Synthesis of 7-substituted benzolactam-V8s and their selectivity for protein kinase C isozymes.
[reaction: see text] Condensation of L-valine benzyl ester toluenesulfonic acid salt with a substituted cyclohexadione followed by aromatization with the assistance of NBS provides an N-aryl L-valine benzyl ester. This intermediate is converted into 7-substituted benzolactam-V8s using an asymmetric Strecker reaction as the key step. The target molecules show a different pattern of isozyme selectivity relative to the 8-substituted benzolactam-V8s.
Ma
Dawei
D
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Lu, Shanghai 200032, China. madw@pub.sioc.ac.cn
Tang
Guozhi
G
Kozikowski
Alan P
AP
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D007700:Kinetics; D007769:Lactams / Q000138:chemical synthesis* / Q000494:pharmacology; D010084:Oxidation-Reduction; D015240:Phorbol 12,13-Dibutyrate / Q000378:metabolism; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D013379:Substrate Specificity
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D007527:Isoenzymes; D007769:Lactams; D015240:Phorbol 12,13-Dibutyrate; D011493:Protein Kinase C