Diversity-Oriented Synthesis and Biological Evaluation of Iminosugars from Unprotected 2-Deoxy-d-ribose

被引：10
|
作者：
Malinowski, Maciej [1 ]
Rowicki, Tomasz [1 ]
Guzik, Patrycja [1 ]
Wielechowska, Monika [1 ]
Sobiepanek, Anna [1 ]
Sas, Wojciech [1 ]
机构：
[1] Warsaw Univ Technol, Fac Chem, Ul Noakowskiego 3, PL-00664 Warsaw, Poland
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 21期
关键词：
Iminosugars; Nitrones; Carbohydrates; Cycloaddition; Biological activity; Nitrogen heterocycles; AQUEOUS-MEDIA; C-GLYCOSIDES; PHARMACOLOGICAL CHAPERONES; GALACTOSIDASE INHIBITORS; CHEMICAL-SYNTHESIS; CONVENIENT ROUTE; CHAIN ELONGATION; SUGARS; DERIVATIVES; METAL;
D O I：
10.1002/ejoc.201600459
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An exceptionally short synthesis of novel indolizidine-, quinolizidine-, and piperidine-based iminosugars from unprotected 2-deoxy-d-ribose by intramolecular 1,3-dipolar cycloaddition of sugar-derived N-(3-alkenyl)nitrones has been accomplished. The use of the 2-deoxy carbohydrate also enabled us to confirm the previously proposed mechanism for the alteration of the stereochemical course of the intramolecular 1,3-dipolar cycloaddition observed for an unprotected sugar-derived nitrone. Biological assays of the six new iminosugars revealed a slight inhibition activity of the indolizidine derivative 7a, whereas, interestingly, the two quinolizidine iminosugars 5a and 5b appeared to be weak glycosidase activators.
引用
收藏
页码：3642 / 3649
页数：8
相关论文
共 50 条
  • [21] CaCl2 as a bifunctional reusable catalyst: diversity-oriented synthesis of 4H-pyran library under ultrasonic irradiation
    Safaei, Hamid Reza
    Shekouhy, Mohsen
    Shirinfeshan, Athar
    Rahmanpur, Sudabeh
    MOLECULAR DIVERSITY, 2012, 16 (04) : 669 - 683
  • [22] DIVERSITY-ORIENTED SYNTHESIS OF 2-SUBSTITUTED PURINE NUCLEOSIDES FROM AVAILABLE NUCLEOSIDES VIA THE LATE-STAGE NITRATION/DERIVATIZATION
    Xia, Ran
    Liu, Li-Jie
    Xia, Chao
    Sun, Li -Ping
    Chen, Lei -Shan
    HETEROCYCLES, 2022, 104 (08) : 1447 - 1460
  • [23] Design and diversity-oriented synthesis of novel 1,4-thiazepan-3-ones fused with bioactive heterocyclic skeletons and evaluation of their antioxidant and cytotoxic activities
    Shi, Feng
    Zeng, Xiao-Ning
    Cao, Xu-Dong
    Zhang, Shu
    Jiang, Bo
    Zheng, Wei-Fa
    Tu, Shu-Jiang
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (01) : 743 - 746
  • [24] Diversity-Oriented Synthetic Endeavors of Newly Designed Ferrier and Ferrier-Nicholas Systems Derived from 1-C-Alkynyl-2-deoxy-2-C-Methylene Pyranosides
    Miranda, Silvia
    Gomez, Ana M.
    Cristobal Lopez, J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (39) : 5355 - 5374
  • [25] 2-[BIS(METHYLTHIO)METHYLENE]MALONONITRILE: A VERSATILE REAGENT IN THE DIVERSITY-ORIENTED SYNTHESIS OF COMPLEX HETEROCYCLIC SCAFFOLDS
    Sontakke, Sandeep
    Ubale, Prashant
    Kadam, Digambar
    Halikar, Nilesh
    Khansole, Gopinath
    Vartale, Sambhaji
    HETEROCYCLIC LETTERS, 2024, 14 (02): : 479 - 492
  • [26] A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp2)-H hydroxylation strategy
    Sun, Yong-Hui
    Sun, Tian-Yu
    Wu, Yun-Dong
    Zhang, Xinhao
    Rao, Yu
    CHEMICAL SCIENCE, 2016, 7 (03) : 2229 - 2238
  • [27] A Chiron Approach to Diversity-Oriented Synthesis of Aminocyclitols, (-)-Conduramine F-4 and Polyhydroxyaminoazepanes from a Common Precursor
    Harit, Vimal Kant
    Ramesh, Namakkal G.
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23) : 11574 - 11586
  • [28] Design, synthesis and biological evaluation of betulin-3-yl 2-amino-2-deoxy-β-D-glycopyranosides
    Myszka, Henryk
    Grzywacz, Dania
    Zdrowowicz, Magdalena
    Spisz, Paulina
    Butowska, Kamila
    Rak, Janusz
    Piosik, Jacek
    Jaskiewicz, Maciej
    Kamysz, Wojciech
    Liberek, Beata
    BIOORGANIC CHEMISTRY, 2020, 96
  • [29] Synthesis and biological evaluation of phosphoramidate prodrugs of two analogues of 2-deoxy-D-ribose-1-phosphate directed to the discovery of two carbasugars as new potential anti-HIV leads
    Hamon, Nadege
    Slusarczyk, Magdalena
    Serpi, Michaela
    Balzarini, Jan
    McGuigan, Christopher
    BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (04) : 829 - 838
  • [30] Direct One-Pot Synthesis of Nucleosides from Unprotected or 5-O-Monoprotected D-Ribose
    Downey, A. Michael
    Richter, Celin
    Pohl, Radek
    Mahrwald, Rainer
    Hocek, Michal
    ORGANIC LETTERS, 2015, 17 (18) : 4604 - 4607
12345