Synthesis and click reaction of tubulin polymerization inhibitor 9-azido-α-noscapine

Synthesis and click reaction of tubulin polymerization inhibitor 9-azido-α-noscapine Res Chem Intermed (2017) 43:2457–2469 DOI 10.1007/s11164-016-2773-7 Synthesis and click reaction of tubulin polymerization inhibitor 9-azido-a-noscapine 1 1 • • Naresh Kumar Manchukonda Praveen Kumar Reddy Nagireddy 2 1,3 Balasubramanian Sridhar Srinivas Kantevari Received: 8 August 2016 / Accepted: 8 October 2016 / Published online: 24 October 2016 Springer Science+Business Media Dordrecht 2016 Abstract An efficient protocol for the synthesis of tubulin polymerization inhibitor, 9-azido-a-noscapine 2h from 9-amino-a-noscapine 2g is developed using mild reaction conditions (t-butyl nitrite/trimethylsilyl azide in acetonitrile at room temperature). Opera- tional simplicity, high product yield without formation of any side products are the advan- tages of this protocol. Further copper catalyzed click reactions of 9-azido-a-noscapine 2h with alkynes 6a–f resulted 9-triazolyl noscapinoids 7a–f resulted in excellent yields. Graphical Abstract Developed an amicable protocol for the synthesis of 9-azido-a- noscapine from 9-amino-a-noscapineunder mild reaction conditions; was further derivatized to triazoles using click chemistry. Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2773- 7) contains supplementary material, which is available to authorized users. & Srinivas Kantevari kantevari@yahoo.com; kantevari@gmail.com Organic Chemistry Division-II (C P C Division), CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana 500007, India Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Synthesis and click reaction of tubulin polymerization inhibitor 9-azido-α-noscapine

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Publisher
Springer Journals
Copyright
Copyright © 2016 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2773-7
Publisher site
See Article on Publisher Site

Abstract

Res Chem Intermed (2017) 43:2457–2469 DOI 10.1007/s11164-016-2773-7 Synthesis and click reaction of tubulin polymerization inhibitor 9-azido-a-noscapine 1 1 • • Naresh Kumar Manchukonda Praveen Kumar Reddy Nagireddy 2 1,3 Balasubramanian Sridhar Srinivas Kantevari Received: 8 August 2016 / Accepted: 8 October 2016 / Published online: 24 October 2016 Springer Science+Business Media Dordrecht 2016 Abstract An efficient protocol for the synthesis of tubulin polymerization inhibitor, 9-azido-a-noscapine 2h from 9-amino-a-noscapine 2g is developed using mild reaction conditions (t-butyl nitrite/trimethylsilyl azide in acetonitrile at room temperature). Opera- tional simplicity, high product yield without formation of any side products are the advan- tages of this protocol. Further copper catalyzed click reactions of 9-azido-a-noscapine 2h with alkynes 6a–f resulted 9-triazolyl noscapinoids 7a–f resulted in excellent yields. Graphical Abstract Developed an amicable protocol for the synthesis of 9-azido-a- noscapine from 9-amino-a-noscapineunder mild reaction conditions; was further derivatized to triazoles using click chemistry. Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2773- 7) contains supplementary material, which is available to authorized users. & Srinivas Kantevari kantevari@yahoo.com; kantevari@gmail.com Organic Chemistry Division-II (C P C Division), CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana 500007, India Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 24, 2016

References

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