107235-17-6

Basic information

• Product Name: 3-benzyl-5-methylbenzoxazol-2(3H)-one
• Synonyms: 3-benzyl-5-methylbenzoxazol-2(3H)-one
• CAS NO: 107235-17-6
• Molecular Weight: 239.274
• Mol File: 107235-17-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-benzyl-5-methylbenzoxazol-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyl-5-methylbenzoxazol-2(3H)-one(107235-17-6)
• EPA Substance Registry System: 3-benzyl-5-methylbenzoxazol-2(3H)-one(107235-17-6)

Safety Data

• Hazardous Substances Data: 107235-17-6(Hazardous Substances Data)

Upstream product

• 95-84-1 3-amino-4-hydroxytoluene 
• 19430-24-1 4-methyl-2-[(phenylmethylene)amino]phenol 
• 100-52-7 benzaldehyde 
• 77434-53-8 2-(benzylamino)-4-methylphenol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 10531-78-9 5-methyl-1,3-benzoxazole 
• 108-88-3 toluene 
• 22876-15-9 5-methylbenzo[d]oxazol-2(3H)-one 
• 100-39-0 benzyl bromide 

Downstream Products

• 77434-53-8 2-(benzylamino)-4-methylphenol 

Relevant articles and documents

Design, Synthesis, and Biological Activity of New N -(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension

Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.

Optimization of N-benzyl-benzoxazol-2-ones as receptor antagonists of macrophage migration inhibitory factor (MIF)

The cytokine MIF is involved in inflammation and cell proliferation via pathways initiated by its binding to the transmembrane receptor CD74. MIF also exhibits keto-enol tautomerase activity, believed to be vestigial in mammals. Starting from a 1 μM hit from virtual screening, substituted benzoxazol-2-ones have been discovered as antagonists with IC50 values as low as 7.5 nM in a tautomerase assay and 80 nM in a MIF-CD74 binding assay. Additional studies for one of the potent inhibitors demonstrated that it is not a covalent inhibitor of MIF and that it attenuates MIF-dependent ERK1/2 phosphorylation in human synovial fibroblasts.

Anti-allergic or anti-inflammatory substituted (hetero)-aralkylamino-ortho-phenols

Compounds of the general formula (I) or a pharmaceutically acceptable salt or solvate thereof;, wherein R1 is straight or branched C1-6alkyl, halo, nitro, cyano, hydroxy, or COR6 wherein R6 is straight or branch