1635-31-0

Usage

Uses

Used in Chemical Synthesis:
3-Aminocoumarin is used as a starting reagent for the synthesis of 1,2,3,4-tetrahydropyrido[2,3-c]coumarins, which are important intermediates in the development of various pharmaceutical compounds.
Used in Coordination Chemistry:
3-Aminocoumarin serves as a ligand for the synthesis of metal complexes, specifically with Cr(III), Ni(II), and Cu(II). These complexes have potential applications in various fields, including catalysis and material science.
Used in Medicinal Chemistry:
3-Aminocoumarin is utilized in the synthesis of new 3-(heteroaryl)aminocoumarin derivatives through an optimized Buchwald-Hartwig amination reaction. These derivatives may exhibit biological activities and could be further explored for their potential use in the development of new drugs and therapeutic agents.

InChI:InChI=1/C9H7NO2/c10-7-5-6-3-1-2-4-8(6)12-9(7)11/h1-5H,10H2

Upstream product

• 779-30-6 3-acetamidocoumarin 
• 66949-73-3 ethyl N-salicylideneglycinate 
• 7647-01-0 hydrogenchloride 
• 939-18-4 3-bromo-2H-chromen-2-one 
• 28448-04-6 3-nitrocoumarin 
• 1236145-31-5 1-(2-imino-2H-chromen-3-yl)pyridinium chloride 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 90-02-8 salicylaldehyde 
• 543-24-8 N-acetylglycine 
• 922167-67-7 C₉H₁₁NO₂ 
• 188815-41-0 7-chloro-5-bromo coumarin 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 939-19-5 3-Hydroxy-cumarin 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 130090-76-5 N-(2-oxo-2H-1-benzopyran-3-yl)phthalamic acid 
• 80613-79-2 3-(N-tosyl-L-Ala)aminocoumarin 
• 80657-53-0 3-(N-Tosyl-DL-Ala)aminocoumarin 
• 134268-98-7 Boc-Phe-NH-c 
• 80613-82-7 3-(N-tosyl-DL-Ser)aminocoumarin 
• 80613-81-6 3-(N-tosyl-DL-Val)aminocoumarin 
• 80613-80-5 N-(2-Oxo-2H-chromen-3-yl)-3-(toluene-4-sulfonylamino)-propionamide 
• 76461-89-7 3-N-cinnamoylaminocoumarin 
• 144616-80-8 3-{[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-amino}-chromen-2-one 
• 144616-81-9 3-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-chromen-2-one 
• 65612-49-9 1-(2-Oxo-2H-chromen-3-yl)-3-p-tolyl-thiourea 
• 144616-86-4 3-{[1-(2,6-Dichloro-phenyl)-meth-(E)-ylidene]-amino}-chromen-2-one 
• 144616-90-0 3-{[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-chromen-2-one 
• 144616-91-1 N-(4-{[(E)-2-Oxo-2H-chromen-3-ylimino]-methyl}-phenyl)-acetamide 

Relevant academic research and scientific papers

Synthesis of 3-aminocoumarin-N-benzylpyridinium conjugates with nanomolar inhibitory activity against acetylcholinesterase

A series of 3-amino-6,7-dimethoxycoumarins conjugated with the N-benzylpyridinium moiety through an amide-bond linkage was synthesized and evaluated for their acetylcholinesterase inhibitory activity. A number of the benzylpyridinium derivatives exhibited potent activities with inhibitory concentration (IC50) values in the nanomolar concentration range. Among them, the 2,3-difluo-robenzylpyridinium-containing compound was the most potent inhibitor with an IC50 value of 1.53 ± 0.01 nM. Docking studies revealed that the synthesized compounds inhibit the target enzyme by a dual binding site mechanism whereby the coumarin portion binds with the peripheral anionic site while the N-benzylpyridinium residue binds with the catalytic anionic site of the enzyme.

