Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates

被引：41
|
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
相关论文
共 50 条
  • [31] Facile preparation and properties of multifunctional polyacetylene via highly efficient click chemistry
    Zhang, Fayin
    Guang, Shanyi
    Ke, Fuyou
    Li, Jing
    Xu, Hongyao
    RSC ADVANCES, 2016, 6 (01) : 448 - 455
  • [32] Click chemistry inspired synthesis of ferrocene amino acids and other derivatives
    Sudhir, V. Sai
    Kumar, N. Y. Phani
    Chandrasekaran, S.
    TETRAHEDRON, 2010, 66 (06) : 1327 - 1334
  • [33] Facile synthesis of dendritic-linear-dendritic materials by click chemistry
    Jae Wook Lee
    Seung Choul Han
    Byoung-Ki Kim
    Un Yup Lee
    Sae Reum Sung
    Hwa-Shin Kang
    Ji Hyeon Kim
    Sung-Ho Jin
    Macromolecular Research, 2009, 17 : 499 - 505
  • [34] Facile Synthesis of Dendritic-Linear-Dendritic Materials by Click Chemistry
    Lee, Jae Wook
    Han, Seung Choul
    Kim, Byoung-Ki
    Lee, Un Yup
    Sung, Sae Reum
    Kang, Hwa-Shin
    Kim, Ji Hyeon
    Jin, Sung-Ho
    MACROMOLECULAR RESEARCH, 2009, 17 (07) : 499 - 505
  • [35] Facile design of biomaterials by click' chemistry
    Hvilsted, Soren
    POLYMER INTERNATIONAL, 2012, 61 (04) : 485 - 494
  • [36] Click inspired synthesis of piperazine-triazolyl sugar-conjugates as potent anti-Hela activity
    Bose, Priyanka
    Agrahari, Anand K.
    Singh, Rajan
    Singh, Mala
    Kumar, Sunil
    Singh, Rakesh K.
    Tiwari, Vinod K.
    CARBOHYDRATE RESEARCH, 2023, 529
  • [37] 'Click chemistry' in CuI-zeolites:: a convenient access to glycoconjugates
    Alix, Aurlien
    Chassaing, Stefan
    Pale, Patrick
    Sommer, Jean
    TETRAHEDRON, 2008, 64 (37) : 8922 - 8929
  • [38] Highly efficient synthesis of polyfluorinated dendrons suitable for click chemistry
    Koelmel, Dominik K.
    Nieger, Martin
    Braese, Stefan
    RSC ADVANCES, 2015, 5 (46) : 36762 - 36765
  • [39] 'Click' Synthesis and Redox Properties of Triazolyl Cobalticinium Dendrimers
    Rapakousiou, Amalia
    Wang, Yanlan
    Belin, Colette
    Pinaud, Noel
    Ruiz, Jaime
    Astruc, Didier
    INORGANIC CHEMISTRY, 2013, 52 (11) : 6685 - 6693
  • [40] Click Synthesis and Redox Chemistry of Mono- and Heterobimetallic Triazolyl and Triazolium-Ferrocene and Cobalticinium Complexes
    Rapakousiou, Amalia
    Mouche, Claire
    Duttine, Mathieu
    Ruiz, Jaime
    Astruc, Didier
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (31) : 5071 - 5077
12345