Chemistry Reference
In-Depth Information
O
O
O
5
HN
NH
HN
NH
NH
2
NH
2
NH
2
NH
2
pentamidine (
71
)
phenamidine (
70
)
O
RN
NR
NH
2
NH
2
souamidine (
72
): R = H
pafuramidine (
73
): R = OMe
Figure 10.16
Structures of phenamidine (70) and related compounds
is currently still the clinical drug of choice against African trypanosomiasis, antimony
resistant leishmaniais and Pneumocystis carinii pneumonia (PCP) [103]. This compound
was supposed to show inhibitory activity with insertion into the double helix of DNA [104]
and tRNA [105] and was found to inhibit the RNA function [106]. Recently, souamidine
(72) and the corresponding methoxime pafuramidine (73) are currently in clinical trials for
treatment of African Sleeping sickness, malaria, PCP and Pneumocystis jiroveci pneumonia
[107] (Figure 10.16).
References
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Chemie Organischer Naturstoffe, 66, 119-295.
2. Berlinck, R.G.S. (1996) Natural guanidine derivatives. Natural Product Reports, 13, 377-409.
3. Berlinck, R.G.S. (1999) Natural guanidine derivatives. Natural Product Reports, 16, 339-365.
4. Berlinck, R.G.S. (2002) Natural guanidine derivatives. Natural Product Reports, 19, 617-649.
5. Berlinck, R.G.S. and Kossuga, M.H. (2005) Natural guanidine derivatives. Natural Product
Reports, 22, 516-550.
6. Kobayashi, J. and Ishibashi, M. (1992) Marine Alkaloids II, in The Alkaloids (eds A. Brossi and
G.A. Cordell), 41, 41-124.
7. Kobayashi, J. and Ishibashi, M. (1999) Marine natural products and marine chemical ecology,
in Comprehensive Natural Products Chemistry (eds D. Barton and K. Nakanishi),
8,
415-649.
8. Fattorusso E. and Taglialatela-Scafati O. (eds) (2007) Modern Alkaloids, Wiley-VCH Verlag
GmbH, Weinheim.
9. Greenhill, J.V. and Lue, P. (1993) Amidines and guanidines in medicinal chemistry. Progress in
Medicinal Chemistry, 30, 203-326.
10. Nakamura, S. and Umezawa, H. (1966) The structure of bottromycin A2, a new component of
bottromycins. Chemical & Pharmaceutical Bulletin, 14, 981-986.
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