Nitrosopurines en route to potently cytotoxic asmarines

Kanny K. Wan; Kotaro Iwasaki; Jeffrey C. Umotoy; Dennis W. Wolan; Ryan A. Shenvi

doi:10.1002/anie.201411493

Nitrosopurines en route to potently cytotoxic asmarines

Kanny K. Wan, Kotaro Iwasaki, Jeffrey C. Umotoy, Dennis W. Wolan, Ryan A. Shenvi

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2410-2415
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	8
DOIs	https://doi.org/10.1002/anie.201411493
Publication status	Published - 2015 Feb 16
Externally published	Yes

Keywords

Alkaloids
Ene reaction
Natural products
Structure-activity relationships
Terpenoids

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201411493

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title = "Nitrosopurines en route to potently cytotoxic asmarines",

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.",

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author = "Wan, {Kanny K.} and Kotaro Iwasaki and Umotoy, {Jeffrey C.} and Wolan, {Dennis W.} and Shenvi, {Ryan A.}",

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AU - Wan, Kanny K.

AU - Iwasaki, Kotaro

AU - Umotoy, Jeffrey C.

AU - Wolan, Dennis W.

AU - Shenvi, Ryan A.

PY - 2015/2/16

Y1 - 2015/2/16

N2 - 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.

AB - 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.

KW - Alkaloids

KW - Ene reaction

KW - Natural products

KW - Structure-activity relationships

KW - Terpenoids

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JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 8

ER -

Nitrosopurines en route to potently cytotoxic asmarines

Abstract

Keywords

ASJC Scopus subject areas

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