Synthesis of Closo-1,7-Carboranyl Alkyl Amines |
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Authors: | Agarwal Hitesh K Buszek Benjamin Ricks Kevin G Tjarks Werner |
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Affiliation: | Division of Medicinal Chemistry & Pharmacognosy, The Ohio State University, 500 West 12th Avenue, Columbus, OH 43210, USA |
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Abstract: | Of the three closo-carborane isomers (C2B10H12), 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). |
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Keywords: | m-Closo-carborane Closo-1,7-carborane Carboranyl amine |
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