Journal
TETRAHEDRON LETTERS
Volume 52, Issue 43, Pages 5664-5667Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.08.101
Keywords
m-Closo-carborane; Closo-1,7-carborane; Carboranyl amine
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Funding
- Ohio State University College of Pharmacy
- NIH [R01 CA127935]
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Of the three closo-carborane isomers (C(2)B(10)H(12)), closo-1,2-carborane has been used most widely in the synthesis of carboranyl amines. However, closo-1,2-carboranes are prone to deboronation to nido-7,8-carborane under various conditions including attack by basic amino groups. In order to overcome this problem, closo-1,7-carboranyl ethyl-, propyl-, and butylamine were synthesized, which should be more stable towards basic deboronation than their closo-1,2-carboranyl counterparts. These closo-1,7-carboranyl amines (5,18 and 19) were synthesized using two different methods, both starting from the corresponding closo-1,7-carboranyl alkyl iodides (3,14 and 15). One of the carboranyl alkyl amine (5) was conjugated with folic acid to form a closo-1,7-carborane-folic acid bioconjugate (20). (C) 2011 Elsevier Ltd. All rights reserved.
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