吡咯烷单环类似物及其立体异构体的合成：追求简化结构和强效β-乙酰氨基葡萄糖苷酶抑制作用。
Synthesis of Pyrrolidine Monocyclic Analogues of Pochonicine and Its Stereoisomers: Pursuit ofSimplified Structures and Potent β--Acetylhexosaminidase Inhibition.
机构信息
Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
出版信息
Molecules. 2020 Mar 25;25(7):1498. doi: 10.3390/molecules25071498.
Ten pairs of pyrrolidine analogues of pochonicine and its stereoisomers have been synthesized from four enantiomeric pairs of polyhydroxylated cyclic nitrones. Among the ten N-acetylamino pyrrolidine analogues, only compounds with 2,5-dideoxy-2,5-imino-d-mannitol (DMDP) and pochonicine (1) configurations showed potent inhibition of β-N-acetylhexosaminidases (β-HexNAcases); while 1-amino analogues lost almost all their inhibitions towards the tested enzymes. The assay results reveal the importance of the -acetylamino group and the possible right configurations of pyrrolidine ring required for this type of inhibitors.
已从四个对映体多羟基环状亚硝酮合成了 10 对吡咯烷类似物及其对映异构体。在十个 N-乙酰氨基吡咯烷类似物中，只有具有 2,5-二脱氧-2,5-亚氨基-D-甘露醇（DMDP）和 pochonicine（1）构型的化合物对β-N-乙酰氨基己糖苷酶（β-HexNAcases）表现出强烈的抑制作用；而 1-氨基类似物对测试的酶几乎失去了所有的抑制作用。该测定结果揭示了 -乙酰氨基基团的重要性，以及该类抑制剂所需的吡咯烷环的可能正确构型。
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