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Evaluation of bactericidal and fungicidal activity of ferrocenyl or phenyl derivatives...

Ferrocene compounds

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1042<br />

Fe<br />

THF/diethyl ether<br />

Fe<br />

1<br />

26<br />

OH<br />

O(CH 2) 3NMe 2<br />

HO<br />

HOOC<br />

OH<br />

85%<br />

COOH<br />

COOH<br />

HO<br />

OOC<br />

O(CH 2) 3NMe 2H<br />

COOH<br />

COOH<br />

Fe<br />

Fe<br />

THF/diethyl ether<br />

Scheme 5. Synthesis <strong>of</strong> citric salts 26 <strong>and</strong> 27.<br />

27<br />

10<br />

HO<br />

HOOC<br />

84%<br />

O(CH 2) 3NMe 2<br />

O(CH 2) 3NMe 2<br />

COOH<br />

COOH<br />

O(CH 2)3NMe2H<br />

O(CH 2)3NMe2H<br />

OOC<br />

OOC<br />

OH<br />

COOH<br />

Table 1<br />

Minimum inhibit<strong>or</strong>y concentration (MIC) <strong>and</strong> minimum <strong>bactericidal</strong> concentration (MBC) <strong>or</strong> minimum <strong>fungicidal</strong> concentration (MFC), IC50 <strong>and</strong> log Po/w values.<br />

Cpd. Num.<br />

25<br />

R 3<br />

OH O OH O<br />

OH<br />

O<br />

R 2<br />

R 1<br />

O<br />

OH<br />

H<br />

CH3 H<br />

OH N<br />

H3C CH3 Doxycycline<br />

5 R 1 ¼ R 2 ¼ H<br />

R 3 ¼ Fc<br />

17 R 1 ¼ H; R 2 ¼ OH<br />

R 3 ¼ Ph<br />

6 R 1 ¼ H; R 2 ¼ OH<br />

R 3 ¼ Fc<br />

18 R 1 ¼ OH; R 2 ¼ OH<br />

R 3 ¼ Ph<br />

O(CH 2 ) 3 NMe 2<br />

O(CH 2 ) 3 NMe 2<br />

NH 2<br />

M. El Arbi et al. / Journal <strong>of</strong> Organometallic Chemistry 696 (2011) 1038e1048<br />

Pseudomonas<br />

aeruginosa<br />

(mg/mL (mM))<br />

Staphylococcus<br />

aureus (mg/mL (mM))<br />

C<strong>and</strong>ida albicans<br />

(mg/mL (mM))<br />

MIC

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