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ChemInform Abstract: Synthesis of Sequence-Selective C8-Linked Pyrrolo(2,1-c)(1,4) benzodiazepine DNA Interstrand Cross-Linking Agents.

✍ Scribed by D. E. THURSTON; D. S. BOSE; A. S. THOMPSON; P. W. HOWARD; A. LEONI; S. J. CROKER; T. C. JENKINS; S. NEIDLE; J. A. HARTLEY; L. H. HURLEY

Publisher: John Wiley and Sons
Year: 2010
Weight: 38 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199715167

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✦ Synopsis

Synthesis of Sequence-Selective C8-Linked Pyrrolo(2,1-c)(1,4) benzodiazepine DNA Interstrand Cross-Linking Agents.

-In order to construct the key A-ring fragments (VI), a versatile convergent approach is developed to join two units of vanillic acid (I) with α,ω-dihaloalkanes (II). The "amino-thioacetal" cyclization procedure is used to produce the electrophilic DNA-interactive imine moiety during the final synthetic step ((VIII) . fwdarw. (IX)). The agents of type (IX) possess exquisite DNA cross-linking and cytotoxic properties. -(THURSTON, D.

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