Development of carborane synthons: synthesis and chemistry of (aminoalkyl)carboranes

Autor:	Fazlul Alam, Albert H. Soloway, A. K. M. Anisuzzaman, J. Gerald Wilson
Rok vydání:	1992
Předmět:	Inorganic Chemistry Acylation Sodium borohydride chemistry.chemical_compound chemistry Hydrochloride Decaborane Functional group Synthon Carborane Moiety Physical and Theoretical Chemistry Medicinal chemistry
Zdroj:	Inorganic Chemistry. 31:1955-1958
ISSN:	1520-510X 0020-1669
Popis:	A number of (aminoalkyl)-1,2-closo-dodecaboranes have been synthesized to provide carboranes with a functional group for covalent incorporation into structures of potential use in the treatment of cancer by boron neutron capture therapy (BNCT). (Phthalimidoalkyl)acetylenes reacted with decaborane to give the corresponding carboranes; removal of the phthalimido group under mild conditions using sodium borohydride in 2-propanol furnished the (aminoalkyl)carboranes which were isolated as their hydrochloride salts. An alternative approach involved the conversion of an (iodoalkyl)- or a ((tosyloxy)alkyl)carborane to the azido derivative which gave the amine on hydrogenation. An effective way of attaching a carborane moiety to thiouracil, which is selectively taken up in melanoma cells, is illustrated by the acylation of two of these amines with thiouracil-5-carboxylic acid.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::20bf1d577c584171c058f657e781a931 https://doi.org/10.1021/ic00036a043 Zobrazit plný text záznamu