title: Novel synthesis of 8-deaza-5,6,7,8-tetrahydroaminopterin analogues via an aziridine intermediate.
abstract: An efficient method for the construction of the tetrahydrofolate skeleton is described. Starting from pterin analogues and aromatic amines, 8-deaza-5,6,7,8-tetrahydroaminopterin derivatives and the heterocyclic benzoyl isosteres were synthesized via a novel aziridine intermediate. Following this method, the byproducts of carbon-nitrogen bond hydrogenolysis in traditional synthetic strategy can be completely avoided.
authors.affiliation: Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
authors.forename: Shouxin
authors.initials: S
authors.lastname: Zhou
authors.forename: Chao
authors.initials: C
authors.lastname: Tian
authors.forename: Chao
authors.initials: C
authors.lastname: Li
authors.forename: Ying
authors.initials: Y
authors.lastname: Guo
authors.forename: Xiaowei
authors.initials: X
authors.lastname: Wang
authors.forename: Junyi
authors.initials: J
authors.lastname: Liu
authors.forename: Zhili
authors.initials: Z
authors.lastname: Zhang
mesh_terms: D000630:Aminopterin / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D006865:Hydrogenation; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen / Q000737:chemistry; D013763:Tetrahydrofolates / Q000737:chemistry
chemical_list: D001388:Aziridines; D013763:Tetrahydrofolates; C030371:5,6,7,8-tetrahydrofolic acid; C033132:aziridine; D002244:Carbon; D000630:Aminopterin; D009584:Nitrogen