42373-56-8

Usage

Uses

Used in Bioconjugation and Fluorescent Labeling Studies:
4-Azidocoumarin is used as a photocrosslinker for the synthesis of fluorescent probes and in the investigation of protein-protein interactions. Its photochemical reactivity upon UV light exposure makes it a valuable tool in these research areas.
Used in Photodynamic Therapy Development:
4-Azidocoumarin has potential applications in the development of photodynamic therapy for the treatment of cancer and other diseases. Its photophysical properties allow it to be a candidate for targeted therapies that can be activated by light.
Used in Chemical Synthesis:
4-Azidocoumarin is utilized in the synthesis of various chemical compounds due to its reactive azido group, which can be used to form new chemical bonds and create a range of different molecules for various applications.

Upstream product

• 17831-88-8 4-chloro-2H-1-benzopyran-2-one 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 91-64-5 coumarin 
• 200055-89-6 4-(4-toluenesulfonyloxy)coumarin 

Downstream Products

• 53348-92-8 4-aminocoumarin 
• 59288-15-2 3-Amino-4-pyrrolidin-1-yl-chromen-2-one 
• 148389-68-8 [N-(2-oxo-2H-chromen-4-yl)imino]triphenyl phosphorane 
• 1417897-31-4 5-methyl-1-(4-nitrophenyl)-N-{[1-(2-oxo-2H-chromen-4-yl)-1H-1,2,3-triazol-4-yl]methyl}-1H-1,2,3-triazole-4-carboxamide 
• 1581774-97-1 5-thioxo-4-(triphenyl-λ⁵-phosphanylidene)-4,5-dihydrochromeno[4,3-d][1,2,3]triazepin-6(1H)-one 
• 1581774-98-2 5-thioxochromeno[4,3-d][1,2,3]triazepin-6(5H)-one 
• 1581774-95-9 4-(triphenyl-λ⁵-phosphanylidene)-1,4-dihydrochromeno[4,3-d][1,2,3]triazepine-5,6-dione 
• 1581774-94-8 3-(2-oxo-2H-chromen-4-yl)-5-(triphenyl-λ⁵-phosphanylidene)-3,5-dihydro-4H-1,2,3-triazol-4-one 
• 1581774-96-0 chromeno[4,3-d][1,2,3]triazepine-5,6-dione 
• 1581774-91-5 5-(phenylimino)chromeno[4,3-d][1,2,3]triazepin-6(5H)-one 
• 1581774-89-1 4-[5-(phenylimino)-4-(triphenyl-λ5-phosphanylidene)-4,5-dihydro-1H-1,2,3-triazol-1-yl]-2H-chromen-2-one 
• 1581774-90-4 5-(phenylimino)-4-(triphenyl-λ⁵-phosphanylidene)-4,5-dihydrochromeno[4,3-d][1,2,3]triazepine-6(1H)-one 

Relevant academic research and scientific papers

Synthesis and Evaluations of “1,4-Triazolyl Combretacoumarins” and Desmethoxy Analogs

1,4-Triazolyl combretacoumarins have been prepared by linking the trimethoxyarene unit of combretastatin A4 with coumarins, via a 1,2,3-triazole. For this, 4-azidocoumarins were accessed by a sequential two-step, one-pot reaction of 4-hydroxycoumarins with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), followed by reaction with NaN3. In the reaction with BOP, a coumarin-derived phosphonium ion intermediate seems to form, leading to an O4-(benzotriazolyl)coumarin derivative. For the CuAAC reaction of azidocoumarins with 5-ethynyl-1,2,3-trimethoxybenzene, catalytic [(MeCN)4Cu]PF6 in CH2Cl2/MeOH with 2,6-lutidine, at 50 oC, was suitable. The 4-azidocoumarins were less reactive as compared to PhN3 and the NBO coefficients of the azido groups were compared by DFT analysis. Compound solubility was a problem in biological assays. On the basis of the biological and solubility data of one 1,4-triazolyl combretacoumarin, four analogs lacking one or two methoxy groups were synthesized. Reactivity differences among the phenylacetylenes were noted and the NBO coefficients of the alkynes were compared by DFT analysis. In cytotoxicity assays, 1-phenyl-4-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole showed activity in CEM and MDA-MB-231 cell lines by apoptosis. The desmethoxy 6-bromo-4-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one also showed cytotoxicity against the two cell lines, but this did not appear to be consistent with apoptosis. The antiviral activity of the compounds was unremarkable.

