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

Journal Article · Wed May 13 00:00:00 EDT 1992 · Inorganic Chemistry; (United States)

DOI:https://doi.org/10.1021/ic00036a043· OSTI ID:6975674

Wilson, J G ^[1]; Anisuzzaman, A K.M.; Soloway, A H ^[2]; Alam, F

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1. Australian Nuclear Science and Technology Organization, Menai, New South Wales (Australia)
2. Ohio State Univ., Columbus (United States)

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.

• DOE Contract Number: FG02-90ER60972
• OSTI ID: 6975674
• Journal Information: Inorganic Chemistry; (United States), Journal Name: Inorganic Chemistry; (United States) Vol. 31:10; ISSN 0020-1669; ISSN INOCAJ
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
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62 RADIOLOGY AND NUCLEAR MEDICINE
ACYLATION
ALCOHOLS
AMINES
BORON
BORON COMPOUNDS
CARBON COMPOUNDS
CARBORANES
CARBOXYLIC ACIDS
CHEMICAL ANALYSIS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DISEASES
ELEMENTS
HYDROXY COMPOUNDS
INFRARED SPECTRA
KINETICS
MASS SPECTRA
MEDICINE
NEOPLASMS
NEUTRON CAPTURE THERAPY
NEUTRON THERAPY
NMR SPECTRA
NUCLEAR MEDICINE
ORGANIC ACIDS
ORGANIC BORON COMPOUNDS
ORGANIC COMPOUNDS
PROPANOLS
QUALITATIVE CHEMICAL ANALYSIS
RADIOLOGY
RADIOTHERAPY
REACTION KINETICS
SEMIMETALS
SEPARATION PROCESSES
SPECTRA
THERAPY
THIN-LAYER CHROMATOGRAPHY