3889-13-2

Usage

Uses

Used in Chemical Reactions and Organic Synthesis:
5-NITRO-1,3-BENZOXAZOL-2(3H)-ONE is used as a reactant in various chemical reactions and organic synthesis processes, contributing to the formation of complex organic molecules and compounds.
Used as a Pharmaceutical Intermediate:
In the pharmaceutical industry, 5-NITRO-1,3-BENZOXAZOL-2(3H)-ONE is utilized as an intermediate in the synthesis of various drugs, playing a crucial role in the development of new medicinal compounds.
Used in the Production of Dyes and Pigments:
5-NITRO-1,3-BENZOXAZOL-2(3H)-ONE is employed in the manufacturing process of certain dyes and pigments, contributing to the coloration and properties of these products.
Used in Biological and Pharmacological Research:
5-NITRO-1,3-BENZOXAZOL-2(3H)-ONE is used as a subject of study in biological and pharmacological research, exploring its potential antifungal and antibacterial properties for possible applications in medicine and other fields.
Used in Antifungal and Antibacterial Applications:
5-NITRO-1,3-BENZOXAZOL-2(3H)-ONE is being investigated for its potential use as an antifungal and antibacterial agent, which could be beneficial in treating infections and developing new antimicrobial therapies.

InChI:InChI=1/C7H4N2O4/c10-7-8-5-3-4(9(11)12)1-2-6(5)13-7/h1-3H,(H,8,10)

Upstream product

• 75-44-5 phosgene 
• 99-57-0 2-hydroxy-5-nitroaniline 
• 43112-62-5 (2-Hydroxy-5-nitro-phenyl)-carbamic acid phenyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1659-31-0 2,2'-dipyridyl carbonate 
• 2851-07-2 2-methylsulfanyl-5-nitro-benzooxazole 
• 503-38-8 trichloromethyl chloroformate 
• 541-41-3 chloroformic acid ethyl ester 
• 1245209-77-1 2-hydroxy-5-nitrobenzoyl azide 
• 103029-82-9 5-nitro-3-acetylbenz[d]oxazol-2(3H)-one 
• 19213-72-0 ethyl 1-imidazolecarboxylate 
• 1202680-24-7 phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 

Downstream Products

• 101084-60-0 3-methyl-5-nitrobenzo[d]oxazol-2(3H)-one 
• 99420-21-0 3-benzenesulfonyl-5-nitro-3H-benzoxazol-2-one 
• 106590-64-1 5-nitro-3-(toluene-4-sulfonyl)-3H-benzoxazol-2-one 
• 14733-77-8 5-amino-2-benzoxazolinone 
• 33703-89-8 3-(3-chloropropyl)-5-nitro-3H-benzoxazol-2-one 
• 22876-21-7 4-nitro-1,3-benzoaxazolidine-2-thione 
• 787-03-1 C₆H₃NO₂CO₂NSCFCl₂ 
• 554-68-7 triethylamine hydrochloride 
• 99584-09-5 5-amino-3-methyl-1,3-benzoxazol-2(3H)-one 

Relevant academic research and scientific papers

Synthesis and evaluation of technetium-99m labelled 1-(2-methoxyphenyl)piperazine derivative for single photon emission computed tomography imaging for targeting 5-HT1A

Quantitative changes in expression level of 5HT1A are somewhere related to common neurological disorders such as anxiety, major depression and schizophrenia. We have designed EDTA conjugated SPECT imaging probe for localization of 5HT1A/s

[99mTc-BBPA]: A possible SPECT agent to understand the role of 18-kDa translocator protein (PBR/TSPO) during neuro-glial interaction

The translocator protein (TSPO, 18 kDa) is one of the most promising biomarker to understand the role of neuroinflammation in human as well as in different animal species. Here we report a new TSPO-selective ligand 2-(5-(2-(bis(pyridin-2-yl methyl)amino)acetamido)-2-oxobenzo[d] oxazol-3(2H)-yl)-N-methyl-N-phenylacetamide, BBPA, which is supposed to be a potential probe to understand the role of TSPO in neuro-glial interaction through SPECT modality.

Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3

Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.

