154235-77-5

Basic information

• Product Name: benzo[d]oxazole-6-carboxylic acid
• Synonyms: benzo[d]oxazole-6-carboxylic acid;1,3-Benzoxazole-6-carboxylic acid;Benzoxazole-6-carboxylic Acid;6-Benzoxazolecarboxylic acid
• CAS NO: 154235-77-5
• Molecular Formula: C₈H₅NO₃
• Molecular Weight: 163.13
• Mol File: 154235-77-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 280-290 °C (sublm)(Press: 16 Torr)
• Boiling Point: 350.094 °C at 760 mmHg
• Flash Point: 165.531 °C
• Appearance: /
• Density: 1.455 g/cm³
• Storage Temp.: 2-8°C
• PKA: 3.60±0.30(Predicted)
• CAS DataBase Reference: benzo[d]oxazole-6-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: benzo[d]oxazole-6-carboxylic acid(154235-77-5)
• EPA Substance Registry System: benzo[d]oxazole-6-carboxylic acid(154235-77-5)

Safety Data

• Hazardous Substances Data: 154235-77-5(Hazardous Substances Data)

Usage

Description

Benzo[d]oxazole-6-carboxylic acid is an organic compound with the molecular formula C8H5NO3. It is a heterocyclic compound featuring a benzene ring fused to an oxazole ring, with a carboxylic acid group attached at the 6th position. This molecule is known for its unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
Benzo[d]oxazole-6-carboxylic acid is used as a key reactant in the design, synthesis, and development of novel pharmaceutical compounds. Its unique structure allows for the creation of various derivatives with potential therapeutic applications.
Used in Medicinal Chemistry:
Benzo[d]oxazole-6-carboxylic acid is utilized as a building block in the structure-activity relationship (SAR) studies of different drug candidates. By understanding how the structure of this compound affects its biological activity, researchers can optimize the design of new drugs with improved efficacy and safety profiles.
Used in the Synthesis of α7 Nicotinic Acetylcholine Receptor Agonists:
Benzo[d]oxazole-6-carboxylic acid is used as a reactant in the synthesis of azabicyclic aryl amides, which are known to act as α7 nicotinic acetylcholine receptor agonists. These agonists have potential therapeutic applications in the treatment of various neurological and cognitive disorders, such as Alzheimer's disease, schizophrenia, and attention deficit hyperactivity disorder (ADHD).

Upstream product

• 2374-03-0 4-aminosalicylic acid 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1393746-99-0 C₂₂H₂₇N₃O₃ 
• 594839-88-0 2-(3,5-dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid 
• 198554-21-1 4-[1-(1,3-benzoxazol-6-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine 

Relevant articles and documents

Nickel-catalyzed C-H arylation of azoles with haloarenes: Scope, mechanism, and applications to the synthesis of bioactive molecules

Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. We have established that Ni(OAc)2/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)2/dppf (dppf=1,1′-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, we discovered a new protocol for the present coupling using Mg(OtBu)2 as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodology has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity). Copyright

Design, synthesis and evaluation of benzoheterocycle analogues as potent antifungal agents targeting CYP51

To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compound 1, a series of benzoheterocycle analogues were designed, synthesized and evaluated for their in vitro antifungal activity. The most promising compounds 13s and 14a exhibited excellent antifungal activity against C. albicans, C. neoformans, A. fumigatus and fluconazole-resistant C. albicans strains, that was superior or comparable to those of the reference drugs fluconazole and voriconazole. GC–MS analyses suggested that the novel compound 13s might have a similar mechanism to fluconazole by inhibiting fungal lanosterol 14α-demethylase (CYP51). Furthermore, compounds 13s and 14a exhibited low inhibition profiles for various human cytochrome P450 isoforms as well as excellent blood plasma stability.

Quinuclidine-substituted hetero-bicyclic aromatic compounds for the treatment of disease

The invention provides compounds of Formula I: wherein W0 is a bicyclic moiety and is These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful to treat diseases or conditions in which α7 is known to be involved.