Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates

被引：42
|
作者：
Kumar, Dhananjay [1 ]
Mishra, Kunj B. [1 ]
Mishra, Bhuwan B. [1 ]
Mondal, Saheli [1 ]
Tiwari, Vinod K. [1 ]
机构：
[1] Banaras Hindu Univ, Fac Sci, Ctr Adv Study, Dept Chem, Varanasi 221005, Uttar Pradesh, India
来源：
STEROIDS | 2014年 / 80卷
关键词：
Click chemistry; Ethisterone; Carbohydrate; Glycoconjugate; FUTURE DRUG DISCOVERY; 1,3-DIPOLAR CYCLOADDITIONS; CARBOHYDRATE-CHEMISTRY; EXPEDIENT SYNTHESIS; GLYCOSYL; ALKYNES; MIMICS; AZIDES; PEPTIDOTRIAZOLES; SPECIFICITY;
D O I：
10.1016/j.steroids.2013.11.022
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Numerous deoxy-azido sugars 3 were prepared by the reaction of tosyl/bromo sugars with NaN3 in dry DMF under heating condition. The 1,3-dipolar cycloaddition of deoxy-azido sugars 3 with ethisterone 4 to afford regioselective triazole-linked ethisterone glycoconjugates 5 was investigated in the presence of CuI and DIPEA in dichloromethane or CuSO4 center dot 5H(2)O and sodium ascorbate in aqueous medium. All the developed compounds were characterized by spectroscopic analysis (IR, H-1 & C-13 NMR, and MS spectra). Structure of triazolyl ethisterone glycoconjugate 5a has been further confirmed by its Single Crystal X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：71 / 79
页数：9
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