245095-50-5

Basic information

• Product Name: 5-(bromomethyl)-3-methyl-1,3-benzoxazol-2-one
• Synonyms: 5-(bromomethyl)-3-methyl-1,3-benzoxazol-2-one
• CAS NO: 245095-50-5
• Molecular Weight: 242.072
• Mol File: 245095-50-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-(bromomethyl)-3-methyl-1,3-benzoxazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(bromomethyl)-3-methyl-1,3-benzoxazol-2-one(245095-50-5)
• EPA Substance Registry System: 5-(bromomethyl)-3-methyl-1,3-benzoxazol-2-one(245095-50-5)

Safety Data

• Hazardous Substances Data: 245095-50-5(Hazardous Substances Data)

Upstream product

• 88882-28-4 3,5-dimethylbenzo[d]oxazol-2(3H)-one 
• 22876-15-9 5-methylbenzo[d]oxazol-2(3H)-one 
• 95-84-1 3-amino-4-hydroxytoluene 

Downstream Products

• 903556-83-2 C₉H₈N₄O₂ 

Relevant articles and documents

Combretastatin A-4 analogues with benzoxazolone scaffold: Synthesis, structure and biological activity

In order to design and synthesize a new class of heterocyclic analogues of natural combretastatin A-4 and its synthetic derivative AVE8062, the benzoxazolone ring was selected as a scaffold for a bioisosteric replacement of the ring B of both molecules. A library of 28 cis- and trans-styrylbenzoxazolones was obtained by a modified Wittig reaction under Boden's conditions. Structures of the newly synthesized compounds bearing the 3,4,5-trimethoxy-, 3,4-dimethoxy-, 3,5-dimethoxy-, and 4-methoxystyryl fragment at position 4, 5, 6 or 7 of benzoxazolone core were determined on the basis of spectral and X ray data. The in vitro cytotoxicity of styrylbenzoxazolones against different cell lines was examined. Stilbene derivative 16Z, (Z)-3-methyl-6-(3,4,5-trimethoxystyryl)-2(3H)-benzoxazolone, showed highest antiproliferative potential of the series, with IC50 of 0.25 μM against combretastatin resistant cell line HT-29, 0.19 μM against HepG2, 0.28 μM against EA.hy926 and 0.73 μM against K562 cells. Furthermore, the results of flow cytometric analysis confirmed that 16Z induced cell cycle arrest in G2/M phase in the cell lines like combretastatin A-4. This arrest is followed by an abnormal exit of cells from mitosis without cytokinesis into a pseudo G1-like multinucleate state leading to late apoptosis and cell death. Accordingly, synthetic analogue 16Z was identified as the most promising potential anticancer agent in present study, and was selected as lead compound for further detailed investigations.

Multicyclic bis-amide MMP inhibitors

The present invention relates generally to bis-amide group containing pharmaceutical agents, and in particular, to multicyclic bis-amide MMP-13 inhibitor compounds. More particularly, the present invention provides a new class of MMP-13 inhibiting compounds, containing a pyrimidinyl bis-amide group in combination with a heterocyclic moiety, that exhibit an increased potency and solubility in relation to currently known bis-amide group containing MMP-13 inhibitors.