• Journal of the Korean Chemical Society
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• v.46 no.4
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• pp.330-336
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• 2002

For the purpose of development of new agrochemical fungicide of ${\alpha},{\beta}-unsaturated$ carboxanilide series a synthesis of 4-acetyl-3-methyl-N-phenyl-1,4-thiazine-2-carboxamide (6) is described. Pummerer reaction of sulfoxide 7 obtained by sulfoxidation of dihydro-1,4-thiazine methyl ester 11 gave ${\alpha}-acetoxy$ dihydro-1,4-thiazine 10a. Under the same reaction conditions, dihydro-1,4-thiazine carboxanilide sulfoxide 14 was converted to acetoxymethyl dihydro-1,4-thiazine 18 through vinylogous Pummerer reaction involving carboxanilide of sulfonium ion through intermediate 15.1,4-Thiazine carboxanilide 6 was synthesized from the treatment of ${\alpha}-acetoxy$ dihydro-1,4-thiazine 10a with acid cat-alyst followed by hydrolysis and then the reaction with aniline.

• The Korean Journal of Pesticide Science
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• v.9 no.2
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• pp.122-131
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• 2005

For development of new agrochemical fungicide, syntheses of pyrrolo[2,1-b]thiazole carboxanilide derivatives 9 and antifungal screening against 6 kinds of plant pathogens were carried out. Functionalization of carboxylic acid on C-2 into carboxanilide in the pyrrolo[2,1-b]thiazole resulted in new 20 candidates, in which are ${\alpha},{\beta}$-unsaturated carboxanilide and methyl groups that are in cis relationship. Treatment of acetoxy-1,4-thiazin with magnesium in refluxing methanol gave pyrrolo[2,1-b]thiazole ethyl ester 4 in higher yield than that of the previous report. Hydrolysis of this compound afforded the corresponding acid 5, which reacted with aniline derivatives in the presence of coupling reagent, DIC to give pyrrolo[2,1-b]thiazole carboxanilides 9. As the result of in vivo antifungal assay of 9 against rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, some compounds showed selectively antifungal activities against the rice blast and wheat leaf rust.

• Archives of Pharmacal Research
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• v.23 no.4
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• pp.315-323
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• 2000

Syntheses of new analogues of oxathiin carboxanilide (UC84) and their antiviral activities were described. The heterocyclic carboxylic acids including oxathiins (4), thiazines (9) and dithiins (13) in which the methyl was replaced either by lipophilic trifluoromethyl- or bulky phenylgroup were synthesized starting from $\beta$-keto esters (5). Reaction of 4, 9 and 13 with thionyl chloride followed by treatment of the substituted aniline 22 gave the corresponding carboxanilides (24a~24f). The carboxanilides were subjected to Laweson's reagent the corresponding thiocarboxanilides (24g~24k). The antiviral activities of the synthesized compounds against human immunodeficiency virus type 1 (HIV-1), poliovirus type 1 (PV-1 ), coxsackie B virus type 3 (CoxB-3), vesicular stomatitis virus (VSV) and herpes simplex virus type 1 (HSV-1) were presented. The antiviral activity against HIV-1 of dithiin carboxanilide (24e) was similar with that of UC84 (24a). The corresponding thiocarboxanilides (24g~24k) showed higher inhibitory activity against HIV-1 than the carboxanilides (24a, 24b, 24d, 24e). The compounds in which ether the lipophilic trifluorormethyl substituents (24d, 24f, 24i ,24k) or bulky phenyl substituent is present in the heterocyclic compounds showed lower inhibitory activity than that of the methyl substituents is present in the compounds against the HIV-1. But the trifluoromethylated dithiin (24f) showed higher inhibitory activity against PV-1 and CoxB-3 virus than commercial antiviral agents, ribavirin (RV).

• Bulletin of the Korean Chemical Society
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• v.20 no.10
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• pp.1218-1220
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• 1999

• Bulletin of the Korean Chemical Society
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• v.22 no.2
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• pp.149-153
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• 2001

A new methodology for construction of dihydro-1,4-dioxin skeleton was described. Introduction of thio group at the ${\alpha}-position$ of 8 followed by chlorination gave 11, which was to prevent an enolization as well as to promote the facile nucleophilic substitution reaction of ethylene glycol giving 16 in equilibrium with cyclic ether 19. Removal of thio group of 19 and dehydration in the presence of an acid catalyst gave dihydro-1,4-dioxin 21. In case of electron withdrawing trifluoromethyl group is subsituted in C-2, 18 was converted to the corresponding dihydro-1,4-dioxin 20 by the halogenation of hydroxy followed by treatment of triethylamine.

• The Korean Journal of Pesticide Science
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• v.2 no.3
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• pp.64-69
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• 1998

New thirty derivatives of 5,6-dihydro-2-trifluoromethyl-1,4-oxathiin carboxanilide as substrate(S) were synthesized and their fungicidal activities in vivo against rice sheath blight(Rhizoctonia solani) and wheat leaf rust(Puccinia recondita) were examined. The structure activity relationships(SAR) between the activities($pI_{50}$) and a physicochemical parameters of substituents(X) at the phenylcarbamoyl group were analyzed using the adaptive regression analysis method. The 3-methoxy, 11, 3-isopropyloxy, 13 and 3-isopropyl substituent, 25 as X on the phenylcarbamoyl group exhibited the most highest fungicidal activity against the two fungi. The fungicidal potency of the (S) against Puccinia recondita was higher than Rhizoctonia solani. In case of Rhizoctonia solani, the molecular hydrophobicity(${\pi}>0$) and resonance effect(R<0) by meta-alkyl substitutents with electron donating were important factors in determining fungicidal activity. And the HOMO energy(HOMO>0), ABSQ, sum of absolute values of the atomic charges on each atom and specific polarizability(Sp.Pol<0) of (S) were significantly influential towards fungicidal activity against Puccinia recondita.. The interaction between (S) and receptor agonist from the based on SAR studies proceeds through charge-control reaction, and conditions to show higher activity has been also discussed.

