CAS: 99076-56-9; (2S)-2-((Benzylsulfonyl)Amino)Propanoic Acid

相似化合物

688789-94-8 6966-44-5 1094750-93-2

上下游产品

CAS号302-72-7 DL-2-氨基丙酸

L-丙氨酸,苄磺酰氯置于potassium Carbonate体系中,化学反应 0.5H,以81%的收率获得产物n-[(苄基)磺酰基]-L-丙氨酸
参考文献:Structure-Based Design And Synthesis Of Potent Matrix Metalloproteinase Inhibitors Derived From A 6H-1,3,4-Thiadiazine Scaffold
标题:Structure-Based Design And Synthesis Of Potent Matrix Metalloproteinase Inhibitors Derived From A 6H-1,3,4-Thiadiazine Scaffold
摘要:We Describe A New Generation Of Heterocyclic Nonpeptide Matrix Metalloproteinase (Mmp) Inhibitors Derived From A 6H-1,3,4-Thiadiazine Scaffold. A Screening Effort Was Utilized To Identify Some Chiral 6-Methyl-1,3,4-Thiadiazines That Are Weak Inhibitors Of The Catalytic Domain Of Human Neutrophil Collagenase (Cdmmp-8). Further Optimization Of The Lead Compounds Revealed General Design Principles That Involve The Placement Of A Phenyl Or Thienyl Group At Position 5 Of The Thiadiazine Ring,To Improve Unprimed Side Affinity; The Incorporation Of An Amino Group At Position 2 Of The Thiadiazine Ring As The Chelating Agent For The Catalytic Zinc; The Placement Of A N-Sulfonamide-Substituted Amino Acid Residue At The Amino Group,To Improve Primed Side Affinity; And The Attachment Of Diverse Functional Groups At Position 4 Or 5 Of The Phenyl Or Thienyl Group At The Unprimed Side,To Improve Selectivity. The New Compounds Were Assayed Against Eight Different Matrix Metalloproteinases,Mmp-1,Cdmmp-2,Cdmmp-8,Mmp-9,Cdmmp-12,Cdmmp-13,Cdmmp-14,And The Ectodomain Of Mmp-14,Respectively. A Unique Combination Of The Above-Described Modifications Produced The Selective Inhibitor (2R)-N-[5-(4-Bromophenyl)-6H-1,3,4-Thiadiazin-2-Yl]-2-[(Phenylsulfonyl)Amino]Propanamide With High Affinity For Mmp-9 (K-I = 40 Nm). X-Ray Crystallographic Data Obtained For Cdmmp-8 Cocrystallized With N-Allyl-5-(4-Chlorophenyl)-6H-1,3,4-Thiadiazin-2-Amine Hydrobromide Gave Detailed Design Information On Binding Interactions For Thiadiazine-Based Mmp Inhibitors.
DOI:10.1021/jm010887P