Synthesis of substituted 3-aminocoumarins from ethyl N-2- hydroxyarylideneglycinates

3-Aminocoumarin and its derivatives are prepared by a thermal (150- 170°C) conversion reaction on the corresponding ethyl N-2- hydroxyarylideneglycinates,[2-HOC6H3(X)CH=NCH2CO2C2Hs; X = H, 5-Br, 5- OH, 5-NO2, 3-OMe, 4-OMe, and 5,6-benzo], which are synthesized by condensing ethyl glycinate hydrochloride with substituted salicylaldehyde.

Tyrosine-like condensed derivatives as tyrosinase inhibitors

Objectives We report the pharmacological evaluation of a new series of 3-aminocoumarins differently substituted with hydroxyl groups, which have been synthesized because they include in their structures the tyrosine fragment (tyrosine-like compounds), with the aim of discovering structural features necessary for tyrosinase inhibitory activity. Methods The synthesized compounds 4 and 7-9 were evaluated in vitro as mushroom tyrosinase inhibitors. Key findings Two of the described compounds showed lower IC50 (concentration giving 50% inhibition of tyrosinase activity) than umbelliferone, used as a reference compound. Conclusions Compound 7 (IC50 = 53 μm) was the best tyrosinase inhibitor of this small series, having an IC50 value 10-fold lower than umbelliferone. Compound 7 (3-amino-7-hydroxycoumarin) had amino and hydroxyl groups precisely mimicking the same positions that both groups occupy on the tyrosine molecule. 2012 The Authors. JPP

Design, synthesis and biological evaluation of selective hybrid coumarin-thiazolidinedione aldose reductase-II inhibitors as potential antidiabetics

Thiazolidinediones (TZD), benzopyrans are the proven scaffolds for inhibiting Aldose reductase (ALR2) activity and their structural confluence with the retention of necessary fragments helped in designing a series of hybrid compounds 2-(5-cycloalkylidene-2,4-dioxothiazolidin-3-yl)-N-(2-oxo-2H-chromen-3-yl)acetamide (10a-n) for better ALR2 inhibition. The compounds were synthesized by treating substituted 3-(N-bromoacetyl amino)coumarins (9a-d) with potassium salt of 5-cyclo alkylidene-1,3-thiazolidine-2,4-diones (4a-d). The inhibition activity against ALR2 with IC50 values range from 0.012 ± 0.001 to 0.056 ± 0.007 μM. N-[(6-Bromo-3-coumarinyl)-2-(5-cyclopentylidene-2,4-dioxothiazolidin-3-yl)] acetamide (10c) with cyclopentylidene group on one end and the 6-bromo group on the other end showed better inhibitory property (IC50 = 0.012 μM) and selectivity index (324.166) against the ALR2, a forty fold superiority over sorbinil, a better molecule over epalrestat and rest of the analogues exhibited a far superior response over sorbinil and slightly better as compared with epalrestat. It was further confirmed by the insilico studies that compound 10c showed best inhibition activity among the synthesized compounds with a high selectivity index against the ALR2. In invivo experiments, supplementation of compound 10c to STZ induced rats delayed the progression of cataract in a dose-dependent manner warranting its further development as a potential agent to treat the diabetic secondary complications especially cataract.

An efficient and facile synthesis of substituted 3-aminocoumarins under mw irradiation in dry media

A variety of 3-aminocoumarins were prepared by reaction of salicylaldehyde derivatives with benzoylglycine catalyzed by piperidine under microwave irradiation (MWI) and subsequent acid hydrolysis. The structure of products was proven by elemental analysis, IR, NMR and Mass spectra. These investigations will contribute to development of environmentally friendly and inexpensive processes in organic synthesis.

