67081-68-9

Usage

Physical appearance

White crystalline powder.

Solubility

Soluble in ethanol and acetone, slightly soluble in water.

Use in pharmaceuticals

Used in the synthesis of various pharmaceutical drugs.

Use in organic synthesis

Serves as an intermediate in organic synthesis.

Therapeutic properties

Exhibits anti-inflammatory and analgesic properties.

Potential application

May be a candidate for the development of new therapeutic drugs.

Upstream product

• 1196-79-8 2,5-Dimethyl-1H-indole 
• 2437-73-2 2,3,6-trimethylquinoline 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 32833-96-8 N,N-dimethyloxamic acid 
• 103-89-9 4-Methylacetanilide 
• 2050-43-3 N-(2,4-dimethylphenyl)acetamide 
• 117039-81-3 1-acetyl-1,2-dihydro-2,5-dimethyl-2-hydroxy-3H-indol-3-one 
• 117039-80-2 2,3,6-trimethyl-4(1H)-quinolinone 
• 201230-82-2 carbon monoxide 

Downstream Products

• 101423-49-8 3-(2,4-dichloro-phenyl)-2,6-dimethyl-3H-quinazolin-4-one 
• 4343-28-6 2,6-dimethyl-3-(4-nitro-phenyl)-3H-quinazolin-4-one 
• 1123684-99-0 4-chloro-2-[(E)-2-(4-chlorophenyl)ethenyl]-6-methylquinazoline 

Relevant academic research and scientific papers

Synthesis, molecular modeling of N-acyl benzoazetinones and their docking simulation on fungal modeled target

A series of stable N-acyl benzoazetinones have been synthesized in moderate to good yields (58–85%) from easily available substrates such as 2-(N-acyl) amino benzoic acids through intramolecular amidation under mild conditions. These geometry-optimized benzoazetinones were docked in the model target of P450, class CYP53A15, a benzoate 4-monooxygenase abundantly found in the genome of ascomycetes and Basidiomycetes classes of pathogenic fungi. Low per residue root-mean-square deviation (RMSD) of modeled structure of the enzyme indicated similar topology as template (4D6Z.pdb). Observed score judges site-specific docking, and the interaction of quantum mechanically optimized benzoazetinone derivatives with the target enzyme. These results suggest that 3i is the best antifungal agent. The specific hydrophobic substituent in the benzoazetinones contributed to the stability of ligand–target complex. Overall, the study provided insight into the specificity of the site-specific interactions, thereby, facilitating the possibility of development of broad-spectrum antifungal agents against opportunistic and infectious fungi.

Palladium-catalyzed C-H bond carboxylation of acetanilides: An efficient usage of N,N-dimethyloxamic acid as the carboxylate source

N,N-Dimethyloxamic acid can be successfully employed as a carboxylate precursor in the palladium-catalyzed direct C-H carboxylation of acetanilides. The reaction proceeds smoothly under mild conditions over a broad range of substrates with high functional group tolerance, affording substituted N-acyl anthranilic acids in moderate to high yields.

Synthesis and evaluation of quinazolines as inhibitors of the bacterial cell division protein FtsZ

The bacterial cell division protein FtsZ is one of many potential targets for the development of novel antibiotics. Recently, zantrin Z3 was shown to be a cross-species inhibitor of FtsZ; however, its specific interactions with the protein are still unknown. Herein we report the synthesis of analogues that contain a more tractable core structure and an analogue with single-digit micromolar inhibition of FtsZs GTPase activity, which represents the most potent inhibitor of Escherichia coli FtsZ reported to date. In addition, the zantrin Z3 core has been converted to two potential photo-cross-linking reagents for proteomic studies that could shed light on the molecular interactions between FtsZ and molecules related to zantrin Z3.

Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: Expedient routes to anthranilic acids, oxazolinones, and quinazolinones

A Pd(II)-catalyzed reaction protocol for the carboxylation of ortho-C-H bonds in anilides to form N-acyl anthranilic acids has been developed. This reaction procedure provides a novel and efficient strategy for the rapid assembly of biologically and pharmaceutically significant molecules, such as benzoxazinones and quinazolinones, from simple anilides without installing and removing an external directing group. The reaction conditions are also amenable to the carboxylation of N-phenyl pyrrolidinones. A monomeric palladacycle containing p-toluenesulfonate as an anionic ligand has been characterized by X-ray crystallography, and the crucial role of p-toluenesulfonic acid in the activation of C-H bonds in the presence of carbon monoxide is discussed. Identification of two key intermediates, a mixed anhydride and benzoxazinone formed by reductive elimination from organometallic Ar(CO)Pd(II)-OTs species, provides mechanistic evidence for a dual-reaction pathway.

Phosphodiesterase 4-inhibiting diazepinoindolones

The present invention presents compounds that inhibit phosphodiesterase 4 having Formula (I). The present invention also provides methods of using the compounds of Formula (I) to prevent or treat asthma, atopic dermatitis, rheumatoid arthritis, inflammatory bowel disorders, pulmonary hypertension, liver injury, bone loss, septic shock, or multiple sclerosis, and to pharmaceutical compositions that contain the compounds of Formula (I).

1H and 13C NMR spectral studies of some 4H-3,1-benzoxazin-4-ones and their 2-acylaminobenzoic acid precursors

The 1H and 13C NMR spectra of twelve 4H-3,1-benzoxazine-4-ones and of their acylaminobenzoic acid precursors are presented. Differentiation between these two series of compounds is best achieved through the characteristic JCH coupling interactions in the high frequency carbonyl region. Some 4H-pyrido[2,3-d][1,3]oxazin-4-ones have also been studied and some earlier literature assignments revised.

Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds

The chemical synthesis of three close analogues (2-4) of N10-propargyl-5,8-dideazafolate (PDDF) is described. The quinazoline ring of 2 and 4 was constructed from the pivotal intermediate 9 in a novel and unambiguous manner during the final ste

Azepinoindole Synthesis from a 1,2,3,4-Tetrahydro-9(10H)-acridinone and Sodium Dichloroisocyanurate or Singlet Oxygen

Sodium dichloroisocyanurate (4) acts on 7-methyl-1,2,3,4-tetrahydro-9(10H)-acridinone (1) to give principally either cis-1,2-diol 2 or azepinoindole 3, by suitable choice of reactant proportions. 2,3,6-Trimethyl-4(1H)-quinolinone (6) yields a novel, methylene-bridged, oxygenated dimer 9, while with excess 4 the chief product is the 1,2-dihydro-3H-indol-3-one 7. 6-Methyl-2-phenyl-4(1H)-quinolinone (12) initially gives the 3-chloro derivative 14, which then reacts further with 4, yielding chlorine-free 6-methyl-2-phenyl-4H-3,1-benzoxazin-4-one (16).The sensitized photooxidation of acridinone 1 furnishes azepinoindole 3 en route to dicarboxylic acid 5; upon similar treatment, quinolinone 6 provides the analogous indolone 7.Reaction pathways to account for the results are presented.N-Halo imide 4 offers advantages over the more conventional NaOCl in synthesis as illustrated also with a "one-pot" Hofmann degradation of 4-chlorobenzamide.