• Title/Summary/Keyword: Antifungal compounds

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Synthesis of 1,3-Dioxolan-2-yliden Derivatives and Their Antifungal Activities (1,3-Dioxolan-2-yliden 유도체들의 합성과 항진균 활성)

  • 김영섭;김우정;김범태;박노균;박창식
    • YAKHAK HOEJI
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    • v.43 no.5
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    • pp.566-571
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    • 1999
  • (1H-1,2,4-Triazolyl) methy-4-(sub). phenyl-5-methyl-1,3-dioxolan-2-yliden (3) derivatives were synthesized and tested for their antifungal activities. The designed compounds with a 1,2,4-triazolylmethyl group at the 4-position of 1,3-dioxolan-2-yliden moiety were synthesized by reaction of difluorinated olefins(2) with (2R, 3R)-2-(2,4-dihalophenyl)-1-(1H-1,2,4-triazol-l-yl) butane-2,3-diol (1). These compounds were tested for in vitro antifungal activities against 16 fungi species. The MIC values were determined by the micro broth dilution method. In general, 1,3-dioxolan-2-yliden derivatives showed antifungal activities in vitro. Among them, (4R, 5R)-4-(2,4-difluorophenyl)-5-methyl-2-[1-(3,4-methylenedioxypheny)meth-ylidene)-1,3-dioxolon-4-yl(1H-1,2,4-triazollyl)methane showed superior antifungal activities to fluconazol and ketoconazol.

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Studies on Biological Activity of Wood Extractives(XIV) - Antifungal activity of isoflavonoids -

  • Park, Youngki;Lee, Sung-Suk;Lee, Hak-Ju;Choi, Don-Ha
    • Journal of the Korean Wood Science and Technology
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    • v.31 no.3
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    • pp.70-76
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    • 2003
  • Five isoflavonoids, biochanin A-7-O-β-D-xylopyranosyl-(1⟶6)-β-D-gluco- pyranoside (1), (-)-maackiain (2), calycosin (3), trifolirhizin (4) and genistein (5), were tested for antifungal activity against nine fungi. These compounds were isolated from the wood (compound 1 and 2) and from the bark (compound 3, 4 and 5) of S. japonica. According to the results of antifungal activity test, (-)-maackiain was evaluated as the best antifungal compound among the isolated compounds. In this regard, it could be mentioned that high antifungal activity of S. japonica wood extracts was originated from (-)-maackiain.

Isolation of Bacillus velezensis SSH100-10 with Antifungal Activity from Korean Traditional Soysauce and Characterization of Its Antifungal Compounds (전통재래 간장으로부터 항진균 활성 B. velezensis SSH100-10의 분리와 그 항진균 물질의 특성 구명)

  • Chang, Mi;Moon, Song Hee;Chang, Hae Choon
    • Food Science and Preservation
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    • v.19 no.5
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    • pp.757-766
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    • 2012
  • The SSH100-10 bacterial strain, which exhibits strong antifungal (anti-mold and anti-yeast) activity, was isolated from traditional korean soysauce aged 100 years. The strain was identified as Bacillus velezensis based on Gram-staining, the biochemical properties and 16S rRNA gene sequence determination. B. velezensis SSH100-10 showed strong proteinase activity and NaCl tolerance, but did not produce enterotoxin. Two-antifungal compounds from B. velezensis SSH100-10 were purified using SPE, preparative HPLC, and reverse phase-HPLC. The purified antifungal compounds were identified as $C_{14}$ and $C_{15}$ iturin through MALDI-TOF-MS and amino acid composition analysis. The stability characteristics of the antifungal compounds after temperature, pH, and enzyme treatments suggested that B. velezensis SSH100-10 produced more than two antifungal compounds; pH-stable $C_{14}$ iturin A and $C_{15}$ iturin A, and unidentified pH-unstable compounds. The results suggested that B. velezensis SSH100-10 can be used in soybean fermentation as a starter. Moreover it has potential as a biopreservative in the food and feed industry and as a biocontrol agent in the field of agriculture.

