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

Ferrocene compounds

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Table 1 (continued)<br />

Cpd. Num.<br />

R 3<br />

R 2<br />

R1 2 R 1 ¼ OH; R 2 ¼ OH<br />

R 3 ¼ Fc<br />

19 R 1 ¼ H; R 2 ¼ NH2<br />

R 3 ¼ Ph<br />

3 R 1 ¼ H; R 2 ¼ NH2<br />

R 3 ¼ Fc<br />

20 R 1 ¼ H; R 2 ¼ NHAc<br />

R 3 ¼ Ph<br />

4 R 1 ¼ H; R 2 ¼ NHAc<br />

R 3 ¼ Fc<br />

7 R 1 ¼ H; R 2 ¼ NHCOEt<br />

R 3 ¼ Fc<br />

8 R 1 ¼ H;<br />

R 2 ¼ NHCOiPr<br />

R 3 ¼ Fc<br />

9 R 1 ¼ H; R 2 ¼ NHCO t Bu<br />

R 3 ¼ Fc<br />

22 R 1 ¼ OH<br />

R 2 ¼ O(CH2)3NMe2<br />

R 3 ¼ Ph<br />

1 R 1 ¼ OH<br />

R 2 ¼ O(CH2)3NMe2<br />

R 3 ¼ Fc<br />

21 R 1 ¼ O(CH2)3NMe2<br />

R 2 ¼ O(CH2)3NMe2;<br />

R 3 ¼ Ph<br />

10 R 1 ¼ O(CH2)3NMe2<br />

R 2 ¼ O(CH2)3NMe2<br />

R 3 ¼ Fc<br />

11 R 1 ¼ OH<br />

R 2 ¼ O(CH2)4NMe2; R 3 ¼ Fc<br />

12 R 1 ¼ H; R 2 ¼ Br<br />

R 3 ¼ Fc<br />

13 R 1 ¼ H; R 2 ¼ CN<br />

R 3 ¼ Fc (Z isomer)<br />

14 R 1 ¼ OH;<br />

R 2 ¼ OCO t Bu<br />

R 3 ¼ Fc<br />

15 R 1 ¼ OCO t Bu<br />

R 2 ¼ OCO t Bu;<br />

R 3 ¼ Fc<br />

16 R 1 ¼ OCOC15H31<br />

R 2 ¼ OCOC15H31<br />

R 3 ¼ Fc<br />

23 R 1 ¼ OCOC15H31<br />

R 2 ¼ OCOC15H31<br />

R 3 ¼ Ph<br />

26 R 1 ¼ O(CH2)3NMe2H þ<br />

R 2 ¼ OH; R 3 ¼ Fc<br />

27 R 1 ¼ O(CH2)3NMe2H þ<br />

R 2 ¼ O(CH2)3NMe2H þ<br />

R 3 ¼ Fc<br />

HO<br />

24<br />

Fe<br />

a<br />

MFC value; n.tox: non-toxic at 10 mM; nd: not determined.<br />

b<br />

Values from Ref. [45].<br />

c<br />

Values from Ref. [12].<br />

d<br />

Values from Ref. [14].<br />

e<br />

Values from Ref. [47].<br />

f<br />

Values from Ref. [52].<br />

OH<br />

M. El Arbi et al. / Journal <strong>of</strong> Organometallic Chemistry 696 (2011) 1038e1048 1043<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 />

IC50 on MDA-MB-231 (mM) log Po/w<br />

MIC 100 (235.67) 100 (235.67) 100 (235.67) 0.6 c<br />

5.0 c<br />

MBC 200 (471.35) 200 (471.35) 200 a (471.35)<br />

MIC 50 (167) 50 (167) 50 (167) > 1 mM d<br />

4.86 d<br />

MBC 200 (678) 200 (678) 200 a (678)<br />

MIC 25 (61.4) 100 (245.5) 100 (245.5) 0.8 d<br />

5.75 d<br />

MBC 50 (122.7) 200 (491) 200 a (491)<br />

MIC 100 (292.9) 100 (292.9) 100 (292.9) 55.4 e<br />

MBC 200 (585.7) 200 (585.7) 200 a (585.7)<br />

MIC 100 (222.5) 100 (222.5) 100 (222.5) 0.65 d<br />

5.92 d<br />

MBC 200 (445.1) 200 (445.1) 200 a (445.1)<br />

MIC 100 (215.80) 100 (215.80) 100 (215.80) 1.2 5.89<br />

MBC 200 (431.6) 200 (431.6) 200 a (431.6)<br />

MIC 100 (209.5) 100 (209.5) 100 (209.5) 2.02 6.13<br />

MBC 200 (418.9) 200 (418.9) 200 a (418.9)<br />

MIC 100 (203.5) 100 (203.5) 100 (203.5) > 1 mM 6.35<br />

MBC 200 (407) 200 (407) 200 a (407)<br />

MIC

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