Application of the Stille coupling reaction to the synthesis of C2-substituted endo-exo unsaturated pyrrolo[2,1-c][1,4]benzodiazepines (PBDs)

Arnaud C. Tiberghien, David Hagan, Philip W. Howard, David E. Thurston

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

The Stille coupling reaction has been used to introduce novel vinyl, alkynyl and heterocyclic substituents to the C2-position of pyrrolo[2,1-c][1,4]benzodiazepine dilactams. Sodium borohydride reduction followed by N10-SEM deprotection has provided five analogues (6b, 8a–d) that contain C2-endo/exo-unsaturation and novel C2-substituents. These analogues have significant multilog cytotoxicity profiles in the NCI 60-Cell Line screen, and provide new SAR data for the PBD family.
Original languageEnglish
Pages (from-to)5041-5044
Number of pages4
JournalBioorganic & medicinal chemistry letters
Volume14
Issue number20
DOIs
Publication statusPublished - 18 Oct 2004

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