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  • Anti-tumor activity of a new series of benzoxazepine derivatives in breast cancer.

Anti-tumor activity of a new series of benzoxazepine derivatives in breast cancer.

Bioorganic & medicinal chemistry letters (2009-11-26)
Krishnananda Samanta, Bandana Chakravarti, Jitendra Kumar Mishra, Shailendra Kumar Dhar Dwivedi, Lakshma Vadithe Nayak, Preeti Choudhry, Hemant Kumar Bid, Rituraj Konwar, Naibedya Chattopadhyay, Gautam Panda
ABSTRACT

A series of new benzoxazepine derivatives substituted with different alkoxy and aryloxy group were synthesized comprising synthetic steps of Mitsunobu reaction, lithium aluminum hydride (LAH) reduction, followed by debenzylation and finally intramolecular Mitsunobu cyclization. The new benzoxazepines specifically inhibited growth of breast cancer cell lines, MCF-7 and MDA-MB-231, but lack cytotoxicity to normal HEK-293 cells. The cell growth inhibition induced by the active compounds was due to cell cycle arrest at G(0)/G(1) phase. The active compound could cause significant reduction in tumor volume of MCF-7 xenograft tumor in nude mice model and their activity was comparable to that of tamoxifen citrate at 16mgkg(-1) dose at 30days of treatment. The identified most active compounds of the series have specific advantages as anti-cancer agent in breast cancer than tamoxifen.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Lithium aluminum hydride, ≥97.0% (gas-volumetric)
Sigma-Aldrich
Lithium aluminum hydride, pellets, reagent grade, 95%
Sigma-Aldrich
Lithium aluminum hydride, hydrogen-storage grade
Sigma-Aldrich
Lithium aluminum hydride solution, 2.0 M in THF
Sigma-Aldrich
Lithium aluminum hydride solution, 2.3 M in 2-methyltetrahydrofuran
Sigma-Aldrich
Lithium aluminum hydride solution, 1.0 M in diethyl ether
Sigma-Aldrich
Lithium aluminum hydride solution, 1.0 M in THF
Sigma-Aldrich
Lithium aluminum hydride solution, 0.5 M in 2-methoxyethyl ether
Sigma-Aldrich
Lithium aluminum hydride, powder, reagent grade, 95%