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

Fe
NH 2
22 are inactive on hormone-independent MDA-MB-231 breast
cancer cells, while their ferrocenyl analogs 2, 3, 4 and 1 are amongst
the most effective, with IC50 values between 0.5 mM and 0.8 mM.
This difference is confirmed with compound 24, which is very
active on MDA-MB-231 cancer cells, with an IC50 value of 0.09 mM,
R
2
18
Fe
3
R=Fc
R=Ph
OH
OH
2
M. El Arbi et al. / Journal of Organometallic Chemistry 696 (2011) 1038e1048 1041
OH
OH
NaH , THF
1) EtONa, EtOH
2)
Br
RCOCl
Pyridine
Fe
NHCOR
Scheme 3. Synthesis of amido compounds 7, 8 and 9.
R'COCl R
R
14
Br
3
7 R=Et 92%
8 R= iPr 76%
9 R= t Bu 63%
but less active on microorganisms. The only shared characteristic
between P. aeruginosa, S. aureus, C. albicans. and MDA-MB-231
cancer cells seems to be their sensitivity towards compounds
bearing amino alkyl chains. The monoamine compounds 22 and 1
are active on the three microorganisms, with MIC values ranging
O
OH
R'
O
R=Fc; R'=t-Bu 34%
O
R'
R'
O
15
O
R=Fc; R'=t-Bu 28%
23 R=Ph; R'=-(CH2 ) 14CH3 96%
Scheme 4. Synthesis of pivaloate derivatives 14 and 15 and palmitate derivative 23.
Fe
HNMe 2
MeOH
Fe
29
60°C
24 hrs
10
Scheme 2. Synthesis of ferrocenyl diamino compound 10.
O(CH2)3Br
O(CH 2) 3Br
O(CH2)3NMe2
O(CH 2 ) 3 NMe 2
57% overall yield
O