184041-08-5Relevant academic research and scientific papers
Electrochemical Formation of 3,5-Diimido-1,2-dithiolanes by Dehydrogenative Coupling
Breising, Valentina M.,Gieshoff, Tile,Kehl, Anton,Kilian, Vincent,Schollmeyer, Dieter,Waldvogel, Siegfried R.
, p. 6785 - 6788 (2018/10/25)
A synthetic approach to the cyclic disulfide moiety of 3,5-diimido-1,2-dithiolane derivatives starting with readily available precursors including the electrochemical coupling of dithioanilides is developed. The electrochemical key step provides sustainab
Insights into the Mechanism of Anodic N-N Bond Formation by Dehydrogenative Coupling
Gieshoff, Tile,Kehl, Anton,Schollmeyer, Dieter,Moeller, Kevin D.,Waldvogel, Siegfried R.
, p. 12317 - 12324 (2017/09/12)
The electrochemical synthesis of pyrazolidine-3,5-diones and benzoxazoles by N-N bond formation and C,O linkage, respectively, represents an easy access to medicinally relevant structures. Electrochemistry as a key technology ensures a safe and sustainabl
Azetidine-2,4-diones (4-oxo-β-lactams) as scaffolds for designing elastase inhibitors
Mulchande, Jalmira,Guedes, Rita C.,Tsang, Wing-Yin,Page, Michael I.,Moreira, Rui,Iley, Jim
, p. 1783 - 1790 (2008/09/21)
A new class of inhibitors 4-oxo-β-lactams (azetidine-2,4-diones), containing the required structural elements for molecular recognition, inhibit porcine pancreatic elastase (PPE) but show a dramatically lower reactivity toward hydroxide compared with the analogous inhibitors 3-oxo-β-sultams. Inhibition is the result of acylation of the active site serine and electron-withdrawing substituents at the N-(4-aryl) position in 3,3-diethyl-N-aryl derivatives increasing the rate of enzyme acylation and generating a Hammett ρ-value of 0.65. Compared with a ρ-value of 0.96 for the rates of alkaline hydrolysis of the same series, this is indicative of an earlier transition state for the enzyme-catalyzed reaction. Docking studies indicate favorable noncovalent interactions of the inhibitor with the enzyme. Compound 2i, the most potent inhibitor against PPE, emerged as a very potent HLE inhibitor, with a second-order rate for enzyme inactivation of ～5 × 105 M-1 s-1.
Design and synthesis of thrombin inhibitors: Analogues of MD-805 with reduced stereogenicity and improved potency
Brundish, Derek,Bull, Alice,Donovan, Vera,Fullerton, Joseph D.,Garman, Sheila M.,Hayler, Judy F.,Janus, Diana,Kane, Peter D.,McDonnell, Mark,Smith, Garrick P.,Wakeford, Robert,Walker, Clive V.,Howarth, Graham,Hoyle, William,Allen, Mark C.,Ambler, John,Butler, Keith,Talbot, Mark D.
, p. 4584 - 4603 (2007/10/03)
Mitsubishi's MD-805, a potent and selective inhibitor of thrombin which contains four stereogenic centers, has been the starting point for an optimization program. A systematic synthetic study resulted in thrombin inhibitors achiral at P2 and P3 but with