A highly selective fluorescent probe for detection of Cd2+ and HSO3- based on photochromic diarylethene with a triazole-bridged coumarin-quinoline group

A novel photochromic diarylethene containing a quinoline-linked 3-aminocoumarin Schiff base unit (1O) was synthesized and used for the selective detection of Cd2+ and HSO3-. The synthesized probe exhibited a straightforward response for the selective detection of Cd2+. Its fluorescence emission red-shifted ～126 nm and was enhanced 24.9 fold in the presence of Cd2+. Meanwhile, the fluorescence color of 1O changed from dark cyan to golden yellow. The binding stoichiometry between 1O and Cd2+ was determined to be 1:1. A molecular logic circuit with three inputs and one output was successfully constructed with its light and metal-responsive behaviors. In addition, 1O was able to selectively recognize HSO3- with a 135-fold enhanced fluorescence emission and a notable fluorescence color change from dark cyan to bright cyan. The 1H NMR and mass spectrometry analyses suggest that the HSO3- sensing of 1O is based on the hydrolysis of the Schiff base group of 1O.

Design and synthesis of aminocoumarin derivatives as DPP-IV inhibitors and anticancer agents

DPP-IV “a moonlighting protein” has immerged as promising pathway to control Type 2 diabetes as well as found to play key role in earlier stages of cancer. Here we have reported design, synthesis and applications of aminocoumarin derivatives as DPP-IV inhibitors. Compounds have been synthesized and studied for their DPP-IV inhibition activity. Three compounds have shown moderate inhibition at 100 μM concentration. All compounds were also screened for their anticancer activity against A549 (Lung cancer cell line), MCF-7 (Breast cancer cell line) using MTT assay. One of the compounds has shown very good anticancer activity with IC50 value 24 ± 0.1 nM against A549 cell line.

Development of surface immobilized 3-azidocoumarin-based fluorogenic probe via strain promoted click chemistry

A new class of imaging probe, a fluorogenic version of 1, 3-dipolar cycloaddition of azides and alkynes has been developed. 3-azidocoumarin scaffolds were selectively immobilized on the DBCO modified bead surface via SPAAC and provide direct and strong fluorescence in fluorescence microscopy. This developed click-on beads could be applied to label various biomolecules, such as nucleic acids, proteins and other molecules. To this end, 5′(7-hydroxy 3-azido coumarin) labelled DNA primer also displayed strong fluorescence upon successful immobilization on the bead surface.

Design, synthesis and biological evaluation of amino organophosphorus imidazoles as a new type of potential antimicrobial agents

A series of amino organophosphorus imidazoles were designed and synthesized as a novel structural type of antimicrobial agents. Bioactive evaluation in vitro showed that compound 3f exhibited equipotent or superior anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) and anti-S. cerevisiae efficiencies (minimal inhibitory concentration (MIC)=2 μg/mL) to clinical drugs, and the combinations with antibacterial or antifungal drugs enhanced the antimicrobial efficiency. Highly active molecule 3f showed low propensity for bacteria to develop resistance, and the preliminary action mechanism studies demonstrated that 3f was membrane-active, but had no significant intercalation towards MRSA DNA. The computational study on 3f reasonably explained its high antimicrobial activity. Experimental data revealed that ground-state 3f-HSA complexes were formed mainly through hydrophobic interactions and hydrogen bonds with a spontaneous process, and the non-radioactive energy transfer from HSA to 3f occurred beyond F?rster resonance energy transfer theory. The participation of metal ions in 3f-HSA supramolucular system could increase the concentration of free compound 3f, and shorten its storage time and half-life in the blood to improve the maximum antimicrobial efficacy.

Synthesis and cytotoxicity study of novel 3-(triazolyl)coumarins based fluorescent scaffolds

Recently a choice of fluorescent bioimaging probes have been developed as medical diagnostic tools. Herein, we have introduced a series of coumarin-based target specific probes for cancer theranostic application which play a dual role in the field of both diagnosis and therapy. A fluorogenic version of 1,3-dipolar cycloaddition between azides and alkynes (DBCO) has been introduced to develop the triazolylcoumarin based fluorescent scaffolds. These scaffolds were screened for their anticancer activity against breast cancer (MCF7) and human epitheloid cervix carcinoma (HeLa) cell line. It was established that triazolylcoumarins (5c and 5d) are having electronegative substitution in the benzene ring displayed most effective anticancer profile in both the cell lines. Compounds 5a and 5d exhibited maximum quantum yield and strong cellular uptake in the MCF-7 cell line.