TY  - JOUR
A1  - Raschig, Martina
A1  - Ramírez‐Zavala, Bernardo
A1  - Wiest, Johannes
A1  - Saedtler, Marco
A1  - Gutmann, Marcus
A1  - Holzgrabe, Ulrike
A1  - Morschhäuser, Joachim
A1  - Meinel, Lorenz
T1  - Azobenzene derivatives with activity against drug‐resistant Candida albicans and Candida auris
JF  - Archiv der Pharmazie
N2  - Increasing resistance against antimycotic drugs challenges anti‐infective therapies today and contributes to the mortality of infections by drug‐resistant Candida species and strains. Therefore, novel antifungal agents are needed. A promising approach in developing new drugs is using naturally occurring molecules as lead structures. In this work, 4,4'‐dihydroxyazobenzene, a compound structurally related to antifungal stilbene derivatives and present in Agaricus xanthodermus (yellow stainer), served as a starting point for the synthesis of five azobenzene derivatives. These compounds prevented the growth of both fluconazole‐susceptible and fluconazole‐resistant Candida albicans and Candida auris strains. Further in vivo studies are required to confirm the potential therapeutic value of these compounds.
KW  - antifungal drug
KW  - azobenzenes
KW  - Candida auris
KW  - Candida albicans
Y1  - 2023
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-312295
VL  - 356
IS  - 2
ER  - 
TY  - JOUR
A1  - Scheiner, Matthias
A1  - Sink, Alexandra
A1  - Spatz, Philipp
A1  - Endres, Erik
A1  - Decker, Michael
T1  - Photopharmacology on Acetylcholinesterase: Novel Photoswitchable Inhibitors with Improved Pharmacological Profiles
JF  - ChemPhotoChem
N2  - Considerable effort has previously been invested in a light‐controlled inhibition of the enzyme acetylcholinesterase (AChE). We found that a novel azobenzene‐based bistacrine AChE inhibitor switched faster than the known dithienylethene based bistacrine and inverted the photo‐controlled interactions of the photoisomers compared to its dithienylethene congener. Furthermore, we have optimized a previously described light‐controlled tacrine‐based AChE inhibitor. Isomerization upon irradiation with UV light of the novel inhibitor was observed in aqueous medium and showed no fatigue over several cycles. The cis‐enriched form showed an 8.4‐fold higher inhibition of hAChE compared with its trans‐enriched form and was about 30‐fold more active than the reference compound tacrine with a single‐digit nanomolar inhibition. We went beyond proof‐of‐concept to discover photoswitchable AChE inhibitors with pharmacologically desirable nanomolar inhibition, “cis‐on” effect, and pronounces differences between the photoisomers.
KW  - azobenzenes
KW  - enzymes
KW  - kinetics
KW  - photopharmacology
KW  - tacrine
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-218445
VL  - 5
IS  - 2
SP  - 149
EP  - 159
ER  - 
TY  - JOUR
A1  - Ansell, Melvyn B.
A1  - Kostakis, George E.
A1  - Braunschweig, Holger
A1  - Navarro, Oscar
A1  - Spencer, John
T1  - Synthesis of functionalized hydrazines: facile homogeneous (N-heterocyclic carbene)-palladium(0)-catalyzed diboration and silaboration of azobenzenes
JF  - Advanced Synthesis & Catalysis
N2  - The bis(N-heterocyclic carbene)(diphenylacetylene)palladium complex Pd(ITMe)\(_2\)(PhCCPh)] (ITMe=1,3,4,5-tetramethylimidazol-2-ylidene) acts as a highly active pre-catalyst in the diboration and silaboration of azobenzenes to synthesize a series of novel functionalized hydrazines. The reactions proceed using commercially available diboranes and silaboranes under mild reaction conditions.
KW  - Palladium-catalyzed silaboration
KW  - B-B bond
KW  - molecular-structure
KW  - terminal alkynes
KW  - crystal-structure
KW  - alkenes
KW  - complexes
KW  - mechanism
KW  - boron
KW  - design
KW  - azobenzenes
KW  - dilaboration
KW  - N-heterocyclic carbenes
KW  - palladium
KW  - silaboration
Y1  - 2016
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-186582
VL  - 358
IS  - 23
ER  -