35710-05-5

Usage

Uses

Used in Organic Synthesis:
N-Benzylisatoic anhydride is used as a reagent for the acylation of amines and alcohols, a process that is crucial in the formation of various organic compounds. Its strong acylating properties make it a preferred choice in this application.
Used in Pharmaceutical Production:
In the pharmaceutical industry, N-Benzylisatoic anhydride is utilized as a key intermediate in the synthesis of various drugs. Its reactivity and versatility in organic reactions contribute to the development of new and effective medications.
Used in Agrochemical Production:
N-Benzylisatoic anhydride also finds application in the agrochemical sector, where it serves as an intermediate in the synthesis of various agrochemicals, including pesticides and herbicides, enhancing crop protection and yield.

InChI:InChI=1/C15H11NO3/c17-14-12-8-4-5-9-13(12)16(15(18)19-14)10-11-6-2-1-3-7-11/h1-9H,10H2

Upstream product

• 75-44-5 phosgene 
• 6622-55-5 N-benzylanthranilic acid 
• 118-48-9 isatoic anhydride 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 758640-21-0 N-Benzylaniline 
• 201230-82-2 carbon monoxide 
• 1217-89-6 1-benzylisatin 
• 118-92-3 anthranilic acid 
• 124-38-9 carbon dioxide 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 91-73-6 N,N-dibenzylaniline 

Downstream Products

• 59103-54-7 1-Benzyl-2,1-benzothiazol-3(1H)-one 
• 108202-09-1 9-Benzyl-1,2,3,9-tetrahydro-pyrrolo[2,3-b]quinolin-4-one 
• 143884-48-4 10-Benzyl-3,4-dihydro-2H,10H-1-thia-10-aza-anthracen-9-one 
• 108202-15-9 11-Benzyl-1,2,3,4,5,11-hexahydro-azepino[2,3-b]quinolin-6-one 
• 117838-14-9 Benzyl-{2-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-phenyl}-amine 
• 117838-06-9 4-Methoxy-benzoic acid N'-(2-benzylamino-benzoyl)-hydrazide 
• 117838-12-7 Benzyl-[2-(5-phenyl-[1,3,4]oxadiazol-2-yl)-phenyl]-amine 
• 117838-04-7 Benzoic acid N'-(2-benzylamino-benzoyl)-hydrazide 
• 73480-61-2 2-Benzylamino-N-(2-hydroxy-butyl)-benzamide 
• 117838-15-0 N-benzyl-2-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)aniline 
• 117838-07-0 4-Nitro-benzoic acid N'-(2-benzylamino-benzoyl)-hydrazide 
• 855245-86-2 2-(benzylamino)-N-phenylbenzamide 
• 130058-54-7 ethyl 4-hydroxy-2-oxo-1-(phenylmethyl)-1,2-dihydro-3-quinolinecarboxylate 
• 6622-55-5 N-benzylanthranilic acid 

Relevant academic research and scientific papers

Synthesis of Ring-Fused, N-Substituted 4-Quinolinones Using p Ka-Guided, Base-Promoted Annulations with Isatoic Anhydrides: Total Synthesis of Penicinotam

An anionic annulation strategy employing isatoic anhydrides and a wide assortment of enolizable partners was developed to afford over 80 novel ring-fused, N-substituted 4-quinolinones, an underrepresented privileged template. Multiple factors governing the efficiency of the transformation were determined, resulting in a reliable and tunable synthetic platform applicable for a broad range of substrates with variable deprotonation susceptibility, such as tetramic and tetronic acids, cyclic 1,3-diketones, and cycloalkanones. Application to the synthesis of bioactive, pyrrolizine-fused 4-quinolinone, penicinotam 3, resulted in the most brief and highest yielding total synthesis of the alkaloid in three steps and a 36% overall yield.

Unsymmetrically substituted dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A convenient scaffold for bioactive molecule design

A novel approach for the synthesis of unsymmetrically substituted dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones has been developed. This facile three-step method uses variously substituted 1H-benzo[d][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into N-alkyl-, N-acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[b,f][1,5]diazocine(5H,11H)6,12-dione framework could serve as a privileged structure for the drug design and development.

Synthesis and antibiofilm evaluation of 3-hydroxy-2,3-dihydroquinazolin-4(1H)-one derivatives against opportunistic pathogen Acinetobacter baumannii

The emergence of multidrug resistant microorganisms has triggered the impending need for new aitimicrobial strategies. The antivirulence strategy with the benefite of alleviating the drug resistance becomes the focus of research. In this study, 22 quorum sensing inhibitors were synthesized by mimicking the structure of autoinducer and acinetobactin and up to 34% biofilm inhibition was observed with 5u. The biofilm inhibition effect was further demonstrated with extracellular polysaccharides inhibition and synergism with Gentamycin sulphate.

