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Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2410-5. doi: 10.1002/anie.201411493. Epub 2015 Jan 7.

Nitrosopurines en route to potently cytotoxic asmarines.

Author information

1
Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, CA 92037 (USA).

Abstract

A nitrosopurine ene reaction easily assembles the asmarine pharmacophore and transmits remote stereochemistry to the diazepine-purine hetereocycle. This reaction generates potent cytotoxins which exceed the potency of asmarine A (1.2 μM IC50) and supersede the metabolites as useful leads for biological discovery.

KEYWORDS:

alkaloids; ene reaction; natural products; structure-activity relationships; terpenoids

PMID:
25580910
PMCID:
PMC4470469
DOI:
10.1002/anie.201411493
[Indexed for MEDLINE]
Free PMC Article

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