• 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.

• Bulletin of the Korean Chemical Society
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• v.24 no.4
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• pp.460-466
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• 2003

For the drug master file (DMF) of ketoconazole, four impurities (1-4) contained in ketoconazole were synthesized. During the synthesis of 2, a new synthetic method of 1,4-dihydropyrazine was established. To oxidize the aminoalcohol (2j) to the aminal (2j-1), the standard Swern oxidation condition was modified to mask the nucleophilicity of the amino group temporarily using one equivalent of acetic acid. Derivative 3 was synthesized via regioselective bromination at the 2 position of the 4-aminophenol derivative (3a) using $Br_2$ in the presence of p-TsOH. The etherification of aryl bromide with the phenol derivative (1f) was accomplished by a modification of the general Cu-mediated reaction condition using excess 1f itself as a solvent at elevated temperature (190 ℃).