530-52-9

Basic information

• Product Name: furo[2,3-b]quinolin-4(9H)-one
• Synonyms: Furo[2,3-b]quinolin-4(9H)-one
• CAS NO: 530-52-9
• Molecular Formula: C₁₁H₇NO₂
• Molecular Weight: 185.1788
• Mol File: 530-52-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 249 °C
• Boiling Point: 335.5°C at 760 mmHg
• Flash Point: 156.7°C
• Density: 1.309g/cm³
• Vapor Pressure: 0.00012mmHg at 25°C
• Refractive Index: 1.618
• PKA: -0.13±0.20(Predicted)
• CAS DataBase Reference: furo[2,3-b]quinolin-4(9H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: furo[2,3-b]quinolin-4(9H)-one(530-52-9)
• EPA Substance Registry System: furo[2,3-b]quinolin-4(9H)-one(530-52-9)

Safety Data

• Hazardous Substances Data: 530-52-9(Hazardous Substances Data)

Upstream product

• 111163-82-7 4-chlorofuro[2,3-b]quinoline 
• 484-29-7 dictamnine 
• 74120-99-3 2,3,4,9-Tetrahydrofuro<2,3-b>quinoline-3,4-dione 

Downstream Products

• 484-74-2 iso-dictamnine 
• 484-29-7 dictamnine 
• 479077-78-6 1-[3-(furo[2,3-b]quinolin-4-ylamino)phenyl]ethanone 
• 479077-76-4 1-[4-(furo[2,3-b]quinolin-4-ylamino) phenyl]ethanone 
• 627086-17-3 4-chlorofuro[3,2-c]quinoline 
• 1158850-18-0 9-(4-phenoxybutyl)furo[2,3-b]quinolin-4(9H)-one 
• 1158850-16-8 4-(4-phenoxybutoxy)furo[2,3-b]quinoline 

Relevant articles and documents

Microsomal metabolism of dictamnine: Identification of metabolites and evaluation of their mutagenicity in Salmonella typhimurium

Incubation of the furoquinoline alkaloid dictamnine with microsomal fractions from phenobarbital-induced rat liver resulted in a metabolite mixture from which demethyldictamnine and dictamnic acid were identified by a GC-MS technique. The identity of the two compounds was confirmed by synthesis. Other metabolites were characterized by their mass spectra only. The pattern of the metabolites suggested a possible pathway of metabolism in vitro. We assume that the metabolism of dictamnine is analogous to the metabolism of the related 8-methoxypsoralen and takes place via an unstable epoxide and subsequent oxidative opening of the furan ring. Direct evidence for the formation of an epoxide was, however, not obtained. The identified compounds as well as some putative metabolites were shown to be non-mutagenic in Salmonella typhimurium TA98 except for 8-hydroxydictamnine, which, however, was not detected in the metabolite mixture.

4-Phenoxybutoxy-substituted heterocycles - A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3

The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC50 of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC50s of 150 nM to 10 μM in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC50 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers.

Synthesis and cytotoxic evaluation of some 4-anilinofuro[2,3-b]quinoline derivatives

Some 4-anilinofuro[2,3-b] quinoline derivatives were synthesized from dictamnine, a natural alkaloid, and evaluated for their cytotoxicity in the NCI's full panel of 60 human cancer cell lines derived from nine cancer cell types, including leukemia, non-s