Synthesis of Ring- and Side-Chain-Substituted m-Iodobenzylguanidine Analogues

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• 作者：Ganesan Vaidyanathan ; Sriram Shankar ; and Michael R. Zalutsky
• 刊名：Bioconjugate Chemistry
• 出版年：2001
• 出版时间：September 2001
• 年：2001
• 卷：12
• 期：5
• 页码：786 - 797
• 全文大小：137K
• 年卷期：v.12,no.5(September 2001)
• ISSN：1520-4812

文摘

With the goal of developing MIBG analogues with improved targeting properties especially for oncologicapplications, several radioiodinated ring- and side-chain-substituted MIBG analogues were synthesized.Except for 3-[¹³¹I]iodo-4-nitrobenzylguanidine and N-hydroxy-3-[¹³¹I]iodobenzylguanidine, the radioiodinated analogues were prepared at no-carrier-added levels from their respective tin precursors.The radiochemical yields generally were in the range of 70-90% except for 3-amino-5-[¹³¹I]iodobenzylguanidine for which a radiochemical yield of about 40% was obtained. While the siliconprecursor N¹,N²-bis(tert-butyloxycarbonyl)-N¹-(4-nitro-3-trimethylsilylbenzyl)guanidine did not yield3-[¹³¹I]iodo-4-nitrobenzylguanidine, its deprotected derivative, N¹-(4-nitro-3-trimethylsilylbenzyl)guanidine was radioiodinated in a modest yield of 20% providing 3-[¹³¹I]iodo-4-nitrobenzylguanidine.Exchange radioiodination of 3-iodo-4-nitrobenzylguanidine gave 3-[¹³¹I]iodo-4-nitrobenzylguanidinein 80% radiochemical yield. No-carrier-added [¹³¹I]NHIBG was prepared from its silicon precursorN¹-hydroxy-N³-(3-trimethylsilylbenzyl)guanidine in 85% radiochemical yield.