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Synfacts 2020; 16(03): 0341
DOI: 10.1055/s-0039-1691716
Chemistry in Medicine and Biology
© Georg Thieme Verlag Stuttgart · New York

A Repurposed Chemotherapy Drug as C1 Synthon

Contributor(s):
Dirk Trauner
,
Belinda E. Hetzler
Svec RL, Hergenrother PJ. * University of Illinois at Urbana-Champaign, USA
Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations.

Angew. Chem. Int. Ed. 2020;
59: 1857-1862
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Further Information

Publication History

Publication Date:
18 February 2020 (online)

 
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Key words

methylation - temozolomide - diazomethane surrogates

Significance

The reagent diazomethane is employed in the formation of methyl esters, as well as for cyclopropanation reactions; however, it poses a severe risk of explosion and inhalation toxicity. In the search for alternative reagents, the authors identify the cancer chemotherapy drug temozolomide (TMZ), which is designed to methylate DNA in cancer cells.


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Comment

TMZ is a weighable solid, non-explosive and not acutely toxic. Upon hydrolysis and release of methyl diazonium, TMZ methylates a broad range of carboxylic acids. Notably, the protecting groups THP and MOM are stable to the reaction conditions. Furthermore, catalysis with Fe(TPP)Cl enables the cyclopropanation of several styrenes.


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