Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Beilstein J Org Chem. 2011;7:1745-52. doi: 10.3762/bjoc.7.205. Epub 2011 Dec 30.
A variety of 2-amino-3-arylpropan-1-ols, anti-2-amino-3-aryl-3-methoxypropan-1-ols and anti-2-amino-1-arylpropan-1,3-diols were prepared selectively through elaboration of trans-4-aryl-3-chloro-β-lactams. In addition, a number of 2-(azidomethyl)aziridines was converted into novel 2-[(1,2,3-triazol-1-yl)methyl]aziridines by Cu(I)-catalyzed azide-alkyne cycloaddition, followed by microwave-assisted, regioselective ring opening by dialkylamine towards 1-(2,3-diaminopropyl)-1,2,3-triazoles. Although most of these compounds exhibited weak antiplasmodial activity, six representatives showed moderate antiplasmodial activity against both a chloroquine-sensitive and a chloroquine-resistant strain of Plasmodium falciparum with IC(50)-values of ≤25 μM.
通过对反式-4-芳基-3-氯-β-内酰胺的精细修饰，我们选择性地制备了多种 2-氨基-3-芳基-1-丙醇、抗-2-氨基-3-芳基-3-甲氧基-1-丙醇和抗-2-氨基-1-芳基-1,3-丙二醇。此外，一些 2-(叠氮甲基)氮丙啶通过 Cu(I)-催化的叠氮-炔环加成反应转化为新型 2-[(1,2,3-三唑-1-基)甲基]氮丙啶，然后通过微波辅助、二烷基胺进行区域选择性开环反应，得到 1-(2,3-二氨基丙基)-1,2,3-三唑。尽管这些化合物大多数表现出较弱的抗疟原虫活性，但有 6 种代表性化合物对氯喹敏感和氯喹耐药的恶性疟原虫均表现出中等的抗疟原虫活性，IC50 值均≤25 μM。