Identification and characterization of benzo[d]oxazol-2(3H)-one derivatives as the first potent and selective small-molecule inhibitors of chromodomain protein CDYL

Chemical probes of epigenetic ‘readers’ of histone post-translational modifications (PTMs) have become powerful tools for mechanistic and functional studies of their target proteins in physiology and pathology. However, only limited ‘reader’ probes have been developed, which restricted our understanding towards these macromolecules and their roles in cells or animals. Here, we reported a structure-guided approach to develop and characterize benzo [d]oxazol-2(3H)-one analogs as the first potent and selective small-molecule inhibitors of chromodomain Y-like (CDYL), a histone methyllysine reader protein. The binding conformation between the chromodomain of CDYL and the modified peptidomimetics was studied via molecular docking and dynamic simulations, facilitating subsequent virtual screening of tens of hits from Specs chemical library validated by SPR technique (KD values: from 271.1 μM to 5.4 μM). Further design and synthesis of 43 compounds helped to interpret the structure-activity relationship (SAR) that lead to the discovery of novel small-molecule inhibitors of CDYL. Compound D03 (KD: 0.5 μM) was discovered and showed excellent selectivity among other chromodomain proteins, including CDYL2 (>140 folds), CDY1 (no observed binding) and CBX7 (>32 folds). Moreover, we demonstrated that D03 engaged with endogenous CDYL in a dose-dependent manner, and perturbed the recruitment of CDYL onto chromatin, resulting in transcriptional derepression of its target genes. Finally, the results showed that D03 promoted the development and branching of neurodendrites by inhibiting CDYL in hippocampal and cortical cultured neurons. This study not only discovers the first selective small-molecule inhibitors of CDYL, but provids a new chemical tool to intervene the dynamic nature of bio-macromolecules involved in epigenetic mechanism.

SUBSTITUTED BICYCLE HETEROCYCLIC DERIVATIVES USEFUL AS ROMK CHANNEL INHIBITORS

Disclosed are compounds of Formula (I) or a salt thereof, wherein R1 is (II) or (III); each W is independently NR1b or O; Z is a bond or CHR1d; and R1, R2, Rd, R3, L1, L2, R1a, R1b, R1c, and n are define herein. Also disclosed are methods of using such compounds as inhibitors of ROMK, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating cardiovascular diseases.

SUBSTITUTED NITROGEN CONTAINING COMPOUNDS

Disclosed are compounds of Formula (I): or a salt thereof, Formula (II) wherein R1 is: or; each W is independently NR1b or O; Z is a bond or CHR1d; and R1, R2, Rd, R3a, R3b, L1, B, V, Y, and n are defined herein. Also disclosed are methods of using such compounds as inhibitors of ROMK, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating cardiovascular diseases.

Modified benzoxazolone derivative as 18-kDa TSPO ligand

We have synthesized six new congeners of acetamidobenzoxazolone for Translocator Protein [18 kDa, TSPO] imaging. The best in vitro binding affinity (10.8?±?1.2?nm) for TSPO was found for N-methyl-2-(5-(naphthalen-1-yl)-2-oxobenzo[d]oxazol-3(2H)-yl)-N-phen

Discovery of potent IDO1 inhibitors derived from tryptophan using scaffold-hopping and structure-based design approaches

Indoleamine 2,3-dioxygenase 1 (IDO1) is frequently hijacked by tumors to escape the host immune response, and the enzyme is now firmly established as an attractive target for cancer immunotherapy. To identify novel IDO1 inhibitors suitable for drug development, a scaffold-hopping strategy combined with the average electrostatic potentials calculation was ultilized to design novel benzoxazolinone derivatives. Among these, compounds 7e, 7f and 9c exhibited the inhibitory potency in the low micromolar range and displayed negligible level of cytotoxicity against HeLa cells. Treatment with these three compounds promoted the proliferation of T lymphocyte and led to the dramatic decrease of regulatory T cells in the B16F1 cells and na?ve T cells co-culture system. Subsequent spectroscopic experiments suggested that these benzoxazolinones formed a coordinate bond with the heme iron to stabilize the complex. This study suggested that the benzoxazolinone was an interesting scaffold for discovering novel IDO1 inhibitors, and these compounds are attractive candidates for further development.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of Formulas I-VI, including pharmaceutically acceptable salts thereof, and compositions and methods for treating human immunodeficiency virus (HIV) infection are set forth. Formula I is exemplified below: Formula (i)

Facile Synthesis of Benzo[ d ]azol-2(3 H)-ones Using 2-Phenoxycarbonyl-4,5-dichloropyridazin-3(2 H)-one as Green CO Source

Developing eco-friendly, stable, and easy-to-handle acyl sources is of great importance in synthetic and green chemistry. This study describes the synthesis of benzo[d]azol-2(3H)-ones such as benzo[d]thiazol-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, and benzo[d]imidazol-2(3H)-ones using 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one in one pot. The reaction reported is carried out under neutral or acidic conditions in the presence of zinc or sodium bicarbonate to give the corresponding heterocycles in good to excellent yields. The reaction uses a solid stable carbonyl source that is a recyclable functional-group carrier, pyridazin-3(2H)-one.