• YAKHAK HOEJI
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• v.47 no.5
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• pp.288-292
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• 2003

The synthesis of new 6-exomethylene penams with substituted triazole ring was described. The 6,6-dibromopenam 5 was reacted with $CH_3$MgBr and substituted triazole 4 to afford the 6-bromo penicillanate 6, which was treated with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylene penams 8, which was oxidized to sulfones 9 by m-CPBA. The p-methoxybenzyl compounds 6∼9 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 10∼13.

• YAKHAK HOEJI
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• v.44 no.2
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• pp.128-134
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• 2000

The synthesis of new 6-exomethylene penams with triazole ring was described. The 6,6-dibromopenam 5 was treated with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was reacted with acetic anhydride to give acetoxy compound 7. The deacetobromination of 7 with zinc and acetic acid gave 6-exomethylenpenams, Z-isomer 8 and E-isomer 9, which were oxidized to sulfones 10 and 11 by m-CPBA. The p-methoxybenzyl compounds 6~11 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 12~17.

• YAKHAK HOEJI
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• v.48 no.5
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• pp.303-308
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• 2004

The synthesis of new 6-triazole exomethylenepenams was described. The 6,6-dibromopenam 5 was reacted with $CH_3$MgBr and substituted triazole 4 to afford the 6-bromo penicillanate 6, which was treated with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylene penams 8 and 9, which were oxidized to sulfones 10 and 11 by m-CPBA. The p-methoxybenzyl compounds 6-11 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 12-17.

• YAKHAK HOEJI
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• v.40 no.2
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• pp.131-134
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• 1996

3,4-Dimethoxyphenethyl amine(1) and 3,4-dimethoxybenzaldehyde were converted to compounds(4) through sucessive condensation and reduction reaction. Compound(4) was treated with methylthioacetyl chloride to give compound(5) then m-chloroperbenzoic acid(m-CPBA) treatment of compound(5) produced S-oxide(6). To obtain isoquinoline derivative(7),(8), compound(6) were treated with p-TsOH. Xylopinine(9) and it's derivatives(10) were produced by Bischler-Napieralski reaction.

• YAKHAK HOEJI
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• v.54 no.6
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• pp.466-473
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• 2010

A series of $3{\beta}$-substituted 5-androstene-$17{\beta}$-carboxamides were synthesized from analogs of $3{\beta}$-hydroxy-5-androstene-$17{\beta}$-carboxylic acid (1) with tert-butylamine, N,N-diethylamine and 3-aminopyridine and some compounds were epoxidized with mCPBA. A rat prostate testosterone $5{\alpha}$-reductase inhibitory activity of synthesized compounds was assessed by radioimmunoassay using [1,2,6,7-3H]-testosterone as substrate. All synthesized compounds showed lower activity than finasteride and the N-(3-pyridino)-$3{\beta}$-carboxycarbonyloxy-5-androstene-$17{\beta}$-carboxamide (12) showed weak inhibitory activity ($IC_{50}$: $2.4{\times}10^{-7}M$).

• YAKHAK HOEJI
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• v.46 no.6
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• pp.381-386
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• 2002

The synthesis of new 6-exomethylene sulbactam derivatives with 5-methyl-1,3,4-thiadiazole was described. The 6,6-dibromopenam 5 was reacted with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was treated with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylen penams, Z-isomer 8 and E-isomer 9, which was oxidized to sulfones 10 by m-CPBA. The p-methoxybenzyl compounds 6-10 were deprotected by AlCl$_3$ and neutralized with NaOH solution to give the sodium salts 11-15.

• YAKHAK HOEJI
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• v.52 no.4
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• pp.311-315
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• 2008

The synthesis of 7-arylidene cephalosporanates for ${\beta}-lactamase$ inhibitor was described. The reactions of substituted benzyl halides $[1]{\sim}[3]$ with triphenylphosphine gave triphenylphcsphonium chlorides $[4]{\sim}[6]$. These phosphonium salts were treated with n-butyllithium to give ylides, which were reated with 7-oxocephalosporanate [7] by Wittig reaction to afford the 7-exomethylene cephalosporanates $[8]{\sim}[10]$. These cephalosporanates were oxidized to cephalosporanate sulfones $[11]{\sim}[13]$ with mCPBA. The deprotection of benzhydryl cephalosporanate $[8]{\sim}[13]$ with $AlCl_3$ and $NaHCO_{3}$ gave sodium salts of 7-arylidene cephalosporanates $[14]{\sim}[19]$.

• YAKHAK HOEJI
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• v.45 no.2
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• pp.140-146
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• 2001

The synthesis of new 6-exomethylene penams with triazole ring for $\beta$-lactamase inhibitor was described. The 6,6-dibromopenam 6 was treated with $CH_3$MgBr and carbaldehyde 5 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 7, which was reacted with acetic anhydride to give acetoxy compound 8. The deacetoxybromination of 8 with zinc and acetic acid gave 6-exomethylenepenams, Z-isomer 9 and E-isomer 10, which were oxidized to sulfones 11 and 12 by m-CPBA. The p-methoxybenzyl compounds 9~12 were deprotected by AIC1$_3$and neutralized to give the sodium salts 13~16.

• YAKHAK HOEJI
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• v.46 no.5
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• pp.307-312
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• 2002

The synthesis of new 6-exomethylene penams with benzothiazole ring was described. The 6,6-dibromopenam 5 was treated with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was reacted with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylene penams, Z-isomer 8 and E-isomer 9, which was oxidized to sulfones 10 by m-CPBA. The p-methoxybenzyl compounds 6~10 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 11~15.

• YAKHAK HOEJI
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• v.43 no.6
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• pp.782-788
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• 1999

7-Oxocephalosporanate 1 was treated with phosphonium salts 2~4 by Wittig reaction to afford 7-exomethylene cephalosporanates 5~7. They were oxidized to sulfones 8~10 with mCPBA. Deprotecton of benzhydryl 7-exomethylene cephalosporanate with $AlCl_3$ and NaHCO_3$ gave sodium salts of 7-exomethylene cephalosporanates 11~16. The ${\beta}-lactamase$ inhibitory activity of synthesized compounds 11~16 were compared with sulbactam, tazobactam and clavulanic acid against Type I, II, III, IV and TEM-2 $\beta$-lactamase in vitro. Compound 15 showed more potent activity than sulbactam and clavulanic acid against Type III, IV ${\beta}-lactamase$ enzyme.