4th EucheMs chemistry congress

Poster Session 1
s1101
chem. Listy 106, s587–s1425 (2012)
Poster session 1 - organic chemistry
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the SyntheSiS of SuBStituted triAzineS AS
PotentiAL SynthetiC Auxin herBiCideS
w. whittinGhAM 1 , J. BLAnC 1 , C. winn 1
1 Syngenta, Research Chemistry, Bracknell, United Kingdom
Herbicides that act by mimicking the plant hormone auxin
(indole acetic acid) have been known and used for 70 years.
However, only in the last decade has the molecular mechanism of
action of these compounds begun to be understood. In parallel
with this increased knowledge a number of new herbicides of this
class have been launched or entered development. These
compounds have structures based on a pyridine and pyrimidine
core, but there are no reports of synthetic auxins based on
triazines.
We will describe our work to explore the potential of
compounds with a 1,3,5-triazine core to act as synthetic auxins.
Aspects of the design of the compounds will be discussed, as will
a number of synthetic approaches to the desired targets and the
biological results obtained.
Keywords: triazine; herbicide; auxin;
4 th EucheMs chemistry congress
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PoLyAMine ConJuGAteS of SeLeCted SteroLS:
froM deSiGn to AntiMiCroBiAL And
CytotoxiCity teStS
z. wiMMer 1 , n. vidA 2 , L. rArovA 3 , P. drASAr 2 ,
S. forCzeK 1
1 Institute of Experimental Botany CAS, Isotope Laboratory,
Prague 4, Czech Republic
2 Institute of Chemical Technology in Prague, Chemistry of
Natural Compounds, Prague 6, Czech Republic
3 Centre of the Region Hana of the Palacky University, Growth
Regulators, Olomouc, Czech Republic
Several new polyamine conjugates with stigmasterol and
sitosterol were synthesized and subjected to basic antimicrobial
and cytotoxicity tests. Selected sterols were transformed into their
hemiesters with short-chained dicarboxylic acid anhydrides. The
free carboxylic functionality of the sterol hemiesters was activated
and then allowed to react with N-protected polyamines to form
their amide conjugates. Finally, the N-protecting groups were
removed affording the target products, for which their
physico-chemical characteristics were calculated and compared
with the Lipinski [1] and Ghose [2] rules. The conjugates derived
from spermine displayed considerable antimicrobial activity on
Staphylococcus aureus, a gram-positive bacterium at low
concentration (50 mg.mL-1 ), while these compounds were inactive
towards several gram-negative bacteria. The cytotoxic activity
was tested on cells of human T-lymphoblastic leukemia, breast
adenocarcinoma, cervical cancer, and also on normal human
fibroblasts, and the results will be presented in the IC-50 values
indicating the lethal effect of the tested compound to 50 % of the
tumor cells.
Acknowledgment: Thanks are due to the grants P503/11/0616
(GACR), MSM6046137305 (MSMT) and OC10001 (MSMT), a
part of the COST Action CM0804.
references:
1. C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney,
Adv. Drug Deliv. Rev. 46 (2001) 3-26.
2. A. K. Ghose, V. N. Viswanadhan, J. J. Wendoloski,
J. Combin. Chem. 1 (1999) 55-68.
Keywords: conjugation; steroids; amides; antifungal agents;
antitumor agents;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc