Synthesis of the first example of a C2-C3/C2 ‘-C3 ‘-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine dimer
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We report the first example of a C2-C3/C2’-C3’-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimer 16 synthesised through a new and efficient route, thus establishing that C2-C3-endo unsaturation enhances both cytotoxicity and DNA-binding affinity in A-Ring-linked PBD dimers but to a lesser extent than C2/C2’-exo-unsaturation. This new route has allowed the preparation of multi-gram quantities of the related clinical candidate 1 and should lead to more structurally diverse PBD dimer analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.
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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 pp. 2859 - 2862