20028-53-9

Usage

Uses

Used in Organic Synthesis:
2-Amino-5-chlorobenzaldehyde is used as a raw material in organic synthesis for the production of a wide range of chemical compounds. Its versatile structure allows for various chemical reactions, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
2-Amino-5-chlorobenzaldehyde is used as a pharmaceutical intermediate for the development of various drugs. Its unique structure and reactivity make it an essential component in the synthesis of pharmaceutical compounds, contributing to the discovery and production of new medications.

InChI:InChI=1/C7H6ClNO/c8-6-1-2-7(9)5(3-6)4-10/h1-4H,9H2

Upstream product

• 73033-58-6 5-chloro-2-nitrobenzyl alcohol 
• 635-21-2 5-chloroanthranilic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 37585-25-4 2-amino-5-chlorobenzyl alcohol 
• 106-47-8 4-chloro-aniline 
• 68-12-2 N,N-dimethyl-formamide 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 

Downstream Products

• 144155-69-1 7-chloro-3,4-dihydro-3-<4-(trifluoromethyl)phenyl>-1(2H)-acridinone 
• 1334951-08-4 5-chloro-2-(4-methoxyphenyl)-2H-indazole 
• 916664-23-8 2-azido 5-chlorobenzaldehyde 
• 916056-79-6 6-chloro-3-amino-2-(2-hydroxyisopropyl)-1-azanaphthalene 
• 17630-75-0 5-chloro-indolin-2-one 
• 59394-30-8 6-chloro-2-quinolinecarboxylic acid 
• 261521-60-2 5-chloro-2-formamidobenzaldehyde 
• 86209-35-0 6-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 

Relevant academic research and scientific papers

Rediscovered synthesis of 3-cyanoquinoline derivatives

The easy and rapid synthetic procedure for the synthesis of substituted 3-cyanoquinoline derivatives using available laboratory reagents is reported. Vilsmeier-Haack reaction is employed to the p-substituted aniline to yield formyl aniline. These on reaction with cyano ethylacetate and with malono nitrile in presence catalyst results in to 3-substituted quinolines.

Silver-Catalyzed Three-Component Coupling Reaction of Amines, 2-Isocyanobenzaldehydes, and 2,2,2-Trifluorodiazoethane and Synthesis of Trifluoromethyl-Substituted Indolo[1,2-c]quinazolines

A silver-catalyzed three-component coupling reaction of amines, 2-isocyanobenzaldehydes, and 2,2,2-trifluorodiazoethane has been developed. This reaction provides an efficient method for the construction of CF3-containing dihydroquinazolines. On the basis of this reaction, using trifluorodiazoethyl-substituted dihydroquinazolines as synthons, trifluoromethyl-substituted indolo[1,2-c]quinazolines were prepared in high yields via a TBHP/KI-mediated sequential intramolecular cyclization and aromatization process. (Figure presented.).

PPTS-Catalyzed Bicyclization Reaction of 2-Isocyanobenzaldehydes with Various Amines: Synthesis of Diverse Fused Quinazolines

A PPTS (pyridinium p-toluenesulfonate)-catalyzed bicyclization reaction of 2-isocyanobenzaldehydes as 1,5-dielectrophiles with various amines has been developed. The reaction not only provides a simple and efficient strategy for the assembly of structurally diverse fused quinazoline derivatives from readily available substrates under metal-free and mild conditions in a single step with only water and hydrogen as the by-products, but also opens the way to the application of o-formyl arylisocyanides in the synthesis of nitrogen-containing heterocycles. (Figure presented.).

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.

Identification of Inhibitors of Cholesterol Transport Proteins Through the Synthesis of a Diverse, Sterol-Inspired Compound Collection

Cholesterol transport proteins regulate a vast array of cellular processes including lipid metabolism, vesicular and non-vesicular trafficking, organelle contact sites, and autophagy. Despite their undoubted importance, the identification of selective modulators of this class of proteins has been challenging due to the structural similarities in the cholesterol-binding site. Herein we report a general strategy for the identification of selective inhibitors of cholesterol transport proteins via the synthesis of a diverse sterol-inspired compound collection. Fusion of a primary sterol fragment to an array of secondary privileged scaffolds led to the identification of potent and selective inhibitors of the cholesterol transport protein Aster-C, which displayed a surprising preference for the unnatural-sterol AB-ring stereochemistry and new inhibitors of Aster-A. We propose that this strategy can and should be applied to any therapeutically relevant sterol-binding protein.

ALDEHYDE CONJUGATES AND USES THEREOF

The present invention provides compounds and methods of use thereof for the treatment, prevention, and/or reduction of a risk of a disease, disorder, or condition in which aldehyde toxicity is implicated in the pathogenesis, including ocular disorders, skin disorders, conditions associated with injurious effects from blister agents, and autoimmune, inflammatory, neurological and cardiovascular diseases by the use of a primary amine to scavenge toxic aldehydes, such as MDA and HNE.

Design, synthesis, and anticancer evaluation of novel quinoline derivatives of ursolic acid with hydrazide, oxadiazole, and thiadiazole moieties as potent MEK inhibitors

In this article, a series of novel quinoline derivatives of ursolic acid (UA) bearing hydrazide, oxadiazole, or thiadiazole moieties were designed, synthesised, and screened for their in vitro antiproliferative activities against three cancer cell lines (MDA-MB-231, HeLa, and SMMC-7721). A number of compounds showed significant activity against at least one cell line. Among them, compound 4d exhibited the most potent activity against three cancer cell lines with IC50 values of 0.12 ± 0.01, 0.08 ± 0.01, and 0.34 ± 0.03 μM, respectively. In particular, compound 4d could induce the apoptosis of HeLa cells, arrest cell cycle at the G0/G1 phase, elevate intracellular reactive oxygen species level, and decrease mitochondrial membrane potential. In addition, compound 4d could significantly inhibit MEK1 kinase activity and impede Ras/Raf/MEK/ERK transduction pathway. Therefore, compound 4d may be a potential anticancer agent and a promising lead worthy of further investigation.

Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation

Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2-aminobenzaldehydes and 2-aminoaryl ketones under solvent-free conditions, employing 1,3-bis(carboxymethyl)-imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Additionally, 3-acetylquinolines have been transformed, under solvent-free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E-factors are in the range of 14–23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described.

ALDEHYDE TRAPPING COMPOUNDS AND METHODS OF USE THEREOF

The present invention provides compounds and methods for the treatment, prevention, and/or reduction of a risk of a disease, disorder, or condition in which aldehyde toxicity is implicated in the pathogenesis, including ocular disorders, skin disorders, conditions associated with injurious effects from blister agents, and autoimmune, inflammatory, neurological and cardiovascular diseases by the use of a primary amine to scavenge toxic aldehydes, such as MDA and HNE.

Enantioselective Organocatalytic Intramolecular Aza-Diels–Alder Reaction

A highly efficient catalytic enantioselective intramolecular Povarov reaction was developed with primary anilines as 2-azadiene precursors. A wide variety of angularly fused azacycles were obtained without column chromatography in high to excellent yields and with excellent diastereo- and enantioselectivity (d.r.>99:1 and up to e.r. 99:1). Furthermore, the catalyst loading could be lowered to 1 mol %, and the obtained azacycles could be used as key intermediates for further transformations to generate additional molecular diversity.