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

Manchukonda, Naresh; Nagireddy, Praveen; Sridhar, Balasubramanian; Kantevari, Srinivas

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.

TUBULINS; NOSCAPINE; CLICK chemistry; POLYMERIZATION; CHEMICAL synthesis; COPPER catalysts

Research on Chemical Intermediates, 2017, Vol 43, Issue 4, p2457

0922-6168

Academic Journal

10.1007/s11164-016-2773-7