NNC-25-2504
Chemical Name: 3-Cyano-4-hydroxy-N'-[1-(2,3,5,6-tetramethylbenzyl)-1H-indol-4-ylmethylene]benzohydrazide
CAS No. 280134-25-0
项目整合开发状态: Preclinical
项目研究机构: Novo Nordisk (Originator), Pfizer (Originator)
合成路线:Alkylation of the sodium salt of indole-4-carbaldehyde (I) with 2,3,5,6-tetramethylbenzyl chloride (II) affords the N-alkylated indole aldehyde (III).Subsequent condensation of aldehyde (III) with 3-cyano-4-hydroxybenzoic acid hydrazide (IV) in DMSO in the presence of an acidic catalyst yields the target acyl hydrazone.
📌 参考资料/链接：
参考文献标题:Glucagon antagonists/inverse agonists
文献作者:Lau,J.; Madsen,P.; Truesdale,L.K.; Sams,C.; Feng,J.; Kiel,D.; Ling,A.; Kukl,A.; Shi,S.; Plewe,M.B.; May,J.(Agouron Pharmaceuticals,Inc.; Novo Nordisk A/S)
参考来源:JP 2002533439; WO 0039088
📄 详细内容
合成路线:Alkylation of the sodium salt of indole-4-carbaldehyde (I) with 2,3,5,6-tetramethylbenzyl chloride (II) affords the N-alkylated indole aldehyde (III).Subsequent condensation of aldehyde (III) with 3-cyano-4-hydroxybenzoic acid hydrazide (IV) in DMSO in the presence of an acidic catalyst yields the target acyl hydrazone.
参考文献标题:Optimization of alkylidene hydrazide based human glucagon receptor antagonists.Discovery of the highly potent orally available 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide
文献作者:Madsen,P.; Ling,A.; Plewe,M.; Sams,C.K.; Knudsen,L.B.; Sidelmann,U.G.; Ynddal,L.; Brand,C,L.; Andersen,B.; Murphy,D.; Teng,M.; Truesdale,L.K.; Kiel,D.; May,J.M.; Kuki,A.; Shi,S.; Johnson,M.D.; Teston,K.A.; Feng,J.; Lakis,J.; et al.
参考来源:J Med Chem 2002,45(26),5755
产品链接: CAS No. 280134-25-0››