P. Parthiban et al. / Bioorg. Med. Chem. Lett. 19 (2009) 2981–2985
2985
Table 2
groups at C-3 and/or C-5 positions play a significant role in eliciting
good antimicrobial properties. Hence, these classes of oxime ethers
can be used as sketch to conquer both bacterial and fungal
infections.
Antifungal activity of compounds 5a–o, 7a–e and 11a–12c
Compds
Minimum inhibitory concentration (lg/mL)
C.
Candida-
51
Rhizopus
sp.
A.
niger
A.
flavus
C.
albicans
neoformans
Acknowledgments
5a
5b
5c
5d
200
100
100
50
50
50
100
50
25
25
200
50
50
100
25
12.5
100
100
50
12.5
25
6.25
50
>200
100
200
50
200
200
100
200
100
50
100
200
50
25
100
50
6.25
50
>200
200
50
>200
200
50
200
200
100
100
50
200
100
>200
200
100
200
>200
200
50
>200
>200
200
100
100
100
200
100
50
The authors would like to acknowledge NMR research center,
IISc-Bangalore and Department of Chemistry, IIT-Madras, respec-
tively, for recording NMR and single crystal XRD. We extend our
thanks to RMMCH, Annamalai University for the antimicrobial
studies.
50
5e
200
100
50
>200
100
50
100
25
12.5
50
25
25
200
100
50
25
50
25
25
200
50
>200
50
50
25
5f1
5f2
5g
5h
5i
5j
5k
5l
5m
5n
50
25
25
25
Supplementary data
200
100
50
100
50
100
100
25
100
50
100
200
100
50
25
50
25
100
>200
100
100
100
25
200
100
50
100
25
12.5
100
50
Complete experimental details, analytical, IR, mass and NMR
data of all compounds. Conformation of alkyl group at C-3 of 5b–
d, 5h, 5k, 5n and 7a–b. Crystal data for 5b and 12a. Supplementary
crystallographic data for 5b (CCDC No. 717888) and 12a (CCDC No.
article can be found, in the online version, at doi:10.1016/
12.5
6.25
100
100
50
5o
7a
7b
25
200
200
100
50
50
50
50
100
50
200
100
25
7c1
7c2
7d1
7d2
7e
11a
11b
12a
12b
12c
Stda
25
12.5
50
25
50
6.25
12.5
200
100
>200
200
25
25
6.25
>200
200
200
50
References and notes
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against Candida-51 and Rhizopus sp. inhibit the visible growth of
fungi at 50 g/mL. Compounds 5g, 5j and 5m show better MICs
while incorporating methyl at C-3 (compounds 5h, 5k and 5n)
and C-5 (compounds 5i, 5l and 5o). Among those, 5l and 5o are
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l
both register their best MIC at 6.25
Pyran analogs 5b and 5c, that is, compounds 7a and 7b show
activity in the range of 50–200 g/mL. The para substitution along
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lg/mL against Candida-51.
l
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1:1, flow rate: 3.5 mL/min..
tested pathogens. In specific, the Me substitution at C-20000 and C-
60000 show better MICs than others; of the two isomers 7d1 and
7d2, the isomer with chair conformation 7d2 is potent than 7d1.
Compounds 7d2 and 7e show remarkable MIC at 6.25 lg/mL
against C. albicans, Candida-51 and C. neoformans, respectively.
Both stereomers 11a and 12a have no activity against most of
the tested pathogenic fungi whereas the introduction of methyl
group at C-20000 and C-60000 of 11a and 12a show better activity
against all the strains. Of the two, trans-isomer 12b is more potent
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the MICs of the trans-isomer 12c are considerably better; espe-
cially 12c register its best MIC at 12.5 lg/mL against C. neoformans,
which is respectively two- and eightfold better than standard and
5m.
In overall, the hetero atom of synthesized compounds paved by
chloro/methyl/methoxy-phenyl on either side along with alkyl