58632-48-7

Basic information

• Product Name: Carbamic acid, (4-methyl-2-oxo-2H-1-benzopyran-7-yl)-, ethyl ester
• Synonyms: Carbamic acid, (4-methyl-2-oxo-2H-1-benzopyran-7-yl)-, ethyl ester;(4-Methyl-2-oxo-2H-1-benzopyran-7-yl)carbamic acid ethyl ester;ethyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamate
• CAS NO: 58632-48-7
• Molecular Formula: C₁₃H₁₃NO₄
• Molecular Weight: 247.25
• Mol File: 58632-48-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 358.4°Cat760mmHg
• Flash Point: 170.6°C
• Appearance: /
• Density: 1.294g/cm³
• Vapor Pressure: 2.55E-05mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: Carbamic acid, (4-methyl-2-oxo-2H-1-benzopyran-7-yl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (4-methyl-2-oxo-2H-1-benzopyran-7-yl)-, ethyl ester(58632-48-7)
• EPA Substance Registry System: Carbamic acid, (4-methyl-2-oxo-2H-1-benzopyran-7-yl)-, ethyl ester(58632-48-7)

Safety Data

• Hazardous Substances Data: 58632-48-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 1153, 1990 DOI: 10.1002/jhet.5570270464

InChI:InChI=1/C13H13NO4/c1-3-17-13(16)14-9-4-5-10-8(2)6-12(15)18-11(10)7-9/h4-7H,3H2,1-2H3,(H,14,16)

Upstream product

• 141-97-9 ethyl acetoacetate 
• 7159-96-8 ethyl N-(3-hydroxyphenyl)carbamate 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 591-27-5 m-Hydroxyaniline 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 26093-31-2 7-amino-4-methylcoumarin. 
• 75957-52-7 7-(N^α-benzyloxycarbonyl-α-benzyl-γ-L-glutaminyl)-4-methylcoumarinylamide 
• 72669-53-5 L-glutamic acid γ-(7-amido-4-methylcoumarin) 
• 1346523-56-5 7-[ethyl-(4-methanesulfonylphenyl)amino]-4-methylcoumarin 
• 1346523-57-6 7-[(4-methanesulfonylphenyl)octylamino]-4-methylcoumarin 
• 1346523-59-8 4-{[ethyl-(4-methylcoumarin-7-yl)amino]methyl}benzoic acid methyl ester 
• 1346523-60-1 4-{[(4-methylcoumarin-7-yl)octylamino]methyl}benzoic acid methyl ester 
• 1346523-61-2 4-{[ethyl-(4-methylcoumarin-7-yl)amino]methyl}benzoic acid 
• 1346523-62-3 4-{[(4-methylcoumarin-7-yl)octylamino]methyl}benzoic acid 
• 28821-18-3 4-methyl-7-ethylamino-2H-benzopyran-2-one 
• 101973-09-5 7-[N-(p-toluenesulfonyl)amino]-4-methylcoumarin 
• 1415908-44-9 8-methyl-2-styrylchromeno[7,6-d]imidazol-6(3H)-one 

Relevant articles and documents

Intracellular detection of hazardous Cd2+ through a fluorescence imaging technique by using a nontoxic coumarin based sensor

A new coumarin based turn on fluorescent sensor (R1) was reported for the detection of highly hazardous Cd2+ with excellent selectivity and sensitivity without any interference of other metal ions. The single crystal X-ray structure analysis of

Discovery of unique thiazolidinone-conjugated coumarins as novel broad spectrum antibacterial agents

Unique coumarin conjugates with thiazolidinone as novel structural antibacterial modulators were exploited to combat the lethal multidrug-resistant bacterial infections. Bioactivity evaluation identified that indole-incorporated coumarin thiazolidinone conjugate 14a with low cytotoxicity to mammalian cells showed a broad antibacterial spectrum and exerted potent inhibition efficiencies to the tested germs at low concentrations (0.25–2 μg/mL). Moreover, the favorable performance of 14a in eradicating bacterial biofilm was beneficial to avert developing drug resistance. Mechanistic explorations revealed that molecule 14a was able to destroy cell membrane, leading to the leakage of intracellular materials and metabolism inhibition. The accumulation of excess reactive oxygen species (ROS) mediated by compound 14a could impede glutathione (GSH) activity and induce lipid peroxidation to suppress bacteria growth. Furthermore, compound 14a could not only intercalate into DNA base pair but also take part in non-covalent interaction with DNA gyrase B to hinder their biological function. Quantum chemical study indicated that molecule 14a had low HOMO-LUMO energy gap, which resulted in more stabilizing interactions and was conducive to displaying better antibacterial activity. ADMET analysis manifested that 14a possessed promising pharmacokinetic properties.

Evaluation of novel coumarin-proline sulfonamide hybrids as anticancer and antidiabetic agents

Cancer and diabetes are considered as two major diseases affecting human health worldwide. Various therapies are available for treatment of cancer and diabetes individually, peptide linkage containing proline sulfonamide can be a promising therapy for treatment of both cancer as well as diabetes. Here, we report design and synthesis of novel coumarin-proline sulfonamide derivatives as anticancer and antidiabetic agents. All the synthesized compounds were screened for their anticancer activity against lungs cancer cell line (A549) and breast cancer cell line (MCF7) using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide dye (MTT)assay and antidiabetic activity using DPP-IV inhibition assay. Compound 16b showed excellent activity against breast cancer cell line (MCF7) with IC50 value of 1.07 μM. All compounds showed moderate DPP-IV inhibition.