- Cubanes in medicinal chemistry: Synthesis of functionalized building blocks
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A collection of novel, pharmaceutically relevant cubane-containing molecules has been prepared from the commercially available cubane-1,4- dimethylester. A range of synthetic methods have been applied to prepare these cubane building blocks with one or two functional handles to allow easy incorporation into existing medicinal chemistry programs.
- Wlochal, Joanna,Davies, Robert D. M.,Burton, Jonathan
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supporting information
p. 4094 - 4097
(2014/09/29)
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- Building with cubane-1,4-diyl. Synthesis of aryl-substituted cubanes, p- [n]cubyls, and cubane-separated bis(arenes)
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On treatment with an organolithium 1,4-diiodocubane generates cubane- 1,4-diyl, a highly reactive species, shown here to be a versatile precursor to numerous aryl substituted cubanes, available now for the first time in high yield. The diyl is demonstrated to provide a good route to bicubyl and its derivatives. A kind of 'living polymerization' of the diyl is developed to give the p-[n]cubyls. These oligomers are rigid rods made up to cubanes linked together at the 1 and 4 positions, each cubane adding ~4.15 ? to the length. The properties of these rods, some more than 15 ? long, are discussed; as are methods for modifying their solubility. X-ray crystallographic analyses of some of these compounds are presented, with emphasis on packing parameters.
- Eaton, Philip E.,Pramod, Kakumanu,Emrick, Todd,Gilardi, Richard
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p. 4111 - 4123
(2007/10/03)
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- 4-Substituted cubylcarbinylamines: A new class of mechanism-based monoamine oxidase B inactivators
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Cubylcarbinylamine (1a), (4-cyclopropylcubyl)carbinylamine (1b), and (4- phenylcubyl)carbinylamine (1c) were synthesized and shown to be time- dependent, irreversible inactivators of monoamine oxidase B (MAO B). Substrate protects the enzyme from inactiva
- Zhou,Li,Upadhyaya,Eaton,Silverman
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p. 1165 - 1168
(2007/10/03)
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- Homolytic reactions of cubanes, generation and characterization of cubyl and cubylcarbinyl radicals
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A series of 4-substituted cubyl radicals was generated by bromine atom abstraction from 1-bromo-4-substituted cubanes. EPR observations showed that the cubyl radicals abstracted secondary hydrogen atoms from the ethyl groups of triethylsilane and decayed
- Della, Ernest W.,Head, Nicholas J.,Mallon, Philip,Walton, John C.
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p. 10730 - 10738
(2007/10/02)
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