A novel approach to the synthesis of cytotoxic C2–C3 unsaturated pyrrolo[2,1-c]benzodiazepines (PBDs) with conjugated acrylyl C2-substituents

Bioorganic & Medicinal Chemistry Letters
2004.0

Abstract

A concise synthesis of three novel C2-C3 unsaturated pyrrolo[2,1-c][1,4]benzodiazepine analogues (18-20) containing conjugated acrylyl C2-substituents is reported that utilises Heck coupling to install the C2-acrylyl side chains. These analogues possess significant cytotoxicity according to the NCI 60-cell line screen with 18 surpassing anthramycin (1) in potency.

Knowledge Graph

Similar Paper

A novel approach to the synthesis of cytotoxic C2–C3 unsaturated pyrrolo[2,1-c]benzodiazepines (PBDs) with conjugated acrylyl C2-substituents
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and Antitumor Activity of a New Class of Pyrazolo[4,3-e]pyrrolo[1,2-a][1,4]diazepinone Analogs of Pyrrolo[1,4][2,1-c]benzodiazepines
Journal of Medicinal Chemistry 1994.0
Synthesis of a novel C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione library: Effect of C2-aryl substitution on cytotoxicity and non-covalent DNA binding
Bioorganic & Medicinal Chemistry 2007.0
Pyrrolo[2,1-c][1,4]benzodiazepine–anthraquinone conjugates. Synthesis, DNA binding and cytotoxicity
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and biological evaluation of anilino substituted pyrimidine linked pyrrolobenzodiazepines as potential anticancer agents
Bioorganic & Medicinal Chemistry Letters 2010.0
Synthesis and Cytotoxicity on Sensitive and Doxorubicin-Resistant Cell Lines of New Pyrrolo[2,1-c][1,4]benzodiazepines Related to Anthramycin
Journal of Medicinal Chemistry 2001.0
Structure−Activity Relationships of Monomeric C2-Aryl Pyrrolo[2,1-c][1,4]benzodiazepine (PBD) Antitumor Agents
Journal of Medicinal Chemistry 2010.0
Synthesis and anticancer activity of chalcone-pyrrolobenzodiazepine conjugates linked via 1,2,3-triazole ring side-armed with alkane spacers
European Journal of Medicinal Chemistry 2011.0
Synthesis, DNA binding, and cytotoxicity studies of pyrrolo[2,1-c][1,4]benzodiazepine-anthraquinone conjugates
Bioorganic & Medicinal Chemistry 2007.0
Phosphonate-linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: Synthesis, DNA-binding affinity and cytotoxicity
Bioorganic & Medicinal Chemistry 2008.0