1-(4-Methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HCID 1476756CAS 338747-41-4

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Grundinformationen

Standard-SMILES: COc1ccc(Cn2cc(C(=O)O)c(=O)c3ccccc32)cc1
InChIKey: BZBBTGCKPRSPGF-UHFFFAOYSA-N
Summenformel: C18H15NO4
Durchschnittliche Molmasse: 309,3 g/mol
Monoisotopische Masse: 309,10010796

Überblick

BQCA is an organic molecular entity.

Namen und Bezeichner

Bevorzugter Name: 1-(4-Methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
IUPAC: 1-[(4-methoxyphenyl)methyl]-4-oxoquinoline-3-carboxylic acid
Englischer Name: 1-(4-Methoxybenzyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
Summenformel: C18H15NO4
Molmasse: 309.32

Namen und Synonyme

1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidBQCA compoundRefChem:907376BQCA338747-41-41-[(4-methoxyphenyl)methyl]-4-oxoquinoline-3-carboxylic acid1-(4-methoxybenzyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acidMFCD01315710CHEMBL608112BZBBTGCKPRSPGF-UHFFFAOYSA-NBQCA?BQCA-azo-IR353

Weitere Namen anzeigen

BQCA, 10 mM in DMSOBenzyl quinolone carboxylic acidmAChR,Muscarinic acetylcholine receptor,Inhibitor,inhibit,BQCA1-(4-Methoxybenzyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic ...3-Quinolinecarboxylic acid, 1,4-dihydro-1-[(4-methoxyphenyl)methyl]-4-oxo-

Oprea1_185678MLS000755157orb1223145orb1303464SCHEMBL1549479SCHEMBL31653939DTXSID20363104CHEBI:232407

Datenbank-Bezeichner

CAS: 338747-41-4
PubChem CID: 1476756
DTXSID: DTXSID20363104
ChEMBL: CHEMBL608112
ChEBI: CHEBI:232407
EC Number: 803-580-0
Nikkaji: J2.840.591J

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,4
Polarare Oberfläche (TPSA): 66,8 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 4
Schwere Atome: 23
Formalladung: 0
Komplexität: 493

Physikochemische Eigenschaften

Schmelzpunkt: 210 · 210-212 °C
Siedepunkt: 492.6 · 492.6±45.0 °C(Predicted)
Dichte: 1.346 · 1.346±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
Löslichkeit: 10 mg/mL · DMSO: soluble10mg/mL (clear solution)
pka: 0.7 · 0.70±0.20(Predicted)
Aggregatzustand: powder
Farbe: white to beige
InChI: 1S/C18H15NO4/c1-23-13-8-6-12(7-9-13)10-19-11-15(18(21)22)17(20)14-4-2-3-5-16(14)19/h2-9,11H,10H2,1H3,(H,21,22)
InChIKey: BZBBTGCKPRSPGF-UHFFFAOYSA-N
SMILES: COc1ccc(CN2C=C(C(O)=O)C(=O)c3ccccc23)cc1

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk: 3
risk_code: 22
hazard_code: Xn
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 Oral

Chemie und Industrie

Anwendungen · 1 Eintrag

BeschreibungBQCA is a highly selective positive allosteric modulator of the M1 muscarinic acetylcholine receptor (mAChR), as it dose-dependently reduces the concentration of acetylcholine required to activate the M1 receptor. The effective range for potentiation of M1 in cells by BQCA is 0.1 to 100 μM with an inflection point value of 845 nM when 3 nM acetylcholine is used. BQCA displays no potentiation, agonism, or antagonism at other mAChRs at concentrations up to 100 μM. It has excellent brain penetration and increases the firing rate of medial prefrontal cortex neurons in vivo in rats. BQCA prevents scopolamine-induced memory deficits in both contextual fear conditioning and a spontaneous alternation task in mice. It also restores impairment in reversal learning in a mouse model of Alzheimer’s disease and improves memory performance in rats.