701-16-6

Usage

Uses

Used in Pharmaceutical Industry:
5-Fluoro-2-methylbenzoxazole is used as a reactant in the preparation of benzothiadiazine compounds, which serve as CD73 inhibitors. CD73 is an enzyme involved in the production of adenosine, a molecule with immunosuppressive and anti-inflammatory properties. Inhibition of CD73 can modulate the immune response and has potential therapeutic applications in the treatment of various diseases, including cancer and autoimmune disorders.

InChI:InChI=1/C8H6FNO/c1-5-10-7-4-6(9)2-3-8(7)11-5/h2-4H,1H3

Upstream product

• 399-97-3 2-amino-4-fluorophenol 
• 108-24-7 acetic anhydride 
• 394-33-2 2-nitro-4-fluorophenol 
• 371-41-5 4-Fluorophenol 
• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 40703-40-0 5-fluoro-2-methyl-6-nitrobenzo[d]oxazole 

Relevant academic research and scientific papers

ANDROGEN RECEPTOR ANTAGONISTS

Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.

Multicatalytic Beckmann rearrangement of 2-hydroxylarylketone oxime: Switchable synthesis of benzo[d]oxazoles and N-(2-hydroxylaryl)amides

A switchable synthesis route is developed for benzo[d]oxazole derivatives and (2-hydroxylaryl)benzamide from 2-hydroxylbenzeneketoxime using organomolecules (BOP-Cl, and CNC) and Lewis acid cocatalyzed Beckmann rearrangement (BR) reaction. Further, this reaction is switched using different organocatalysts.

BENZOTHIADIAZINE COMPOUNDS

The invention is directed to substituted benzothiadiazine derivatives. Specifically, the invention is directed to compounds according to Formula (I):wherein R, R1, R2, R3, R4 and R5 are as defined herein. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, autoimmune diseases, infections, atherosclerosis, and ischemia-reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

Mass spectra of halogenostyrylbenzoxazoles

Several series of styrylbenzoxazoles of general formula XC 6H3(NCO)CHCHC6H4Y [X = F, Cl or Br; Y = H, F, Cl, Br, CH3 or CH3O] have been investigated by positive ion electrospray and electron ionization mass spectrometry. These compounds, many of which are biologically active or have pharmaceutical potential, show in their electrospray spectra strong peaks for MH+ ions, which undergo relatively little fragmentation. The electron ionization spectra are extremely clean, being dominated by the loss of an atom or radical, Y, from the ortho position of the pendant ring, by a rearrangement that may be interpreted as a proximity effect. The resultant [M-Y]+ ions are exceptionally stable and rarely undergo further fragmentation. The analytical value of this proximity effect, which is analogous to intramolecular aromatic substitution, in revealing the presence of a substituent in the pendant ring and determining its position, is emphasized. Elimination of a species (including H or F) derived from an ortho substituent in the pendant ring occurs even when apparently more favourable alternative fragmentation is possible by direct cleavage of the CX bond (X = Cl or Br) in the benzoxazole ring.

FLUORO-SUBSTITUTED BENZOXAZOLE POLYMETHINE DYES

Disclosed are reactive polyfluoro benzoxazole polymethine dyes that are useful for labelling and detecting biological and other materials. The dyes are of formula (I): in which X is selected from the group consisting of -O-, -S- and at least one of groups