212322-17-3

Upstream product

• 153813-69-5 methyl 4-formyl-3-nitrobenzoate 
• 7439-89-6 iron 
• 841297-68-5 3-amino-4-dimethoxymethyl-benzoic acid methyl ester 

Downstream Products

• 841297-69-6 2-phenylquinoline-7-carboxylic acid 
• 953039-79-7 methyl 2-chloroquinazoline-7-carboxylate 
• 1315578-08-5 methyl 2-phenylquinazoline-7-carboxylate 
• 1309581-11-0 methyl 4-formyl-3-(2,2,2-trifluoroacetamido)benzoate 
• 1254343-16-2 (S)-methyl 7-phenyl-5,6,7,8-tetrahydroacridine-3-carboxylate 
• 953039-78-6 methyl 2-hydroxy-quinazoline-7-carboxylate 

Relevant academic research and scientific papers

The discovery of potent small molecule activators of human STING

The adaptor protein STING plays a major role in innate immune sensing of cytosolic nucleic acids, by triggering a robust interferon response. Despite the importance of this protein as a potential therapeutic target for serious unmet medical conditions inc

Repurposing an Aldolase for the Chemoenzymatic Synthesis of Substituted Quinolines

Quinoline derivatives are important natural products and pharmaceuticals, but their synthesis can be challenging due to poor yields, harsh reaction conditions, and instability of starting materials. Here we report the chemoenzymatic synthesis of quinaldic acids under mild conditions using an aldolase, trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (NahE, or HBPA). A series of 2-aminobenzaldehydes derived from reduction of the corresponding nitro analogue were reacted with pyruvate in the presence of NahE to give substituted quinolines in up to 93% isolated yield. This reaction differs from the aldol condensation catalyzed by NahE in vivo, instead resembling the heterocycle formation catalyzed by its homologue, dihydrodipicolinate synthase.

SMALL MOLECULE STING ANTAGONISTS

The present invention relates to compounds of formula (I). The compounds maybe used to antagonise the Stimulator of Interferon Genes (STING) protein and may thereby treat liver fibrosis, fatty liver disease, non-alcoholic steatohepatitis (NASH), pulmonary fibrosis, lupus, sepsis, rheumatoid arthritis (RA), type I diabetes, STING- associated vasculopathy with onset in infancy (SAVI), Aicardi-Goutieres syndrome (AGS), familial chilblain lupus (FCL), systemic lupus erythematosus (SLE), retinal vasculopathy, neuroinflammation, systemic inflammatory response syndrome, pancreatitis, cardiovascular disease, renal fibrosis, stroke and age-related macular degeneration (AMD).

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

Gold(I)-catalyzed unprecedented rearrangement reaction between 2-aminobenzaldehydes with propargyl amines: An expedient route to 3-aminoquinolines

Access to aminoquinolines: A gold(I)-catalyzed unprecedented rearrangement reaction between 2-aminobenzaldehydes with propargyl amine was studied. The study provided, for the first time, direct access to 3-aminoquinolines in one step starting from readily available starting materials (see scheme). Elegantly designed experiments were employed to unravel the mechanism of this unprecedented rearrangement, which are corroborated by DFT calculations.

One-pot friedlnder quinoline synthesis: Scope and limitations

A highly effective one-pot Friedlnder quinoline synthesis from o-nitroarylcarbaldehydes and ketones or aldehydes was developed and the scope and limitations of the method were examined. The o-nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of a catalytic amount of aqueous hydrochloric acid; the amino compounds were then condensed in situ with ketones or aldehydes to form mono- or disubstituted quinolines, respectively, in good-to-excellent yields (58-100%). Georg Thieme Verlag Stuttgart - New York.

α-amination of nitrogen heterocycles: Ring-fused aminals

Aromatic aminoaldehydes react with cyclic amines to produce ring-fused aminals under thermal conditions. This process is applied to two-step syntheses of the quinazolinone alkaloids deoxyvasicinone and rutaecarpine. Copyright

QUINAZOLINES FOR PDK1 INHIBITION

The invention provides novel quinazoline compounds that are inhibitors of PDK1. Also provided are pharmaceutical compositions including the compounds, and methods of treating proliferative diseases, such as cancers, with the compounds or compositions.

A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes

A simple and an efficient one-pot quinoline synthesis using inexpensive and readily available reagents was proposed. The solids were removed by filtration and the filtrate was treated with ketone and powdered KOH. The o-Nitroarylcarbaldehydes were reduced to aminocarbaldehydes with iron in the presence of catalytic HCl and subsequently condensed in situ with aldehydes or ketones to form mono- or di-substituted quinolines in high yields. The method can be used to prepare 2,3-disubstituted quinolines. A mixture of isomers was generated when an unsymmetrical ketone was used, which proved to be easily separable by silica gel column chromatography. The one-pot procedure is mild enough to allow a phenyl-substituted α,β-unsaturated ketone for using as a reactant under basic conditions in refluxing ethanol without significant competition from 1,4-Michael addition. The method provides efficient means to synthesize biologically active natural and unnatural quinoline-derived compounds.

BICYCLIC IMIDAZOL DERIVATIVES AGAINST FLAVIVIRIDAE

Disclosed are compounds, compositions and methods for treatingFlaviviridae family virus infections.