The Synthesis of Ketoconazole Derivatives Using Biological Activity Compounds in Figue as an Antifungal Agents (항진균제로서 무화과 활성물질을 이용한 Ketoconazole 유도체 합성)

  • Ryu, Soung-Ryual
    • Journal of the Korean Applied Science and Technology
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    • v.16 no.4
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    • pp.299-306
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    • 1999
  • For the synthesis of new antifungal agents, We have synthesized four new ketoconazole derivatives were synthesized by the reaction of cis-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1,3-dioxolan-4-yl]methane sulfonate with isolated fig compounds. These compounds were showed strong antifungal activity against C, albicans ATCC 10231. C, utilis. S, cerevisiae ATCC 9763. A and niger ATCC 9029. Among them, sample No.(13) showed potent inhibition activity. Generally, other samples showed biological activity in vitro test. The above results showed the possibility of the development of new antifungal agents.

Allelopathic Effects on Seed Germination and Fungus Growth from the Secreting Substances of Some Plants (수종식물의 분비물질이 종자 발아와 균류 생장에 미치는 알레로파시 효과)

  • 이호준;김용옥;장남기
    • The Korean Journal of Ecology
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    • v.20 no.3
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    • pp.181-189
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    • 1997
  • Phenolic compounds from 7 species of naturalized invader species and Korean wild plants were analyzed by high performance liquid chromatography. Eleven phenolic compounds including benzoic acid were identified. The extract of naturalized plants was significantly more inhibitory to seed germination and seedling growth of the both naturalized and Korean wild plants. The content of total phenolic compounds in each extract were 43.5 mg/l in Ailanthus altissima as the maximum amount and 25.5 mg/l in Phytolacca americana as the minimum. Phytotoxic substances of ethanol extracts was investigated for antifungal activity against 23 selected fungus species. The antifungal activity of Phytolacca americana showed the greatest clear zone of 23 mm in Aspergillus awamori and its activity had an effect against 6 fungus species. Ailanthus altissima formed the greatest clear zone of 26 mm in Erwinia carotovora sub. sp. carotovora and had an effect agsinst 2 fungus species.

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Synthesis and Biological Activity of Geranyloxy Compounds

  • Oh, Hyun-Ju;Oh, In-Kio;Na, Young-Soon;Kim, Myung-Ju;Baek, Seung-Hwa
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.19 no.3
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    • pp.792-796
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    • 2005
  • Disk assays on the compounds (10 and 12) showed both to have antifungal activity against the dermatophytic fungus Trichophyton mentagrophytes ATCC 28185, (1 and 3 mm inhibition zones at $60\;{\mu}g/disc$), but not against the Gram-positive bacterium B. subtilis or the Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa or fungi Cladosporium resinae and Candida albicans. However, the compound (13) did not show against antifungal activity. The geranyloxy compounds (10, 12, and 13) were cytotoxic to P388 murine leukaemia cells ATCC CCL 46 P388D1, ($IC_50$ >6,250 ng/mL at $7.5\;{\mu}g/disc$). These results suggest that The geranyloxy compounds possesses antimicrobial and antitumor activities.

Antifungal Activities of Biorelevant Complexes of Copper(II) with Biosensitive Macrocyclic Ligands

  • Raman N.;Joseph J.;Velan A. Senthil Kumara;Pothiraj C.
    • Mycobiology
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    • v.34 no.4
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    • pp.214-218
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    • 2006
  • Four copper(II) complexes have been prepared using macrocyclic ligands. The macrocyclic ligands have been synthesized by the condensation reaction of diethyl phthalate with Schiff bases derived from o-phenylene diamine and Knoevenagel condensed ${\beta}-ketoanilides$ (obtained by the condensation of acetoacetanilide and substituted benzaldehydes). The ligands and copper complexes have been characterized on the basis of Microanalytical, Mass, UV-Vis., IR and CV spectral studies, as well as conductivity data. On the basis of spectral studies, a square-planar geometry for the copper complexes has been proposed. The in vitro antifungal activities of the compounds were tested against fungi such as Aspergillus niger, Rhizopus stolonifer, Aspergillus flavus, Rhizoctonia bataicola and Candida albicans. All the synthesized copper complexes showed stronger antifungal activities than free ligands. The minimum inhibitory concentrations (MIC) of the copper complexes were found in the range of $8{\sim}28\;{\mu}g/ml$. These compounds represent a novel class of metal-based antifungal agents which provide opportunities for a large number of synthetic variations for modulation of the activities.

