacyl bromides 4a-c, depending on the reaction conditions. In addition, the reaction of compound 3 with hydrazonoyl chlorides 11a-f afforded a series of 1,3,4-thiadiazole derivatives 13a-f. Moreover, coupling of 3-(3-methyl-1H-indol-2-yl)-3-oxopropanenitrile (2) with the diazonium salts of 3-phenyl-5-aminopyrazole 16 or 3-amino-1,2,4-triazole 17 gave the corresponding hydrazones 18 and 19, respectively. Cyclization of the latter hydrazones yielded the corresponding pyrazolo[5,1-c]-1,2,4-triazine and 1,2,4-triazolo[5,1-c]-1,2,4-triazine derivatives 20 and 21, respectively. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, $^1H$ NMR and mass spectral data. All the synthesized compounds were tested for in vitro activities against certain strains of fungi such as Aspergillus niger, Aspergillus nodulans, Alternaria alternate. Compounds showed marked inhibition of fungal growth nearly equal to the standards.

• Natural Product Sciences
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• v.26 no.3
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• pp.244-251
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• 2020

This study investigated therapeutic candidates with anti-inflammatory potential among traditional dietary ingredients targeting inflammatory bowel disease (IBD). Both Avena sativa and traditional fermented products, such as Korean soy paste, are popular health foods. We investigated the anti-inflammatory effects of soy paste combined with A. sativa (KDA), compared with soy paste without A. sativa (KD) by evaluating the expression of pro-inflammatory cytokines in lipopolysaccharide-stimulated RAW264.7 mouse macrophages and HT-29 human colon epithelial cells. KDA significantly inhibited the production of nitric oxide (NO) and downregulated the pro-inflammatory cytokines, such as interleukin (IL)-1β, IL-6, and tumor necrosis factor-α in lipopolysaccharide (LPS)-induced RAW264.7 cells. In another in vitro experiment involving LPS-stimulated HT-29 cells, KDA suppressed the levels of IL-8, which is the chemokine elevated in IBD. In addition, KDA exhibited anti-oxidative properties, such as 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) and 2,2'-azino-bis(3-ethylbenz-thiazoline-6-sulfonic acid) (ABTS) radical scavenging activity. Our findings revealed that A. sativa combined with soy paste exhibits a synergistic anti-inflammatory and anti-oxidant effect following fermentation. These results suggest that KDA may be used as a potential anti-inflammatory therapy against IBD.

• Journal of Microbiology and Biotechnology
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• v.1 no.1
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• pp.50-53
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• 1991

The reaction steps involved in the bioconversion of a chemically synthesized precursor, $D,L-2-amino-{\Delta}^2-thiazoline-4-carboxylic$ acid (D,L-ATC), to L-cysteine and the properties of the involved enzymes were investigated. It was found that the conversion consisted of two steps, i. e., D,L-ATC to S-carbamyl-L-cysteine (S-C-L-cysteine) and S-C-L-cysteine to L-cysteine, and the S-C-L-cysteine was an intermediate between them. While the enzymes involved in the reactions were induced by the addition of D,L-ATC as an inducer, S-C-L-cysteine induced only the enzyme involved in the latter step. The conversion of S-C-L-cysteine to L-cysteine could be also carried out in the presence of hydroxylamine and its rate was much faster than that by the corresponding enzyme. On the other hand, L-cysteine (or L-cystine) was decomposed to evolve $H_2S$ by the enzyme considered to be a kind of desulfhydrase. However, hydroxylamine was a perfect inhibitor for this enzyme.

• Korean Journal of Fisheries and Aquatic Sciences
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• v.41 no.6
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• pp.414-418
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• 2008

Volatile compounds in Omangdungi (Styela plicata)-Doenjang (soybean paste) stew were analyzed using solvent-assisted flavor evaporation/gas chromatography/mass-selective detection/olfactometry (SAFE/GC/MSD/O) and aroma extract dilution analysis (AEDA). The GC/O analysis detected 37 volatile compounds, of which 32 were positively identified, and included 9 aldehydes, 5 alcohols, 4 aromatic hydrocarbons, 4 ketones, 3 esters, 3 N-containing compounds, 2 acids, 1 S-containing compound, and 1 furan. Nine aroma-active odorants ($\log_3FD{\geq}3.0$) in the sample included six compounds derived from Doenjang (3-methyl(thio)propanal, tetramethylpyrazine, 4-vinyl-2-methoxyphenol, 2-acetylpyrrole, butyric acid, and 2-methoxyphenol) and three compounds from Omangdungi (2-acetyl-2-thiazoline, 9-decanol, and 6-decenol). Three compounds derived from Omangdungi (9-decanol, 6-decenol, and 6-nonenol) were thought to enhance the seafood-like flavor of Omangdungi-Doenjang stew.