69321-36-4

Usage

Uses

Used in Pharmaceutical Industry:
(4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE is used as a potential anti-inflammatory agent for its ability to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
(4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE is used as a potential anti-cancer agent for its ability to inhibit the growth of various cancer cell lines, making it a promising candidate for further drug development.
(4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE is used as a potential antimicrobial agent for its ability to inhibit the growth of bacteria, offering a potential solution for bacterial infections.
(4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE is used as a potential antiviral agent for its ability to inhibit viral replication, providing a potential treatment for viral infections.

InChI:InChI=1/C12H12N2O4/c1-7-4-12(16)18-10-5-8(2-3-9(7)10)17-6-11(15)14-13/h2-5H,6,13H2,1H3,(H,14,15)

Upstream product

• 89316-64-3 methyl 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetate 
• 5614-82-4 ethyl 2-(4-methyl-2-oxo-2-coumarin-7-yloxy)acetate 
• 108-46-3 recorcinol 
• 181482-48-4 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetamide 
• 64700-15-8 7-(carboxymethoxy)-4-methylcoumarin 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 

Downstream Products

• 69560-83-4 7-[4-(dimethylamino-methyl)-5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethoxy]-4-methyl-chromen-2-one 
• 69560-82-3 7-[4-(diethylamino-methyl)-5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethoxy]-4-methyl-chromen-2-one 
• 69560-84-5 4-methyl-7-(4-pyrrolidin-1-ylmethyl-5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethoxy)-chromen-2-one 
• 69560-79-8 4-methyl-7-(4-piperidin-1-ylmethyl-5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethoxy)-chromen-2-one 
• 69560-81-2 4-methyl-7-(4-morpholin-4-ylmethyl-5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethoxy)-chromen-2-one 
• 69560-85-6 4-methyl-7-[4-(4-methyl-piperazin-1-ylmethyl)-5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethoxy]-chromen-2-one 
• 69560-86-7 4-methyl-7-[4-(4-phenyl-piperazin-1-ylmethyl)-5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethoxy]-chromen-2-one 
• 69560-80-1 4-methyl-7-[5-thioxo-4-(4-p-tolyl-piperazin-1-ylmethyl)-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethoxy]-chromen-2-one 
• 72000-23-8 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-N'-(4-hydroxybenzylidene)acetohydrazide 
• 1159773-33-7 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-N'-(3-chlorobenzylidene)acetohydrazide 
• 72000-25-0 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-N'-(3-phenylallylidene)acetohydrazide 
• 1373762-77-6 7-({5-[(3,5-bis-triflouromethylphenyl)-2-oxoethylsulfanyl]-1,3,4-oxadiazol-2-yl}methoxy)-4-methylchromen-2-one 
• 1373762-78-7 7-({5-[(3-fluoro-4-methoxyphenyl)-2-oxoethylsulfanyl]-1,3,4-oxadiazol-2-yl}methoxy)-4-methylchromen-2-one 
• 1373762-71-0 7-((5-((2-(4-chlorophenyl)-2-oxoethyl)thio)-1,3,4-oxadiazol-2-yl)methoxy)-4-methyl-2H-chromen-2-one 

Relevant academic research and scientific papers

Antioxidant activities of 4-methylumbelliferone derivatives

The synthesis of derivatives of 4-Methylumbelliferone (4-MUs), which are structurally interesting antioxidants, was performed in this study. The modification of 4-Methylumbelliferone (4-MU) by different reaction steps was performed to yield the target compounds, the 4-MUs. The 4-MUs were characterized by different spectroscopic techniques (Fourier transform infrared; FT-IR and Nuclear magnetic resonance; NMR) and micro-elemental analysis (CHNS). The in vitro antioxidant activity of the 4-MUs was evaluated in terms of their free radical scavenging activities against 2,2-diphenyl-1-picrylhydrazyl (DPPH), Nitric oxide radical scavenging activity assay, chelating activity and their (FRAP) ferric-reducing antioxidant power, which were compared with a standard antioxidant. Our results reveal that the 4-MUs exhibit excellent radical scavenging activities. The antioxidant mechanisms of the 4-MUs were also studied. Density Function Theory (DFT)-based quantum chemical studies were performed with the basis set at 3-21G. Molecular models of the synthesized compounds were studied to understand the antioxidant activity. The electron levels, namely HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital), for these synthesized antioxidants were also studied.

Hydrogen peroxide scavenging activity of novel coumarins synthesized using different approaches

New derivatives of 7-hydroxy-4-methylcoumarin were synthesized using a chemical method and a microwave-assisted method to compare the feasibility, reaction times, and yields of the product. The newly synthesized coumarins were characterized by different spectroscopic techniques (FT-IR and NMR) and micro-elemental analysis (CHNS). In vitro antioxidant activities of these compounds were evaluated against hydrogen peroxide and were compared with standard natural antioxidant, vitamin C. Our results reveal that these compounds exhibit excellent radical scavenging activities.

