Synthesis of a novel C-branched polyhydroxylated cyclic nitrone
- Corresponding author: Yu Chu-Yi, yucy@iccas.ac.cn
Citation:
Wu Qing-Kun, Li Yi-Xian, Jia Yue-Mei, Yu Chu-Yi. Synthesis of a novel C-branched polyhydroxylated cyclic nitrone[J]. Chinese Chemical Letters,
;2017, 28(4): 909-912.
doi:
10.1016/j.cclet.2016.12.033
Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Sugar-mimic glycosidase inhibitors:natural occurrence biological activity and prospects for therapeutic application[J]. Tetrahedron:Asymmetry, 2000,11:1645-1680. doi: 10.1016/S0957-4166(00)00113-0
Watson A.A., Fleet G.W.J., Asano N., Molyneux R.J., Nash R.J. Polyhydroxylated alkaloids-natural occurrence and therapeutic applications[J]. Phytochemistry, 2001,56:265-295. doi: 10.1016/S0031-9422(00)00451-9
Decroocq C., Stauffert F., Pamlard O.. Iminosugars as a new class of cholinesterase inhibitors[J]. Bioorg.Med.Chem.Lett., 2015,25:830-833. doi: 10.1016/j.bmcl.2014.12.071
Chen H., Hao L., Zhu M.. Synthesis of bi-/tricyclic azasugars fused thiazinan-4-one and their HIV-RT inhibitory activity[J]. Bioorg.Med.Chem.Lett., 2014,24:3426-3429. doi: 10.1016/j.bmcl.2014.05.079
Lahiri R., Ansari A.A., Vankar Y.D. Recent developments in design and synthesis of bicyclic azasugars, carbasugars and related molecules as glycosidase inhibitors[J]. Chem.Soc.Rev., 2013,42:5102-5118. doi: 10.1039/c3cs35525j
Hill C.H., Viuff A.H., Spratley S.J.. Azasugar inhibitors as pharmacological chaperones for Krabbe disease[J]. Chem.Sci., 2015,6:3075-3086. doi: 10.1039/C5SC00754B
Li Q., Ye X.S. Iminosugars as immunomodulating agents:synthesis and biological activities of 1-deoxynojirimycin and related compounds[J]. Isr.J. Chem., 2015,55:336-346. doi: 10.1002/ijch.v55.3/4
Takahata H. Synthetic medicinal chemistry of the biomolecular components mimics[J]. Yakugaku Zasshi, 2013,133:575-585. doi: 10.1248/yakushi.13-00054
Takahata H. Chiral synthesis of iminosugars[J]. Heterocycles, 2012,85:1351-1376. doi: 10.3987/REV-12-734
Concia A.L., Gomez L., Parella T., Joglar J., Clapes P. Casuarine stereoisomers from achiral substrates:chemoenzymatic synthesis and inhibitory properties[J]. J.Org.Chem., 2014,79:5386-5389. doi: 10.1021/jo500991p
Lin C.K., Cheng L.W., Li H.Y., Yun W.Y., Cheng W.C. Synthesis of novel polyhydroxylated pyrrolidine-triazole/-isoxazole hybrid molecules[J]. Org. Biomol.Chem., 2015,13:2100-2107. doi: 10.1039/C4OB01934B
Si C.M., Mao Z.Y., Dong H.Q.. Divergent method to trans-5-hydroxy-6-alkynyl/alkenyl-2-piperidinones:syntheses of (-)-epiquinamide and (+)-swainsonine[J]. J.Org.Chem., 2015,80:5824-5833. doi: 10.1021/acs.joc.5b00803
Martella D., D'Adamio G., Parmeggiani C.. Cycloadditions of sugar-derived nitrones targeting polyhydroxylated indolizidines[J]. Eur.J.Org.Chem., 2016:1588-1598.
