369651-81-0

Basic information

• Product Name: 4-hydroxy-1-phenyl-3-propyl-2(1H)-quinolinone
• Synonyms: 4-hydroxy-1-phenyl-3-propyl-2(1H)-quinolinone
• CAS NO: 369651-81-0
• Molecular Formula: C₁₈H₁₇NO₂
• Molecular Weight: 279.33308
• Mol File: 369651-81-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-hydroxy-1-phenyl-3-propyl-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-1-phenyl-3-propyl-2(1H)-quinolinone(369651-81-0)
• EPA Substance Registry System: 4-hydroxy-1-phenyl-3-propyl-2(1H)-quinolinone(369651-81-0)

Safety Data

• Hazardous Substances Data: 369651-81-0(Hazardous Substances Data)

Upstream product

• 122-39-4 diphenylamine 
• 2163-48-6 diethyl propylmalonate 

Downstream Products

• 369651-52-5 3-hydroxy-1-phenyl-3-propyl-2,4(1H,3H)-quinolinedione 

Relevant articles and documents

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

Novel ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones in aqueous alkali. The first convenient route to 2-hydroxyindoxyls

Ring contraction of 3-hydroxy-2,4(1H, 3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.