69321-36-4

Basic information

• Product Name: (4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE
• Synonyms: 2-[(4-Methyl-2-oxo-2H-chromen-7-yl)oxy]-acetohydrazide;2-(2-keto-4-methyl-chromen-7-yl)oxyacetohydrazide;2-(4-methyl-2-oxo-chromen-7-yl)oxyacetohydrazide;2-(4-methyl-2-oxochromen-7-yl)oxyacetohydrazide;2-(4-methyl-2-oxo-chromen-7-yl)oxyethanehydrazide;2-[(4-methyl-2-oxo-7-chromenyl)oxy]acetohydrazide;Acethydrazide, 2-(4-methyl-7-coumarinyloxy)-;Acetic acid, ((4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy)-, hydrazide
• CAS NO: 69321-36-4
• Molecular Formula: C₁₂H₁₂N₂O₄
• Molecular Weight: 248.24
• Mol File: 69321-36-4.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 557.8°C at 760 mmHg
• Flash Point: 291.1°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 1.78E-12mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: (4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE(69321-36-4)
• EPA Substance Registry System: (4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE(69321-36-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 69321-36-4(Hazardous Substances Data)

Usage

General Description

(4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE is a chemical compound with potential pharmaceutical applications. It is a hydrazide derivative of acetic acid, and its structure includes a chromen-2-one ring with a methyl group and an acetic acid hydrazide side chain. (4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE has been studied for its potential as an anti-inflammatory and anti-cancer agent, as well as for its antimicrobial and antiviral properties. Research has shown that (4-METHYL-2-OXO-2H-CHROMEN-7-YLOXY)-ACETIC ACID HYDRAZIDE has the potential to inhibit the growth of various cancer cell lines and bacteria, making it a promising candidate for further drug development.

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

• 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 
• 89316-64-3 methyl 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetate 

Downstream Products

• 69560-78-7 2-Mercapto-5-(4-methyl-7-cumarinyloximethyl)-1,3,4-oxadiazol 
• 69321-35-3 N-(4-bromophenyl)-2-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)hydrazinecarbothioamide 
• 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 

Relevant articles and documents

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.

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.

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.