Soluch M., Grzeszczyk B., Staszewska-Krajewska O., Chmielewski M., Furman B.. Synthesis of thienamycin methyl ester from 2-deoxy-D-ribose via Kinugasa reaction[J]. J.Antibiot., 2016,69:164-168. doi: 10.1038/ja.2015.108
Boisson J., Thomasset A., Racine E.. Hydroxymethyl-branched polyhydroxylated indolizidines:novel selective a-glucosidase inhibitors[J]. Org.Lett., 2015,17:3662-3665. doi: 10.1021/acs.orglett.5b01505
Song Y.Y., Kinami K., Kato A.. First total synthesis of(+)-broussonetine W: glycosidase inhibition of natural product&analogs[J]. Org.Biomol.Chem., 2016,14:5157-5174. doi: 10.1039/C6OB00720A
Qian B.C., Kamori A., Kinami K.. Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars[J]. Org. Biomol.Chem., 2016,14:4488-4498. doi: 10.1039/C6OB00531D
Li Y.X., Iwaki R., Kato A.. Fluorinated radicamine A and B:synthesis and glycosidase inhibition[J]. Eur.J.Org.Chem., 2016:1429-1438.
Zhu J.S., Nakagawa S., Chen W.. Synthesis of eight stereoisomers of pochonicine:nanomolar inhibition of beta-N-acetylhexosaminidases[J]. J.Org. Chem., 2013,78:10298-10309. doi: 10.1021/jo401694e
Zhang W., Sato K., Kato A.. Synthesis of fully substituted polyhydroxylated pyrrolizidines via cope-house cyclization[J]. Org.Lett, 2011,13:4414-4417. doi: 10.1021/ol201749c
Best D., Jenkinson S.F., Saville A.W.. Cystic fibrosis and diabetes:isoLAB and isoDAB enantiomeric carbon-branched pyrrolidine iminosugars[J]. Tetrahedron Lett., 2010,51:4170-4174. doi: 10.1016/j.tetlet.2010.05.131
Cruz F.P.d., Newberry S., Jenkinson S.F.. 4-C-Me-DAB and 4-C-Me-LAB— enantiomeric alkyl-branched pyrrolidine iminosugars—are specific and potent a-glucosidase inhibitors; acetone as the sole protecting group[J]. Tetrahedron Lett., 2011,52:219-223. doi: 10.1016/j.tetlet.2010.10.173
Pawar N.J., Parihar V.S., Chavan S.T.. α-Geminal dihydroxymethyl piperidine and pyrrolidine iminosugars:synthesis, conformational analysis, glycosidase inhibitory activity, and molecular docking studies[J]. J.Org.Chem., 2012,77:7873-7882. doi: 10.1021/jo3009534
Jenkinson S.F., Best D., Saville A.W.. C-branched iminosugars:alpha-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat[J]. J.Org.Chem., 2013,78:7380-7397. doi: 10.1021/jo4005487
Cren S., Wilson C., Thomas N.R. A rapid synthesis of hexofuranose-like iminosugars using ring-closing metathesis[J]. Org.Lett., 2005,7:3521-3523. doi: 10.1021/ol051232b
Li H., Zhang Y., Favre S.. Synthesis of branched seven-membered 1-N-iminosugars and their evaluation as glycosidase inhibitors[J]. Carbohydr.Res., 2012,356:110-114. doi: 10.1016/j.carres.2011.10.039
Zhang E., Bai P.Y., Sun W.. Synthesis and glycosidase inhibition evaluation of(3S, 4S)-3-((R)-1, 2-dihydroxyethyl)pyrrolidine-3, 4-diol[J]. Carbohydr.Res., 2016,434:33-36. doi: 10.1016/j.carres.2016.08.003
F.León , Brouard I., Rivera A.. Isolation, structure elucidation, total synthesis, and evaluation of new natural and synthetic ceramides on human SK-MEL-1 melanoma cells[J]. J.Med.Chem., 2006,49:5830-5839. doi: 10.1021/jm0605334
Wang W.B., Huang M.H., Li Y.X.. A practical synthesis of sugar-derived cyclic nitrones:powerful synthons for the synthesis of iminosugars[J]. Synlett, 2010:488-492.
Huiju Cao , Lei Shi . sp1-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094
Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
Yifei Zhang , Yuncong Xue , Laiwei Gao , Rui Liao , Feng Wang , Fei Wang . Merging non-covalent and covalent crosslinking: En route to single chain nanoparticles. Chinese Chemical Letters, 2024, 35(6): 109217-. doi: 10.1016/j.cclet.2023.109217
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO3−x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
Xinyu Yu , Fei Wu , Xianglang Sun , Linna Zhu , Baoyu Xia , Zhong'an Li . Low-cost dopant-free fluoranthene-based branched hole transporting materials for efficient and stable n-i-p perovskite solar cells. Chinese Chemical Letters, 2024, 35(10): 109821-. doi: 10.1016/j.cclet.2024.109821
Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp3)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647