Quantitative and regiocontrolled cross-photocycloaddition of the anticancer drug 5-fluorouracil achieved in a cocrystal

Andrew J E Duncan; Roxanne L Dudovitz; Shawna J Dudovitz; Jelena Stojaković; S V Santhana Mariappan; Leonard R MacGillivray

doi:10.1039/c6cc06570h

Quantitative and regiocontrolled cross-photocycloaddition of the anticancer drug 5-fluorouracil achieved in a cocrystal

Chem Commun (Camb). 2016 Nov 18;52(89):13109-13111. doi: 10.1039/c6cc06570h. Epub 2016 Oct 19.

Authors

Andrew J E Duncan¹, Roxanne L Dudovitz, Shawna J Dudovitz, Jelena Stojaković, S V Santhana Mariappan, Leonard R MacGillivray

Affiliation

¹ Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA. len-macgillivray@uiowa.edu.

PMID: 27759136
DOI: 10.1039/c6cc06570h

Abstract

We describe a [2+2] cross-photocycloaddition of the anticancer drug 5-fluorouracil in the solid state that proceeds regioselectively and in quantitative yield. The photocycloaddition occurs in a cocrystal with trans-2,2'-bis(pyridyl)ethylene.

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry*
Crystallization
Cycloaddition Reaction
Fluorouracil / chemical synthesis*
Fluorouracil / chemistry*
Models, Molecular
Molecular Conformation
Photochemical Processes*
Stereoisomerism

Substances

Antineoplastic Agents
Fluorouracil