1208307-97-4

Upstream product

• 1208307-91-8 (S)-4-((9-methoxy-4-tosyl-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-3-yl)methyl)phenol 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 1208307-84-9 (S)-N-(2-(benzyloxy)-3-methoxybenzyl)-N-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)-4-methylbenzenesulfonamide 
• 1208307-87-2 (S)-N-(1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl)-N-(2-hydroxy-3-methoxybenzyl)-4-methylbenzenesulfonamide 
• 1208307-81-6 methyl (S)-2-(N-(2-(benzyloxy)-3-methoxybenzyl)-4-methylphenylsulfonamido)-3-(4-(benzyloxy)phenyl)propanoate 
• 175214-62-7 C₂₄H₂₅NO₅S 
• 52508-44-8 2-benzyloxy-3-hydroxymethyl-1-methoxybenzene 
• 34805-17-9 methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 2011-06-5 2-benzyloxy-3-methoxybenzaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 

Relevant academic research and scientific papers

Amino acids derived benzoxazepines: Design, synthesis and antitumor activity

Two series of new benzoxazepines substituted with different alkyl amino ethyl chains were synthesized comprising synthetic steps of inter and intramolecular Mitsunobu reaction, lithium aluminium hydride (LAH) reduction, debenzylation, bimolecular nucleophilic substitution (SN2) reaction. The present study investigates the effect of a tyrosine-based benzoxazepine derivative in human breast cancer cells MCF-7 and MDA-MB-231 and in breast cancer animal model. The anti-proliferative effect of 15a on MCF-7 cells was associated with G1 cell-cycle arrest. This G1 growth arrest was followed by apoptosis as 15a dose dependently increased phosphatidylserine exposure, PARP cleavage and DNA fragmentation that are hallmarks of apoptotic cell death. Interestingly, 15a activated components of both intrinsic and extrinsic pathways of apoptosis characterized by activation of caspase-8 and -9, mitochondrial membrane depolarization and increase in Bax/Bcl2 ratio. However, use of selective caspase inhibitors revealed that the caspase-8-dependent pathway is the major contributor to 15a-induced apoptosis. Compound 15a also significantly reduced the growth of MCF-7 xenograft tumors in athymic nude mice. Together, 15a could serve as a base for the development of a new group of effective breast cancer therapeutics.

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

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 G0/G1 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 16 mg kg-1 dose at 30 days of treatment. The identified most active compounds of the series have specific advantages as anti-cancer agent in breast cancer than tamoxifen.