Synthesis and enzyme inhibition study of unnatural saturated and unsaturated C-alkyl pyrrolidine iminosugars from D-mannose derived nitrone

被引:10
作者
Das, Pintu [1 ]
Kundooru, Somireddy [1 ]
Pandole, Ravikant [1 ]
Sharma, Sandeep K. [2 ]
Singh, Bhupendra N. [2 ]
Shaw, Arun K. [1 ]
机构
[1] CSIR Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226031, Uttar Pradesh, India
[2] CSIR Cent Drug Res Inst, Div Microbiol, Lucknow 226031, Uttar Pradesh, India
关键词
ALPHA-GLUCOSIDASE INHIBITORS; TYPE-2; DIABETES-MELLITUS; CYCLIC NITRONES; GLYCOSIDASE INHIBITORS; NATURAL OCCURRENCE; GENERAL-SYNTHESIS; VERSATILE ACCESS; RADICAMINE-B; CYCLOADDITION; DESIGN;
D O I
10.1016/j.tetasy.2015.12.003
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The C-alkylated biologically important pyrrolidine iminosugars have been synthesized from commercially available D-mannose. The key step of this strategy involves the diastereoselective Grignard addition to D-mannose derived nitrone 7. These unnatural iminosugars have also been tested against several glycosidases and some of them showed weak inhibition against some glucosidases. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:101 / 106
页数:6
相关论文
共 64 条
[1]   Synthesis and 1,3-dipolar cycloadditions of a new enantiopure cyclic nitrone [J].
Alibés, R ;
Blanco, P ;
de March, P ;
Figueredo, M ;
Font, J ;
Alvarez-Larena, A ;
Piniella, JF .
TETRAHEDRON LETTERS, 2003, 44 (03) :523-525
[2]   A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton [J].
Archibald, Glenn ;
Lin, Chih-Pei ;
Boyd, Peter ;
Barker, David ;
Caprio, Vittorio .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18) :7968-7980
[3]   Design, synthesis and biological evaluation of bicyclic iminosugar hybrids: conformational constraint as an effective tool for tailoring the selectivity of α-glucosidase inhibitors [J].
Arora, Inderpreet ;
Kashyap, Vivek Kr ;
Singh, Alok Kumar ;
Dasgupta, Arunava ;
Kumar, Brijesh ;
Shaw, Arun K. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (35) :6855-6868
[4]   Glycosidase inhibitors: update and perspectives on practical use [J].
Asano, N .
GLYCOBIOLOGY, 2003, 13 (10) :93R-104R
[5]   Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].
Asano, N ;
Nash, RJ ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680
[6]   Hydroxymethyl-Branched Polyhydroxylated Indolizidines: Novel Selective α-Glucosidase Inhibitors [J].
Boisson, Julien ;
Thomasset, Amelia ;
Racine, Emilie ;
Cividino, Pascale ;
Sainte-Luce, Thomas Banchelin ;
Poisson, Jean-Francois ;
Behr, Jean-Bernard ;
Py, Sandrine .
ORGANIC LETTERS, 2015, 17 (15) :3662-3665
[7]   Double addition of grignard reagents to N-glycosyl nitrones:: A new tool for the contruction of enantiopure azaheterocycles [J].
Bonanni, M ;
Marradi, M ;
Cicchi, S ;
Faggi, C ;
Goti, A .
ORGANIC LETTERS, 2005, 7 (02) :319-322
[8]  
Breuer HWM, 2003, INT J CLIN PHARM TH, V41, P421
[9]   A direct and versatile access to α,α-disubstituted 2-pyrrolidinylmethanols by Sml2-mediated reductive coupling [J].
Burchak, Olga N. ;
Philouze, Christian ;
Chavant, Pierre Yves ;
Py, Sandrine .
ORGANIC LETTERS, 2008, 10 (14) :3021-3023
[10]   Straightforward synthesis of (1→2)-linked pseudo aza-C-disaccharides by the novel cycloaddition of enantiopure cyclic nitrones to glycals [J].
Cardona, F ;
Valenza, S ;
Picasso, S ;
Goti, A ;
Brandi, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7311-7318