title: Copper(I) mediated facile synthesis of potent tubulin polymerization inhibitor, 9-amino-α-noscapine from natural α-noscapine.
abstract: Facile synthesis of natural α-noscapine analogue, 9-amino-α-noscapine, a potent inhibitor of tubulin polymerization for cancer therapy, is achieved via copper(I) iodide mediated in situ aromatic azidation and reduction of 9-bromo-α-noscapine (obtained by bromination of natural α-noscapine) with NaN(3) in DMSO at 130°C in the presence of L-proline as an amino acid promoter. The protocol developed here avoided isolation of 9-azido-α-noscapine and did not cleave the sensitive C-C bond between two heterocyclic phthalide and isoquinoline units.
authors.affiliation: Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad 500007, India.
authors.forename: Naresh K
authors.initials: NK
authors.lastname: Manchukonda
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Sridhar
authors.forename: Pradeep K
authors.initials: PK
authors.lastname: Naik
authors.forename: Harish C
authors.initials: HC
authors.lastname: Joshi
authors.forename: Srinivas
authors.initials: S
authors.lastname: Kantevari
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008958:Models, Molecular; D009665:Noscapine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D050257:Tubulin Modulators / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C561203:9-amino-alpha-noscapine; D050257:Tubulin Modulators; D003300:Copper; D009665:Noscapine