Conversion of lapachol to lomatiol: synthesis of novel naphthoquinone derivatives

Autor:	Soundararasu Senthilkumar, Kenneth O. Eyong, Kiran Chinthapally, Marc Lamshöft, Sundarababu Baskaran, Gabriel N. Folefoc
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Broad spectrum chemistry biology Yield (chemistry) Materials Chemistry Bignoniaceae General Chemistry biology.organism_classification Combinatorial chemistry Catalysis Naphthoquinone Lapachol
Zdroj:	New Journal of Chemistry. 39:9611-9616
ISSN:	1369-9261 1144-0546
DOI:	10.1039/c5nj01484k
Popis:	Lapachol (1), a naphthoquinone isolated mostly from the plants of the bignoniaceae family has a broad spectrum of biological activities and as a consequence it has been the object of different chemical transformations. Lomatiol (3), another naturally occurring naphthoquinone having structural similarities to lapachol, has been obtained from chemical and microbial transformations of lapachol in very low yields. In the present study, an easy approach for the synthesis of lomatiol (3) from lapachol (1) has been developed using SeO2 oxidation in 90% yield. Lomatiol, under epoxidation conditions afforded novel furano- and pyrano-naphthoquinone derivatives, which are analogues of anticancer agents, 2-acetylfuronaphthoquinone and β-lapachone. Most of the structures were unambiguously confirmed by single crystal X-ray analysis.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::edc2d86a3804f93829fc116c313fc869 https://doi.org/10.1039/c5nj01484k Zobrazit plný text záznamu