Palladium-Catalyzed Multistep Tandem Carbonylation/N-Dealkylation/Carbonylation Reaction: Access to Isatoic Anhydrides

A novel and efficient synthesis of isatoic anhydride derivatives was developed via palladium-catalyzed multistep tandem carbonylation/N-dealkylation/carbonylation reaction with alkyl as the leaving group and tertiary anilines as nitrogen nucleophiles. This approach features good functional group compatibility and readily available starting materials. Furthermore, it provided a convenient approach for the synthesis of biologically and medicinally useful evodiamine.

One-Pot Total Synthesis of Evodiamine and Its Analogues through a Continuous Biscyclization Reaction

The one-pot total synthesis of evodiamine and its analogues is achieved using a three-component reaction. Through continuous biscyclization, various readily available substrates with good functional group tolerance were easily incorporated into biologically active quinazolinocarboline backbones. The use of triethoxymethane as a cosolvent was crucial for this quick and straightforward transformation.

IMPROVED SOLUBILITY FOR TARGET COMPOUNDS

The present disclosure relates to compounds having an improved solubility thereby increasing their bioavailability, lower dosages, etc. The target compounds, may include but are not limited to, macrophage migration inhibitory factor (MIF) inhibitors, epid

Subtly Modulating Glycogen Synthase Kinase 3 β: Allosteric Inhibitor Development and Their Potential for the Treatment of Chronic Diseases

Glycogen synthase kinase 3 β (GSK-3β) is a central target in several unmet diseases. To increase the specificity of GSK-3β inhibitors in chronic treatments, we developed small molecules allowing subtle modulation of GSK-3β activity. Design synthesis, structure-Activity relationships, and binding mode of quinoline-3-carbohydrazide derivatives as allosteric modulators of GSK-3β are presented here. Furthermore, we show how allosteric binders may overcome the β-catenin side effects associated with strong GSK-3β inhibition. The therapeutic potential of some of these modulators has been tested in human samples from patients with congenital myotonic dystrophy type 1 (CDM1) and spinal muscular atrophy (SMA) patients. We found that compound 53 improves delayed myogenesis in CDM1 myoblasts, while compounds 1 and 53 have neuroprotective properties in SMA-derived cells. These findings suggest that the allosteric modulators of GSK-3β may be used for future development of drugs for DM1, SMA, and other chronic diseases where GSK-3β inhibition exhibits therapeutic effects.

Palladium-Catalyzed Cyclization Reaction of o-Iodoanilines, CO2, and CO: Access to Isatoic Anhydrides

Isatoic anhydrides, a class of valuable synthetic intermediates and RNA structure probing reagents, are usually prepared with highly toxic phosgene or stoichiometric oxidants. Herein we report a highly selective palladium-catalyzed cyclization reaction for the efficient synthesis of isatoic anhydrides from readily available o-iodoanilines, CO2, and CO. The reaction proceeds under mild conditions and is redox-neutral. Both CO2 and CO are indispensable C1 building blocks for this catalytic reaction.

Investigation into the stability and reactivity of the pentacyclic alkaloid dehydroevodiamine and the benz-analog thereof

Limited synthetic approaches to obtain the biologically active alkaloid dehydroevodiamine (DHED) are known to date. Undesired demethylation in the most widely applied route was found to be a hampering side reaction for the benz-DHED derivative leading to a quinazolinone, which represents a benz-rutaecarpine derivative. For rutaecarpine, a related plant alkaloid, many different synthetic approaches have been described. Alternative reaction procedures to obtain DHED such as methylation of rutaecarpine and oxidation of evodiamine were investigated to make DHED more easily accessible and the latter method proved to be the most successful one. Furthermore, the remarkable equilibrium between the ring closed quinazolinium and the ring open form of the compounds was systematically investigated by UV-vis measurements. The ring open form and the quinazolinium salt, form the same species when incubated in buffer solution for 24 h. A better soluble form, i.e., 'hydroxyevodiamine', seems to represent the biologically active form that has not yet been described.

Synthesis, regioselectivity, and DFT analysis of new antioxidant pyrazolo[4,3-c]quinoline-3,4-diones

The condensation of hydrazine, N-methylhydrazine, and N-phenylhydrazine with ethyl 4-chloro-2-oxo- 1,2-dihydroquinoline-3-carboxylate derivatives has been investigated. As a result, 12 new antioxidant pyrazolo[4,3- c]quinolin-3,4-diones were obtained with good to high yields. When two cross-products could be possible, only one isomer bearing the methyl or the phenyl group at the N1 position is isolated and unequivocally characterized using 1D and 2D NMR techniques, FT-IR, and combustion analyses. DFT analysis of the reaction mechanism was carried out in the Pearson’s hard soft acid base framework, confirming the assigned structure to the observed pyrazolo[4,3-c]quinolin-3,4-diones. These calculations indicate a favored kinetic control for the synthesized pyrazolo[4,3- c]quinolin-3,4-diones compared to its possible regioisomer.