• Korean Journal of Microbiology
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• v.49 no.1
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• pp.17-23
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• 2013

Candida biofilms are organized microbial communities growing on the surfaces of host tissues or indwelling medical devices, and the biofilms show enhanced resistance against the conventional antifungal agents. The roots of Coptidis chinensis have been widely used for medicinal purposes in East Asia. The present study was aimed to assess the effect of C. chinensis aqueous extract upon preformed biofilms of 10 clinical Candida albicans isolates and the antifungal activities which contribute to inhibit the C. albicans biofilm formation. Its effect on preformed biofilms was judged using XTT [2,3-Bis-(2-Methoxy-4-Nitro-5-Sulfophenyl)-2H-Tetrazolium-5-Carboxanilide)] reduction assay, and metabolic activity of all tested strains was reduced significantly ($57.3{\pm}14.7%$) at $98{\mu}g/ml$ of the C. chinensis extract. The extract damaged the cell membrane of C. albicans which was analyzed by fluorescein diacetate and propidium iodide staining. The anticandidal activity was fungicidal, and the extract obstructed the adhesion of C. albicans biofilms to polystyrene surfaces, arrested C. albicans cells at $G_o/G_1$ as well, and reduced the growth of biofilms or budding yeasts finally. The data suggest that C. chinensis has multiple antifungal effects on target fungi resulting in preventing the formation of biofilms. Therefore, C. chinensis holds great promise for exploring antifungal agents from natural products in treating and eliminating biofilm-associated Candida infection.

• Journal of Veterinary Clinics
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• v.23 no.4
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• pp.411-415
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• 2006

Ascorbic acid has been used widely as a medium supplement to stimulate cell proliferation, but its effects on cell proliferation have not yet been elucidated, and no reports have analyzed effects on subcultured chondrocytes. Subcultured canine chondrocytes of passage one, two and four were cultured in monolayer and alginate beads with and without ascorbic acid. Cell proliferation was examined by 2,3-Bis(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide inner salt) (XTT) colormetric assay. Ascorbic acid stimulated cell proliferation significantly in both culture methods (p<0.05). The increased cell numbers by stimulation with ascorbic acid were significantly high in passage one cells compared to that of other passages. Differences in cell proliferative capacity by subculturing were not determined. These results suggest that ascorbic acid stimulated the proliferation of subcultured canine chondrocytes and enhanced it more in low-passage cells than in the other cells tested.

• The Korean Journal of Pesticide Science
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• v.4 no.2
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• pp.29-31
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• 2000

New convenient and economical synthesis of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide 1 and the plausible reaction mechanism were described. Reaction of ${\alpha}$-chloroacetoacetanilide 4 (1 molar equivalent) with 2-mercaptoethanol (1.2 molar equivalent) in the presence of p-toluenesulfonic acid monohydrate (0.05 molar equivalent) as a catalyst in refluxing toluene with water trap yielded carboxin 1. The proposed mechanism is that ${\alpha}$-chloro 1,3-oxathiolane 8 which is a heuithioketal of 4 was converted to unisolable sulfonium ion 9 through neighboring group participation of sulfur followed by rearrangement to more stable oxonium ion 12 and then release acidic proton to produce the carboxin 1.

• The Journal of Advanced Prosthodontics
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• v.9 no.5
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• pp.335-340
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• 2017

PURPOSE. Bacterial adhesion on provisional crown materials retained for a long time can influence the duration for which permanent prosthetic restorations can be healthily worn in the oral cavity. The aim of this study was to compare seven different commonly used provisional crown materials with regard to Streptococcus mutans and Candida albicans surface adhesion. MATERIALS AND METHODS. For each group, twenty specimens of the provisional fixed prosthodontic materials TemDent ($Sch{\ddot{u}}tz$), Imident (Imicryl), Tab 2000 (Kerr), Structur Premium (Voco), Systemp (Ivoclar Vivadent), Acrytemp (Zhermack), and Takilon-BBF (Takilon) were prepared (diameter, 10.0 mm; height, 2.0 mm). Surface roughness was assessed by atomic force microscopy. Each group was then divided into 2 subgroups (n=10) according to the microbial suspensions used: S. mutans and C. albicans. The specimens were incubated at $37^{\circ}C$ with S. mutans or C. albicans for seven days. Bacterial adherence on surfaces was assessed using the 2,3-bis[2-methyloxy-4-nitro-5-sulfophenyl]-2H-tetrazolium-5-carboxanilide (XTT) assay. RESULTS. S. mutans showed maximum adhesion to Structur, followed by Systemp, Acrytemp, Takilon, Tab 2000, Imident, and TemDent (P<.05). The highest vital C. albicans adhesion was noted on Takilon, followed by Imident and Tab 2000; the lowest adhesion was noted on Systemp (P<.05). CONCLUSION. The materials showed significant differences in the degree of bacterial adhesion. C. albicans showed higher surface adhesion than S. mutans on provisional crown and fixed partial denture denture materials.