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Tumour-targetted Boranes. Part 2. Coupling of closo-Carboranes to Substituted 2-Nitroimidazoles via 1,3-Dipolar Cycloaddition

DOI: 10.1039/P19940000203

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 203 - 210 (1994)

Update date:2022-08-05

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Authors:

Scobie. MartinScobie. Martin

Mahon, Mary F.Mahon, Mary F.

Threadgill, Michael D.Threadgill, Michael D.

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Article abstract of DOI:10.1039/P19940000203

Carboranes targetted to specific tumour tissues are important for boron neutron capture therapy of cabcer.Direct syntheses of carboranes linked to 2-nitroimidazole were unsuccesful.A mild procedure for 1,3-dipolar cycloaddition of 4-(carboranylmethoxy)benzonitrile N-oxide 32 with a nitroimidazolyl-alkene 27 and with nitroimidazolyl-alkynes 3 and 30 has been developed, using a series of model reactions, yielding a dihydroisixazole 28 and the isoxazole 29 and 31, respectively.The nitrile oxide 32 is unusually stable.Dithioacetals are shown to be suitable protecting groups for aromatic aldehydes under the vigorous reductive and Lewis acidic-basic conditions of carborane formation. 6-Methoxy-4H-<1>benzopyrano<4,3-c>isoxazole 16 has been synthesised by intramolecular 1,3-dipolar cycloaddition.The structure of the isoxasole derivative 29 has been confirmed by an X-ray crystal structure analysis.

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Product name:1-(4-(3-{4-(1,2-dicarba-closo-dodecaboran(12)-1-ylmethoxy)phenyl}-4,5-dihydroisoxazol-5-yl)butyl)-2-nitroimidazole

Cas No:143334-77-4

143334-77-4

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