3813-92-1

Basic information

• Product Name: 4(1H)-Quinolinone, 2-(4-methoxyphenyl)-
• Synonyms: 2-(4-methoxyphenyl)-quinolin-4(1H)-one;2-(p-methoxyphenyl)-quinolin-4(1H)-one;2-(4-Methoxy-phenyl)-1H-quinolin-4-one;2-(4-methoxyphenyl)-4-quinolone;2-(4-methoxyphenyl)-1H-quinolin-4-one;2-(4-methoxyphenyl)quinolin-4(1H)-one
• CAS NO: 3813-92-1
• Molecular Formula: C16H13NO2
• Molecular Weight: 251.285
• Mol File: 3813-92-1.mol
• Article Data: 35

Chemical Properties

• Melting Point: 176 - 177 °C (acetone)
• Boiling Point: 418.7±45.0 °C(Predicted)
• Density: 1.206±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4(1H)-Quinolinone, 2-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(1H)-Quinolinone, 2-(4-methoxyphenyl)-(3813-92-1)
• EPA Substance Registry System: 4(1H)-Quinolinone, 2-(4-methoxyphenyl)-(3813-92-1)

Safety Data

• Hazardous Substances Data: 3813-92-1(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 768-60-5 4-methoxyphenylacetylen 
• 5234-26-4 N-(2-acetylphenyl)acetamide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 74965-38-1 tert-butyl (2-formylphenyl)carbamate 
• 164226-32-8 2-(tert-butyloxycarbonyl)aminobenzyl alcohol 
• 1622382-07-3 tert-butyl {2-[1-hydroxy-3-(4-methoxyphenyl)prop-2-yn-1-yl]phenyl}carbamate 
• 1622382-17-5 1-(2-aminophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-ol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1203669-21-9 1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one 
• 1357394-80-9 1-(2-bromophenyl)-3-(4-methoxyphenyl)-prop-2-yn-1-ol 
• 577-59-3 2-acetylnitrobenzene 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1375678-88-8 C₁₆H₁₂ClNO₂ 
• 246181-55-5 1-methyl-2-(4’-methoxyphenyl)-1H-4-quinolone 
• 21202-79-9 4-chloro-2-(4-methoxy)phenyl quinoline 
• 502841-05-6 4-chloro-3-bromo-2-(4-methoxyphenyl)quinoline 
• 876460-09-2 3-iodo-2-(4'-methoxyphenyl)-1-methylquinolin-4(1H)-one 
• 502841-12-5 3-bromo-2-(4'-methoxyphenyl)quinolin-4(1H)-one 
• 882866-44-6 3-iodo-2-(4'-methoxyphenyl)-quinolin-4(1H)-one 

Relevant articles and documents

QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF

The present invention relates to quinolones of formula (I) and process for its preparation by amine insertion into aryl-ynones thereof. [Formula I] The invention further relates to the process to obtain the natural products such as: graveoline, graveolinine, pseudane IV, pseudane VII, pseudane VIII and pseudane XII. The invention also describes the process for the total synthesis of waltherione F in concise approach from the quinolone synthesized. [Formula II]

In quest of small-molecules as potent non-competitive inhibitors against influenza

A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.

Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F

An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.