31407-28-0

Usage

Chemical compound

2-Amino-quinoline-3-carboxylic acid amide

Upstream product

• 31407-25-7 2-aminoquinoline-3-carbonitrile 
• 529-23-7 o-aminobenzaldehyde 
• 107-91-5 cyanoacetic acid amide 
• 7152-39-8 amino-2 carboxamido-3 quinoleine N-oxyde 
• 176214-83-8 o-tosylaminobenzaldehyde morpholinal 
• 552-89-6 2-nitro-benzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 75825-37-5 2-cyano-3-(2-nitrophenyl)prop-2-enamide 

Downstream Products

• 51087-70-8 3-phenyl-2-thioxo-2,3-dihydro-1H-pyrimido[4,5-b]quinolin-4-one 
• 55149-04-7 4-oxo-3,4-dihydro-pyrimido[4,5-b]quinoline-2-carboxylic acid ethyl ester 
• 180330-54-5 water ethanol 

Relevant academic research and scientific papers

NH4Cl/Zn powder: An efficient, chemoselective reducing catalyst for the microwave-assisted synthesis of 2,3-disubstituted quinolines via tandem Knoevenagel condensation

An efficient, a hitherto unreported, sustainable, and environmentally friendly microwave-assisted synthesis of 2,3-disubstituted quinolines by reductive cyclization of 2-nitrobenzaldehydes and various active methylene compounds via tandem Knoevenagel condensation promoted by an efficient eco-friendly, chemoselective reducing catalyst ammonium chloride (NH4Cl) and zinc powder was developed. This present methodology is a mild, green, efficient, and environmentally benign process as it eliminates the harsh reaction conditions, non-volatile solvents, relatively expensive reagents, high catalyst loading, and also provides a number of other benefits like fast synthesis, simple reaction set-up, and good to the excellent yield of the products.

Design, synthesis and evaluation of azaacridine derivatives as dual-target EGFR and Src kinase inhibitors for antitumor treatment

Overexpression of EGFR is often associated with advanced stage disease and poor prognosis. In certain cancers, Src works synergistically with EGFR to promote proliferation, survival, invasion and metastasis. Development of dual-target drugs against EGFR and Src is of therapeutic advantage against these cancers. Based on molecular docking and our previous studies, we rationally designed a new series of azaacridine derivatives as potent EGFR and Src dual inhibitors. Most of the synthesized azaacridines displayed good antiproliferative activity against K562 and A549?cells. The representative compound 13b showed nM IC50 values against K562 and A549?cells, and inhibited EGFR at inhibition rate of 33.53% at 10?μM and Src at inhibition rate of 72.12% at 1?μM. Furthermore, compound 13b could inhibit the expression of EGFR, p-EGFR, Src and p-Src. Moreover, 13b efficiently inhibited the invasion of tumor cells and induced cancer cells apoptosis. Our study suggested that azaacridine scaffold can be developed as novel multi-target kinase inhibitors for cancer therapy.

Aza-acridine compound and preparation method and application thereof

The invention discloses a method for efficiently preparing an aza-acridine compound. The structural formula of the aza-acridine compound is shown as a formula I; the preparation method comprises the following steps: adding a 2-aminoquinoline-3-methanamide compound and a solvent under an air condition, and heating to reaction temperature; after the reaction is ended, separating and purifying to obtain multisubstituted acridine derivatives shown as the following formula, wherein the reaction temperature is 100 to 200DEG C, and the reaction time is 1 to 24 hours. A synthetic method of the aza-acridine compound, disclosed by the invention, has the advantages of scientificity, reasonability, simple and easily-operated synthesis process and high synthetic yield; a product is easy to purify. The invention also relates to the aza-acridine compound which can be used for inhibiting EGFR (Epidermal Growth Factor Receptor) and SrC, a preparation method of the aza-acridine compound, activity of a drug containing the aza-acridine compound and the application of the drug. The compound is shown in a formula II and can be used for preparing an EGFR and SrC activity inhibitor and a disease treatment medicine activated and mediated by the EGFR and the SrC.

Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization

A novel regioselective synthesis of 2-aminoquinolines and 2-arylquinoline-3-carbonitriles is described via copper-mediated tandem reaction. Formation of substituted quinolines involves Knoevenagel condensation of ortho-bromobenzaldehyde with active methylene nitriles followed by copper-catalyzed reductive amination and intramolecular cyclization.

Synthesis of 2-aminoquinoline-3-carboamides and pyrimido[4,5-b]quinolin-4-ones through copper-catalyzed one-pot multicomponent reactions

Pyrimido[4,5-b]quinolinones have attracted considerable interest from both chemical and medicinal scientists as these compounds display remarkable antimicrobial, anti-inflammatory, antitumor, antiallergy, analgesic, and antioxidant activities. The importance of pyrimido[4,5-b]quinolinones has stimulated enormous efforts to develop efficient methodologies for their synthesis. Herein, we disclose a novel synthetic protocol toward pyrimido[4,5-b]quinolin-4-ones through Cu(OAc)2-catalyzed one-pot four-component reactions of 2-bromobenzaldehydes, aqueous ammonia, cyanoacetamides and aldehydes. The synthetic procedure combines amination/condensation/cyclization/dehydrogenation reactions in one pot, allowing synthesis of complex compounds in a simple and practical manner. Compared with literature procedures, the synthetic strategies developed herein showed advantages such as readily available and economically sustainable starting materials, structural diversity of products, good functional group tolerance, and a remarkably simple operation process.

A new modification of the Friedlaender synthesis. A simple route to 2-aminoquinoline-3-carboxylic acid and its derivatives

A new version of the Friedlaender synthesis of 2-aminoquinoline-3- carboxylic acid and its derivatives from stable 2-tosylaminobenzaldehyde or its morpholinal was proposed.

KINESIN INHIBITORS

This invention relates to the compounds of formula (I) shown below. Each variable in formula (I) is defined in the specification. These compounds can be used to treat a kinesin Eg5 protein-mediated disorder.

Evolution of the thienopyridine class of inhibitors of IκB kinase-β: Part I: Hit-to-lead strategies

High-throughput screening is routinely employed as a method for the identification of novel hit structures. Large numbers of active compounds are typically procured in this way and must undergo a rigorous validation process. This process is described in detail for a collection of screening hits identified as inhibitors of IκB kinase-β (IKKβ), a key regulatory enzyme in the nuclear factor-κB (NF-κB) pathway. From these studies, a promising hit series was selected. Subsequent lead generation activities included the development of a pharmacophore hypothesis and structure-activity relationship (SAR) for the hit series. This led to the exploration of related scaffolds offering additional opportunities, and the various structural classes were comparatively evaluated for enzyme inhibition, selectivity, and drug-like properties. A novel lead series of thienopyridines was thereby established, and this series advanced into lead optimization for further development.

Preparation electrochimique de derives de la quinoleine. II. Electroreduction d'o-nitrobenzylidenes substitues

Quinoline N-oxydes and N-hydroxyquinolones have been prepared by controlled potential electrolysis of o-nitrobenzylidenes: o-NO2-C6H4-CH=CX2, o-NO2-C6H4-CH=CRX, o-NO2-C6H4-CH=CXY (X and Y being electron withdrawing groups: CO2Et, CN, CONH2, COPh).As a gen

Structure-Activity Relationships in a Series of Novel 3,4-Dihydro-4-oxopyrimidoquinoline-2-carboxylic Acid Antiallergy Agents

A series of more than 50 new 3,4-dihydro-4-oxopyrimidoquinoline-2-carboxylic acid derivatives and related compounds with substituent variations at the 2, 3, and 5-9 positions was prepared and evaluated for antiallergy activity using the rat PCA assay.These compounds were obtained by the condensation of the appropriately substituted 2-aminoquinoline-3-carboxamides with dialkyl oxalates, followed by further chemical transformations.More than two-thirds of the compounds prepared exhibited intravenous activity ranging from 1 to 400 times disodium cromoglycate (DSCG).Structure-activity data suggest that the presence of a carboxylic acid moiety at the 2 position affords optimal potency and that esters are preferred for good oral absorption.Best oral activity, with ED50 values ranging from 0.3 to 3.0 mg/kg, was displayed by ethyl esters with methoxy and/or ethoxy groups at the 7 and 8 positions.