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

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Abstract

An efficient protocol for the synthesis of tubulin polymerization inhibitor, 9-azido-α-noscapine 2h from 9-amino-α-noscapine 2g is developed using mild reaction conditions (t-butyl nitrite/trimethylsilyl azide in acetonitrile at room temperature). Operational simplicity, high product yield without formation of any side products are the advantages of this protocol. Further copper catalyzed click reactions of 9-azido-α-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-α-noscapine from 9-amino-α-noscapine under mild reaction conditions; was further derivatized to triazoles using click chemistry.

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Acknowledgments

Authors thank the Department of Biotechnology, Ministry of Science and Technology, India for financial support (BT/Indo-Aus/07/06/2013). NKM and PRN are thankful to CSIR and UGC, respectively, for senior research fellowships.

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Authors and Affiliations

  1. Organic Chemistry Division-II (C P C Division), CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, 500007, India

    Naresh Kumar Manchukonda, Praveen Kumar Reddy Nagireddy & Srinivas Kantevari

  2. Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India

    Balasubramanian Sridhar

  3. Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India

    Srinivas Kantevari

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  1. Naresh Kumar Manchukonda
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  2. Praveen Kumar Reddy Nagireddy
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Correspondence to Srinivas Kantevari.

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Manchukonda, N.K., Nagireddy, P.K.R., Sridhar, B. et al. Synthesis and click reaction of tubulin polymerization inhibitor 9-azido-α-noscapine. Res Chem Intermed 43, 2457–2469 (2017). https://doi.org/10.1007/s11164-016-2773-7

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