7065-23-8Relevant academic research and scientific papers
Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors
Platte, Simon,Korff, Marvin,Imberg, Lukas,Balicioglu, Ilker,Erbacher, Catharina,Will, Jonas M.,Daniliuc, Constantin G.,Karst, Uwe,Kalinin, Dmitrii V.
supporting information, p. 3672 - 3690 (2021/08/07)
Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.
First catalytic asymmetric hydrogenation of quinoxaline-2-carboxylates
Maj, Anna M.,Heyte, Svetlana,Araque, Marcia,Dumeignil, Franck,Paul, Sébastien,Suisse, Isabelle,Agbossou-Niedercorn, Francine
, p. 1375 - 1380 (2017/02/15)
For the first time, the asymmetric hydrogenation of quinoxaline-2-carboxylates was performed successfully. The best catalysts are based on iridium complexes modified by chiral phosphorous ligands. Accelerated examination of ligands and catalysts has been undertaken by using a Chemspeed workstation, which enables carrying out, in parallel, eight independent catalytic reactions at the laboratory scale. Tetrahydroquinoxaline-2-carboxylates could be obtained with high yields and up to 74% ee.
Sodium cyanoborohydride-mediated direct conversion of some heterocyclic aldehydes to esters
Goswami, Shyamaprosad,Hazra, Anita,Goh, Jia Hao,Fun, Hoong-Kun
experimental part, p. 2505 - 2510 (2011/09/20)
An exceptional oxidizing behavior of sodium cyanoborohydride is observed where electron-withdrawing heterocyclic aldehydes are directly converted to their corresponding esters on treatment of sodium cyanoborohydride in methanol. The spectral analysis and
One-step direct conversion of heterocyelie aldehydes to esters
Goswami, Shyamaprosad,Hazra, Anita
supporting information; experimental part, p. 484 - 485 (2010/03/04)
One-step direct conversion of a series of heteroeyelie aldehydes to heterocyclie esters is reported here by the use of thiamine hydrochloride as a catalyst in the absence of nitrogen atmosphere in a reasonably high yield. This method exclusively produces
Oxidation of diazo compounds by dimethyl dioxirane: An extremely mild and efficient method for the preparation of labile α-oxo-aldehydes
Ihmels,Maggini,Prato,Scorrano
, p. 6215 - 6218 (2007/10/02)
A novel method for the preparation of α-oxo-aldehydes by dimethyl dioxirane oxidation of α-diazoketones is described. The procedure is particularly useful when the desired compound cannot be purified by chromatography or distillation: the by-products (ace
REACTION OF β-AMINO-α,β-UNSATURATED ESTERS AND AMIDES WITH ARYL DIAZONIUM SALTS. SYNTHESIS OF CINNOLINE DERIVATIVES
Kanner, C. B.,Pandit, U. K.
, p. 3513 - 3518 (2007/10/02)
Conjugated esters and amides react with aryldiazonium salts at room temperature (MeCN) to form the corresponding iminium hydrazone derivatives, which can be thermally cyclized to cinnoline-3-esters and cinnoline-3-amides.In general the intermediate iminiu
