Book of Abstracts - Ruhr-Universität Bochum

P-71
ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum
Synthesis of Chromium-Containing Diterpene Analogs
for the Modulation of NOD Proteins
Aroonchai Saiai a , Janna Velder a , Harald Bielig b , Tomas A. Kufer b , Hans-Günther Schmalz* a
a Institute for Organic Chemistry, University of Cologne, Greinstr.4, 50939, Cologne, Germany.
b Institute for Medical Microbiology, Immunology and Hygiene, University of Cologne, Joseph-
Stelzmann-Str.9, Geb.37, 50931, Cologne, Germany. E-mail: asaiai@smail.uni-koeln.de
Polymorphisms in NOD1 and NOD2 are linked to chronic inflammatory barrier diseases such as
asthma, Blau syndrome, early onset sarcodoisis and Crohn’s disease. 1 Many synthetic compounds in
our group are structurally related pseudoterosins which exhibit pronounced analgesic and antiinflammatory
properties were screened. In continuative research, we found that AKS-01 can inhibit
NOD2-mediated NF-KB activation.
To investigate the structure-activity relationships, Cr(CO)3-complexed compounds which structurally
related to AKS-01were synthesized. 2,3
Synthesis and biological evaluation will be presented in details.
References
OMe
H
OMe
Cr(CO) 3
H
N
AKS-01
OMe
Cr(CO) 3
1.(a) P. Hysi, M. Kabesch, M. F. Moffatt, M. Schedel, D. Carr, N. Klopp, A.W. Musk, A. James, G.
Nunez, N. Inohara and W.O. Cookson, Hum mol genet. 2005, 14, 935-941; (b) P. Rosenstiel, A. Till
and S. Schreiber, Microbes and infection. 2007, 9, 648-657.
2. H.-G. Schmalz, S. Siegel and J.W. Bats, Angew. Chem. Int. Ed. 1995, 34, 2383-2385.
3. O. Hoffmann and H.-G. Schmalz, Synlett. 1998, 12, 1426-1428.
129
H
O
OMe
Cr(CO) 3
1 R 1 = H R 2 = H
2 R 1 = F R 2 = H
3 R 1 = Me R 2 = H
4 R 1 = OMe R 2 = H
5 R 1 = CF 3 R 2 =H
6 R 1 = H R 2 = F
7 R 1 = H R 2 = Me
8 R 1 = H R 2 = CF 3
R 1
R 2