Synthesis and antifungal activity of 6-arylthio-/6-arylamino-4,7-dioxobenzothiazoles

  • Han, Ja-Young;Choi, Ik-Hwa;Chae, Mi-Jin;Jung, Ok-Jai;Ryu, Chung-Kyu
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.178.1-178.1
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    • 2003
  • 6-Arylthio-/6-arylamino-4,7-dioxobenzothiazoles were synthesized and tested for in vitro antifungal activity against Candida species and Aspergillus niger. 6-Arylamino-4,7-dioxobenzothiazoles showed, in general, more potent antifungal activity than 6-arylthio-4,7-dioxobenzothiazoles. The 6-arylamino-substituted compounds exhibited the greatest activity. In contrast, 6-arylthio-, 2-/5-methyl-or 5-methoxy-moieties of compounds did not improve their antifungal activity significantly. The results of this study suggest that 6-arylamino-4,7-dioxobenzothiazoles would be potent antifungal agents

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Synthesis and Antifungal Activity of 6,7-Bis-[S-(Aryl)thio]-5,8-Quinolinediones

  • Ryu, Chung-Kyu;Sun, Yang-Jung;Shim, Ju-Yeon;You, Hea-Jung;Choi, Ko-Un;Lee, Hee-Soon
    • Archives of Pharmacal Research
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    • v.25 no.6
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    • pp.795-800
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    • 2002
  • 6,7-Bis-[S-(aryl)thio]-5,8-quinolinediones 4 and 5 were synthesized by the substitution of 6,7-dichloro-5,8-quinolinediones with appropriate arylthiols. Their antifungal activity were tested in vitro for their growth inhibitory activities against pathogenic fungi in comparison with flucytosine. The antifungal activities were significantly improved by S-(aryl)thio moieties of the compounds 4 and 5. The all tested compounds 4 and 5 showed generally good activities against C. albicans and A. niger ranging from 0.8 to 25 $\mu\textrm{g}$/ml. Among them, compounds 4d-4h and 5a-5c exhibited also good activities against C. krusei and C. tropicalis. The activities of compounds 4j and 4I were comparable to those of flucytosine against all tested fungi.

Antibacterial, Antifungal and Anticonvulsant Evaluation of Novel Newly Synthesized 1-[2-(1H-Tetrazol-5-yl)ethyl]-1H-benzo[d][1,2,3]triazoles

  • Rajasekaran, Aiyalu;Murugesan, Sankaranarayanan;AnandaRajagopal, Kalasalingam
    • Archives of Pharmacal Research
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    • v.29 no.7
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    • pp.535-540
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    • 2006
  • Several novel 1-[2-(1H-tetrazol-5-yl) ethyl]-1H-benzo[d][1,2,3]triazoles (3a-h) have been synthesized by the condensation of 1-[2-(1H-tetrazol-5-yl)-ethyl]-1H-benzotriazole (2) and appropriate acid chlorides. 1-[2-(1H-tetrazol-5-yl)-ethyl]-1H-benzotriazole (2) was synthesized by reacting 3-(1H-benzo[d][1,2,3]triazol-1-yl)propanenitrile with sodium azide and ammonium chloride in the presence of dimethylformamide. The synthesized compounds were characterized by IR and PMR analysis. The titled compounds were evaluated for their in vitro antibacterial and antifungal activity by the cup plate method and anticonvulsant activity evaluated by the maximal electroshock induced convulsion method in mice. All synthesized compounds exhibited moderate antibacterial activity against Bacillus subtilis and moderate antifungal activity against Candida albicans. Compounds 5-(2-(1 H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(4-aminophenyl)methanone 3d and 5-(2-(1 H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(2-aminophenyl)methanone 3e elicited excellent anticonvulsant activity.