19063-58-2

Usage

Uses

Used in Pharmaceutical Industry:
7-NITROCOUMARIN is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a promising candidate for the development of new drugs with potential therapeutic applications.
Used in Antimicrobial Applications:
7-NITROCOUMARIN is used as a bacteriostatic agent for inhibiting the growth of bacteria. Its chemical properties allow it to interfere with essential bacterial processes, making it a valuable tool in the development of new antimicrobial agents to combat bacterial infections.
Used in Chemical Research:
7-NITROCOUMARIN serves as a valuable compound in chemical research, particularly in the study of coumarin derivatives and their potential applications. Its unique structure and properties make it an interesting subject for further investigation and development in the field of organic chemistry.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 35, p. 1796, 1987 DOI: 10.1248/cpb.35.1796

InChI:InChI=1/C9H5NO4/c11-9-4-2-6-1-3-7(10(12)13)5-8(6)14-9/h1-5H

Upstream product

• 2460-58-4 2-hydroxy-4-nitrobenzaldehyde 
• 108-24-7 acetic anhydride 
• 112768-00-0 (2,4-dinitro-benzylidene)-malonic acid 
• 91-66-7 N,N-diethylaniline 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 33538-99-7 2-hydroxy-5-methoxycinnamaldehyde 
• 105-53-3 diethyl malonate 
• 554-84-7 meta-nitrophenol 
• 471-25-0 Propiolic acid 
• 108530-10-5 2-oxo-2H-benzopyran-7-yl trifluoromethanesulfonate 
• 1297609-83-6 methyl (E)-3-(2-methoxy-4-nitrophenyl)acrylate 
• 5458-84-4 2-iodo-5-nitroanisole 
• 1357078-03-5 coumarin-7-boronic acid 
• 528-75-6 2,4-dinitrobenzaldehyde 

Downstream Products

• 57597-32-7 7-(benzylamino)-2H-chromen-2-one 
• 19063-57-1 7-aminocoumarin 

Relevant academic research and scientific papers

Water soluble and fluorescent copolymers as highly sensitive and selective fluorescent chemosensors for the detection of cyanide anions in biological media

We report a simple colorimetric method based on a water soluble polymer (WSP) for the sensitive and selective detection of cyanide in a biological solution. The WSPs were prepared from a radical polymerization of a methacrylate with a cyanide chemosensor moiety based on a coumarin-dicyano-vinyl derivative motif, and the polymer was then rendered water soluble by copolymerizing this hydrophobic monomer with other glyco-conjugated methacrylate derivatives. The lowest concentration for the quantification of cyanide ions was 0.05 μM, and the polymer exhibited nearly no calorimetric response to the presence of other common anions. Therefore, the chemical incorporation of some carbohydrates, as lactose or its usual monosaccharide moieties (glucose, lactose), represents a new method for the implementation of polymers for the detection of cyanide anions in water, exhibiting both good selectivity and efficiency. The Royal Society of Chemistry 2013.

Modular Synthetic Approach to Silicon-Rhodamine Homologues and Analogues via Bis-aryllanthanum Reagents

A modular synthetic approach toward diverse analogues of the far-red fluorophore silicon-rhodamine (SiR), based on a regioselective double nucleophilic addition of aryllanthanum reagents to esters, anhydrides, and lactones, is proposed. The reaction has improved functional group tolerance and represents a unified strategy toward cell-permeant, spontaneously blinking, and photoactivatable SiR fluorescent labels. In tandem with Pd-catalyzed hydroxy- or aminocarbonylation, it serves a streamlined synthetic pathway to a series of validated live-cell-compatible fluorescent dyes.

Nitroxyl (HNO) reacts with molecular oxygen and forms peroxynitrite at physiological ph: Biological implications

Nitroxyl (HNO), the protonated one-electron reduction product of NO, remains an enigmatic reactive nitrogen species. Its chemical reactivity and biological activity are still not completely understood. HNO donors show biological effects different from NO donors. Although HNO reactivity with molecular oxygen is described in the literature, the product of this reaction has not yet been unambiguously identified. Here we report that the decomposition of HNO donors under aerobic conditions in aqueous solutions at physiological pH leads to the formation of peroxynitrite (ONOO-) as a major intermediate. We have specifically detected and quantified ONOO- with the aid of boronate probes, e.g. coumarin-7-boronic acid or 4-boronobenzyl derivative of fluorescein methyl ester. In addition to the major phenolic products, peroxynitrite-specific minor products of oxidation of boronate probes were detected under these conditions. Using the competition kinetics method and a set of HNO scavengers, the value of the second order rate constant of the HNO reaction with oxygen (k = 1.8 × 104 M-1 S-1) was determined. The rate constant (k = 2 × 104 M-1 S-1) was also determined using kinetic simulations. The kinetic parameters of the reactions of HNO with selected thiols, including cysteine, dithiothreitol, N-acetylcysteine, captopril, bovine and human serum albumins, and hydrogen sulfide, are reported. Biological and cardiovascular implications of nitroxyl reactions are discussed.

FUNCTIONALISED AND SUBSTITUTED INDOLES AS ANTI-CANCER AGENTS

The present invention relates broadly to functionalised and substituted indoles, the preparation thereof and their use in the treatment of proliferative diseases such as cancer.

Ytterbium triflate promoted coupling of phenols and propiolic acids: Synthesis of coumarins

Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols and propiolic acids used as starting materials in the presence of Yb(OTf)3 hydrate 10% mol as the catalyst.

Preparation of Amino- and Formylamino-coumarins by Selective Hydrogenation of Nitrocoumarins

Nitrocoumarins are hydrogenated to give aminocoumarins and N-formylaminocoumarins in good yields by a hydrogen transfer process in the presence of triethylamine and formic acid with a Pd-C catalyst.

CONVENIENT SYNTHESIS OF A SIMPLE COUMARIN FROM SALICYLALDEHYDE AND WITTIG REAGENT (III): SYNTHESIS OF NITROCOUMARINS

Reaction of nitrosalicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in Et2NPh, in Ph2O, and in the absence of solvent (neat) at 210-215 deg C was investigated.Reaction of 3-nitrosalicylaldehyde (1d) in Et2NPh afforded the benzoxazole (6) and the aminocoumarin (3e) along with the expected coumarin (3d).It was clarified that the origin of carbon-unit introduced for the formation of the benzoxazole ring came from the alkyl group of solvent.

Synthesis of Coumarins by Nucleophilic Denitrocyclization Reaction

2-propanedioic acids(2a-c) were denitrocyclized to coumarins (3a-c) by heating in quinoline in the presence of copper powder. 2-(4-Methoxiphenyl)-3-(2-nitrophenyl)-(Z)-2-propenoic acids (6a,b,d,e) were also similarly denitrocycli