Synthesis and Antibacterial Activity of Analogs of 5-Arylidene-3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazoli-din-4-one

In an effort to develop new antimicrobial agents, 3-(4-methylcoumarin-7- yloxyacetylamino)-2-thioxo-1,3-thiazolidin-4-one (4) was synthesized by reaction of thiocarbonylbisthioglycolic acid with ethyl (4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3), which was prepared in turn from 7-hydroxy-4-methylcoumarin (1). The condensation of compound 4 with different aromatic aldehydes afforded a series of 5-(arylidene)-3-(4-methylcoumarin-7-yloxyacetyl-amino)-2-thioxo-1,3-thiozolidin-4-one analogs 5a-h. The structures of these synthetic compounds were elucidated on the basis of IR, 1H-NMR and 13C-NMR spectral data and ESI-MS spectrometric analysis. Compounds 5a-h were examined for their antibacterial activity against several strains of Gram-positive and Gram-negative bacteria.

N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides

A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.

Design synthesis and anti-proliferative activity of some new coumarin substituted hydrazide–hydrazone derivatives

Abstract: A series of 21 coumarin hydrazide–hydrazone derivatives were designed, synthesized and evaluated potential cytotoxicity effects at 25 μg/mL for 48 h against liver cancer (HepG2) cell line in vitro. Then, seven out of 21 compounds with % cell via

Identification of a Novel Oxadiazole Inhibitor of Mammalian Target of Rapamycin

We performed a biochemical screen against mTOR using in-house small molecule library. Two novel, structurally distinct hits were identified. Among them, a novel oxadiazole scaffold compound (2) suppressed the phosphorylation of both S6K1 and Akt1 in HeLa cells. Docking study suggested that 2 is ATP-competitive and shows a pi-pi interaction with Trp2239 and hydrogen bonds with Trp2239 and Thr2245. Through derivatization, a slightly more potent analogue (2a) was identified with IC50 of 9.6 μM. Our study provides a starting point for discovery of novel potent mTOR inhibitors.

Synthesis and biological evaluation of coumarin-1,3,4-oxadiazole hybrids as selective carbonic anhydrase IX and XII inhibitors

With an aim to develop novel heterocyclic hybrids as potent anticancer agents, we synthesized a series of coumarin-1,3,4-oxadiazole hybrids (7a-t) and evaluated for their inhibitory activity against the four physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms CA I, CA II, CA IX and CA XII. The CA inhibition results clearly indicated that the coumarin-1,3,4-oxadiazole derivatives (7a-t) exhibited selective inhibition of the tumor associated isoforms, CA IX and CA XII over CA I and II isoforms. Among all, compound 7b, exhibited significant inhibition in lower micromolar potency against hCA XII, with a Ki of 0.16 μM and compound 7n, exhibited significant inhibition in lower micromolar potency against hCA IX, with a Ki of 2.34 μM respectively. Therefore, compound 7b and 7n could be the potential leads for development of selective anticancer agents by exhibiting a novel mechanism of action through hCA IX and XII inhibition.

Fluorescence chemosensor containing 4-methyl-7-coumarinyloxy, acetylhydrazono and N-phenylaza-15-crown-5 moieties for K+ and Ba2+ ions

A new aza-15-crown-5 derivative 1 bearing coumarin and hydrazone moieties was synthesized and characterized. The fluorescent sensing behavior and selectivity of 1 toward different metal ions in ethanol were investigated. There are 4-fold and 2-fold fluore

Biological study on novel coumarinyl 1,3,4-oxadiazoles

Coumarinyl 1,3,4-oxadiazoles were synthesized from Schiff bases and acetic anhydride. All compounds were characterized by melting points and their structures confirmed by mass and 1 H and 13 C NMR spectrometry. These novel coumarinyl

Novel hybrid-pyrrole derivatives: Their synthesis, antitubercular evaluation and docking studies

Using novel hybrid molecules for the treatment of tuberculosis is one of the latest approaches. Keeping this concept in mind, thirty two hybrid compounds were synthesized, with pyrrole as one of the moieties, clubbed to coumarin, ibuprofen and isoniazid. The compounds were evaluated against Mycobacterium tuberculosis H37Rv strain. Compounds 7e and 8e exhibited MIC of 3.7 and 5.10 μg mL-1 and growth inhibition of 95% and 92%, respectively. These compounds were also active against single drug resistant bacterial strains. The compounds were devoid of cytotoxicity when tested against Vero African green monkey kidney cell line. Docking study was carried out on enoyl acyl carrier protein enzyme to provide some understanding into the mechanism of action of these compounds.