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

页码：71 / 79

页数：9

共 50 条

[31] Highly efficient synthesis of polyfluorinated dendrons suitable for click chemistry
Koelmel, Dominik K.
Nieger, Martin
Braese, Stefan
RSC ADVANCES, 2015, 5 (46) : 36762 - 36765
[32] 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
[33] Highly Efficient "Grafting onto" a Polypeptide Backbone Using Click Chemistry
Engler, Amanda C.
Lee, Hyung-il
Hammond, Paula T.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) : 9334 - 9338
[34] Synthesis, the success Click-Chemistry
Kunz, Doris
CHEMIE IN UNSERER ZEIT, 2009, 43 (04) : 224 - 230
[35] Efficient Eco-friendly Solvent-free Flash Synthesis of Novel Bis and Tris(1,2,3-Triazolyl)Esters Using Click Chemistry
Ranjbar-Karimi, Reza
Mehrafarin, Ali
Mahyari, Amir
Mehrabi, Hossein
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 28 (02) : 279 - 286
[36] FACILE SYNTHESIS OF MONO- AND POLYTOPIC β-CYCLODEXTRIN AROMATIC ALDEHYDES BY CLICK CHEMISTRY
Guo, Hongyu
Yang, Fafu
Zhang, Yingmei
Di, Xingdong
SYNTHETIC COMMUNICATIONS, 2015, 45 (03) : 338 - 347
[37] A Mild, Facile, One-Pot Synthesis of Zinc Azido Porphyrins as Substrates for Use in Click Chemistry
Bryden, Francesca
Boyle, Ross W.
SYNLETT, 2013, 24 (15) : 1978 - 1982
[38] Application of click chemistry in the synthesis of bidentate ligands and their metal complexes
Ugwu, David Izuchukwu
Conradie, Jeanet
POLYHEDRON, 2023, 235
[39] Click Glycosylation for the Synthesis of 1,2,3-Triazole-Linked Picropodophyllotoxin Glycoconjugates and Their Anticancer Activity
Zi, Cheng-Ting
Yang, Liu
Gao, Wei
Li, Yan
Zhou, Jun
Ding, Zhong-Tao
Hu, Jiang-Miao
Jiang, Zi-Hua
CHEMISTRYSELECT, 2017, 2 (18): : 5038 - 5044
[40] FACILE FUNCTIONALIZATION OF POLYROTAXANES VIA CLICK CHEMISTRY
Wu Jiayan
Gao Chao
ACTA POLYMERICA SINICA, 2010, (04) : 496 - 500

← 1 2 3 4 5 →