83115-56-4Relevant academic research and scientific papers
Synthesis of Naphthoquinone Antibiotics: Conjugate Addition/Electrophile Trapping with Acylnickel Carbonylate Anions
Semmelhack, M. F.,Keller, Leonard,Sato, Tadahisa,Spiess, E.
, p. 4382 - 4384 (1982)
Conjugate addition of nickel acylate complexes followed by quenching with allyl iodide provide key intermediates for the synthesis of nanomycin A and frenolicin
Rational design of indoleamine 2,3-dioxygenase inhibitors
R?hrig, Ute F.,Awad, Loay,Grosdidier, Aurélien,Larrieu, Pierre,Stroobant, Vincent,Colau, Didier,Cerundolo, Vincenzo,Simpson, Andrew J. G.,Vogel, Pierre,Van Den Eynde, Beno?t J.,Zoete, Vincent,Michielin, Olivier
experimental part, p. 1172 - 1189 (2010/08/05)
Indoleamine 2,3-dioxygenase (IDO) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. We have used the evolutionary docking algorithm EADock to design new inhibitors of this enzyme. First, we investigated the modes of binding of all known IDO inhibitors. On the basis of the observed docked conformations, we developed a pharmacophore model, which was then used to devise new compounds to be tested for IDO inhibition.We also used a fragment-based approach to design and to optimize small organic molecule inhibitors. Both approaches yielded several new low-molecular weight inhibitor scaffolds, the most active being of nanomolar potency in an enzymatic assay. Cellular assays confirmed the potential biological relevance of four different scaffolds.
Conjugate Addition of Acylate-Nickel Complexes to Quinone Monoketals: Formal Synthesis of the Naphthoquinone Antibiotics Nanaomycin A and Deoxyfrenolicin
Semmelhack, M. F.,Keller, L.,Sato, T.,Spiess, E. J.,Wulff, W.
, p. 5566 - 5574 (2007/10/02)
A direct approach to the synthesis of isochromanone antibiotics such as nanaomycin A (2) and deoxyfrenolicin (3) is the conjugate addition of a carbonyl anion equivalent to the appropriate naphthoquinone monoketal followed by trapping with an allylic hali
