35490-90-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-6-chlorobenzaldehyde serves as a key starting material in the organic synthesis of various pharmaceuticals. Its unique structure allows for the development of a range of medicinal compounds, making it valuable in drug discovery and production.
Used in Dye Industry:
In the dye industry, 2-Amino-6-chlorobenzaldehyde is utilized for the production of different types of dyes. Its chemical properties contribute to the creation of dyes with specific color characteristics and applications in various settings.

Upstream product

• 6575-11-7 2-amino-6-chlorobenzonitrile 
• 6361-22-4 2-chloro-6-nitrobenzaldehyde 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 387-45-1 2-chloro-6-fluorobenzaldehyde 
• 39885-08-0 (2-amino-6-chlorophenyl)methanol 

Downstream Products

• 60610-16-4 5-chloroquinazolin-2-ol 
• 1395473-86-5 (S)-5-chloro-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline 
• 445041-29-2 2,5-dichloroquinazoline 
• 1064137-50-3 2,5-dichloroquinoline-3-carbaldehyde 
• 889939-13-3 ethyl 5-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate 
• 511231-70-2 5-chloro-quinoline-2-carboxylic acid 
• 2102411-05-0 5-chloroquinoline-3-carbonitrile 
• 1194-64-5 2-chloro-6-methylbenzaldehyde 
• 60610-16-4 5-chloroquinazolin-2(1H)-one 

Relevant academic research and scientific papers

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.

IMIDAZOPIPERAZINONE INHIBITORS OF TRANSCRIPTION ACTIVATING PROTEINS

The present disclosure relates to heterocyclic compounds and methods which may be useful as inhibitors of transcription activating proteins such as CBP and P300 for the treatment or prevention of diseases such as proliferative diseases, inflammatory disorders, autoimmune diseases, and fibrotic diseases.

HETEROARYL DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL COMPOSTION FOR PREVENTING OR TREATING DISEASES ASSOCIATED WITH PI3 KINASES, CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a heteroaryl derivative or a pharmaceutically acceptable salt thereof, a preparation method therefor, and a pharmaceutical composition for preventing or treating diseases associated with PI3 kinases, containing the same as an active ingredient. The heteroaryl derivative according to the present invention has an excellent effect of selectively inhibiting PI3 kinases, thereby being useful in preventing or treating PI3 kinase diseases such as: cancers, autoimmune diseases, and respiratory diseases.

Vasicine from Adhatoda vasica as an organocatalyst for metal-free Henry reaction and reductive heterocyclization of o-nitroacylbenzenes

Vasicine, a quinazoline alkaloid, from the leaves of Adhatoda vasica, has been utilized as an efficient catalyst for metal and base free Henry reaction of various aldehydes with nitro alkanes. The method can be used in the synthesis of various β-nitro alcohols under mild reaction conditions without use of hazardous organic solvents and expensive catalysts. Vasicine is also applied successfully for one pot synthesis of 2,1-benzisoxazoles from o-nitroacylbenzenes in good yields under mild conditions.

Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes

A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

Chemoselective Oxidation of Benzyl, Amino, and Propargyl Alcohols to Aldehydes and Ketones under Mild Reaction Conditions

Catalytic oxidation reactions often suffer from drawbacks such as low yields and poor selectivity. Particularly, selective oxidation of alcohols becomes more difficult when a compound contains more than one oxidizable functional group. In order to deliver a methodology that addresses these issues, herein we report an efficient, aerobic, chemoselective and simplified approach to oxidize a broad range of benzyl and propargyl alcohols containing diverse functional groups to their corresponding aldehydes and ketones in excellent yields under mild reaction conditions. Optimal yields were obtained at room temperature using 1 mmol substrate, 10 mol% copper(I) iodide, 10 mol% 4-dimethylaminopyridine (DMAP), ands 1 mol% 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) in acetonitrile, under an oxygen balloon. The catalytic system can be applied even when sensitive and oxidizable groups such as alkynes, amines, and phenols are present; starting materials and products containing such groups were found to be stable under the developed conditions.

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

HETEROCYCLIC COMPOUNDS AND THEIR USES

Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjoegren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity. The present invention also enables methods for treating cancers that are mediated, dependent on or associated with p110δ activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo-dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia (T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.

PHARMACEUTICAL COMPOSITION AND PROCESS

There is provided a formulation comprising N-(2-chloro-6-methylbenzoyl)-4- [(2,6-dichlorobenzoyl)amino]-L-phenylalanine-2(diethylamino)ethyl ester and poloxamer 188 which is manufactured by a hot melt process.