Synthesis and biological evaluation of harmirins, novel harmine–coumarin hybrids as potential anticancer agents

As cancer remains one of the major health burdens worldwide, novel agents, due to the development of resistance, are needed. In this work, we designed and synthesized harmirins, which are hybrid compounds comprising harmine and coumarin scaffolds, evaluat

Coumarin spirooxazoline-containing compound as well as preparation method and application thereof

The invention provides a coumarin spirooxazoline-containing compound as well as a preparation method and application thereof. The coumarin spirooxazoline-containing compound is a coumarin spiro derivative formed by introducing an oxazoline heterocyclic ring to a C4 site of a coumarin parent nucleus. The structural formula of the compound is as described in the specification. In the structural formula, R1 is any one selected from the group consisting of hydrogen, an alkyl group, an alkoxy group, halogen, a nitro group and a hydroxyl group; and R2 is any one selected from the group consisting ofan alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aliphatic heterocycle and an aromatic heterocycle. The preparation method disclosed by the invention can be realized via a one-pot method, and product yield can reach 55-85%, so the method is economical and efficient; and the compound provided by the invention shows relatively high inhibitory activity on humangastric cancer cells MGC803.

Synthesis and anti-gastric cancer activity evaluation of novel triazole nucleobase analogues containing steroidal/coumarin/quinoline moieties

A series of novel triazole nucleobase analogues containing steroidal/coumarin/quinoline moieties have been synthesized based on copper-catalyzed azide-alkyne cycloaddition (CuAAC). The anti-cancer activity of the new triazole nucleobase analogues was stud

1,4-disubstituted 1,2,3-triazole nucleoside analogues, and preparation method and application thereof

The invention belongs to the technical field of pharmaceutical chemistry, and relates to 1,4-disubstituted 1,2,3-triazole nucleoside analogues: design, synthesis and anti-gastric cancer activity research. The purine nucleoside analogues have the following

Cu (I) Catalyzed One Pot SN-Click Reactions of Halogenated Coumarins and 1-aza-coumarins

A one pot three component, copper catalyzed azide-alkyne cycloaddition reaction has been employed for the synthesis of bis-coumarinyl triazoles (A–D) using 4-chloro, 4-bromomethyl, 3-bromoacetyl and 4-bromomethyl-1-aza-coumarins (I–IV), sodium azide, and coumarin propargyl ethers (V–IX) in moderate yields.

Highly selective and sensitive coumarin–triazole-based fluorometric ‘turn-off’ sensor for detection of Pb2+ ions

Exposure to even very low concentrations of Pb2+ is known to cause cardiovascular, neurological, developmental, and reproductive disorders, and affects children in particular more severely. Consequently, much effort has been dedicated to the de

Synthesis, Absorption, and Fluorescence Studies of Coumaryl-Labelled Amino Acids and Dipeptides Linked Via Triazole Ring

Fluorophores based on 4-triazolyl, 7-hydroxy-4-triazolylmethyl, 4-O-triazolylmethyl, and 7-O-triazolylmethyl coumaryl-tagged amino acids and dipeptides were synthesized by copper-catalyzed [3+2] cycloaddition reaction between azido- or alkynyl-functionalized coumarins with alkynyl- or azido-functionalized amino acid and dipeptides in good-to-excellent yields. Steady-state absorption and the fluorescence properties of the synthesized conjugates were studied. The chemical applicability of these amino acid and peptide-based fluorophores was successfully demonstrated by their linear elongation by further tagging them with appropriate C- or N-terminus amino acid.

Estimation of ground and excited state dipole moments of synthesized coumarin derivative [N-(2-oxo-2H-chromen-4-yl)imino]triphenyl-phosphorane

Electronic absorption and fluorescence spectra of coumarin derivative [N-(2-oxo-2H-chromen-4-yl)imino] triphenyl phosphorane have been recorded at room temperature in wide range of solvents of different polarities. The absorption maximum remains almost un

Synthesis and biological evaluation of 4-(1,2,3-triazol-1-yl)coumarin derivatives as potential antitumor agents

In this research, a series of 4-(1,2,3-triazol-1-yl)coumarin conjugates were synthesized and their anticancer activities were evaluated in vitro against three human cancer cell lines, including human breast carcinoma MCF-7 cell, colon carcinoma SW480 cell and lung carcinoma A549 cell. To increase the biological potency, structural optimization campaign was conducted focusing on the C-4 position of 1,2,3-triazole and the C-6, C-7 positions of coumarin. In addition, to further evaluate the role of 1,2,3-triazole and coumarin for antiproliferative activity, 9 compounds possessing 4-(piperazin-1-yl)coumarin framework and 3 derivatives baring quinoline core were also synthesized. By MTT assay in vitro, most of the compounds display attractive antitumor activities, especially 23. Further flow cytometry assays demonstrate that compound 23 exerts the antiproliferative role through arresting G2/M cell-cycle and inducing apoptosis.