Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity
摘要:
2-Thia-4-azabicyclo[3.3.1]non-3-en-3-amine was synthesized as a lipophilic analogue of NO-synthase inhibitor 2-amino-5,6-dihydro-4H-1,3-thiazine and found to be a potent inhibitor of inducible NO-synthase in vitro. The crystal structure of the key intermediate 2-thia-4-azabicyclo[3.3.1]nonane-3-thione (obtained by cyclization of trans-3-bromocyclohexylamine with carbon disulfide) was determined by X-ray analysis.
[EN] TRIAZOLYL DERIVATIVES AS SYK INHIBITORS<br/>[FR] DÉRIVÉS TRIAZOLYLE EN TANT QU'INHIBITEURS DE LA SYK
申请人:MERCK SHARP & DOHME
公开号:WO2014048065A1
公开(公告)日:2014-04-03
Provided are triazole derivatives of Formula I which are potent inhibitors of spleen tyrosine kinase and pharmaceutical composition. The triazole derivatives are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD, rheumatoid arthritis, and cancer.
Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
作者:David K. Romney、Sean M. Colvin、Scott J. Miller
DOI:10.1021/ja508757g
日期:2014.10.8
We report a peptide-based catalyst that can strongly influence the regio- and enantioselectivity of the Baeyer–Villiger (BV) oxidation of cyclic ketones bearing amide, urea, or sulfonamide functional groups. Both types of selectivity are thought to arise from a catalyst–substrate hydrogen-bonding interaction. Furthermore, in selected cases, the reactions exhibit the hallmarks of parallel kinetic resolution
A comparative approach to the most sustainable protocol for the β-azidation of α,β-unsaturated ketones and acids
作者:John Andraos、Eleonora Ballerini、Luigi Vaccaro
DOI:10.1039/c4gc01282h
日期:——
In this contribution we have used green metrics analysis to compare the material efficiency, environmental impact, and safety-hazard impact in order to compare flow and batch procedures for azidation of α,β-unsaturated carbonyls.
Novel solid fluorides were prepared to optimize the β‐azidation of α,β‐unsaturated ketones. The higher loading of these catalysts compared to that of commercially available fluorides has allowed the use of a smaller mass of catalyst helping the mixing of the reaction mixture. Porous polymeric supports have proved to be more efficient in the presence of water as reaction medium. Water has played a crucial
Amine-Catalyzed Addition of Azide Ion to α,β-Unsaturated Carbonyl Compounds
作者:David J. Guerin、Thomas E. Horstmann、Scott J. Miller
DOI:10.1021/ol9909076
日期:1999.10.1
[formula: see text] A new protocol for the beta-azidation of alpha,beta-unsaturated carbonylcompounds is described. The method employs tertiary amines as catalysts for azide addition. The azide source is a 1:1 mixture of TMSN3 and AcOH. Tertiary amines, either in solution or bound to a solid support, are efficient catalysts for the reaction.