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通过 Ugi 反应和脱硫反应合成含二氟甲基的假肽。

Novel synthesis of pseudopeptides bearing a difluoromethyl group by Ugi reaction and desulfanylation.

机构信息

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.

出版信息

Beilstein J Org Chem. 2011;7:1070-4. doi: 10.3762/bjoc.7.123. Epub 2011 Aug 8.

DOI:10.3762/bjoc.7.123
PMID:21915210
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3170163/
Abstract

Thirteen difluoromethyl-containing pseudopeptides were synthesized by Ugi reaction using the novel building block 2,2-difluoro-2-(phenylthio)acetic acid (2) as one component, followed by removal of the phenylsulfanyl protecting group in the presence of tributyltin hydride and azobisisobutyronitrile.

摘要

十三种含二氟甲基的假肽通过 Ugi 反应合成，使用新型砌块 2,2-二氟-2-（苯硫基）乙酸（2）作为一个组分，随后在三丁基氢化锡和偶氮二异丁腈存在下除去苯硫基保护基。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d45e/3170163/9b930e3cf40e/Beilstein_J_Org_Chem-07-1070-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d45e/3170163/a44819bfa4af/Beilstein_J_Org_Chem-07-1070-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d45e/3170163/1afe97824787/Beilstein_J_Org_Chem-07-1070-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d45e/3170163/9b930e3cf40e/Beilstein_J_Org_Chem-07-1070-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d45e/3170163/a44819bfa4af/Beilstein_J_Org_Chem-07-1070-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d45e/3170163/1afe97824787/Beilstein_J_Org_Chem-07-1070-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d45e/3170163/9b930e3cf40e/Beilstein_J_Org_Chem-07-1070-g005.jpg

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本文引用的文献

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J Fluor Chem. 2010 Aug;131(8):829-843. doi: 10.1016/j.jfluchem.2010.05.014. Epub 2010 Jun 4.
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A general strategy for construction of a difluoromethyl compound library and its application in synthesis of pseudopeptides bearing a terminal difluoromethyl group.一种构建二氟甲基化合物库的通用策略及其在合成含末端二氟甲基的拟肽中的应用。
Org Biomol Chem. 2010 May 21;8(10):2386-91. doi: 10.1039/c000835d. Epub 2010 Mar 17.
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Zinc chloride promoted formal oxidative coupling of aromatic aldehydes and isocyanides to alpha-ketoamides.
氯化锌促进了芳香醛和异氰化物的形式氧化偶联反应，生成了α-酮酰胺。
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Synthesis and enzymatic evaluation of novel partially fluorinated thiol dual ACE/NEP inhibitors.新型部分氟化硫醇双效ACE/NEP抑制剂的合成与酶活性评估
Bioorg Med Chem Lett. 2009 Aug 15;19(16):4715-9. doi: 10.1016/j.bmcl.2009.06.064. Epub 2009 Jun 21.
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New fluorinated peptidomimetics through tandem aza-michael addition to alpha-trifluoromethyl acrylamide acceptors: synthesis and conformational study in solid state and solution.通过对α-三氟甲基丙烯酰胺受体进行串联氮杂迈克尔加成反应合成新型氟化拟肽：固态和溶液中的合成及构象研究
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Novel fluorinated pseudopeptides as proteasome inhibitors.新型氟化拟肽作为蛋白酶体抑制剂
Bioorg Med Chem Lett. 2009 Jan 1;19(1):83-6. doi: 10.1016/j.bmcl.2008.11.012. Epub 2008 Nov 7.
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J Am Chem Soc. 2007 Dec 19;129(50):15615-22. doi: 10.1021/ja075373f. Epub 2007 Nov 28.
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Chiral dipeptide mimics possessing a fluoroolefin moiety: a relevant tool for conformational and medicinal studies.具有氟代烯烃部分的手性二肽模拟物：构象和药物研究的相关工具。
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