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

Base Information

• Chemical Name: 1-(4-Methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 338747-41-4
• Molecular Formula: C₁₈H₁₅NO₄
• Molecular Weight: 309.321
• Hs Code.: 2933499090
• European Community (EC) Number: 803-580-0
• DSSTox Substance ID: DTXSID20363104
• Nikkaji Number: J2.840.591J
• Wikidata: Q82146669
• ChEMBL ID: CHEMBL608112
• Mol file: 338747-41-4.mol

Synonyms:1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;BQCA compound;sodium 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

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

Chemical Property:

• Melting Point: 210-212 °C
• Boiling Point: 492.6±45.0 °C(Predicted)
• PKA: 0.70±0.20(Predicted)
• PSA: 68.53000
• Density: 1.346±0.06 g/cm3(Predicted)
• LogP: 2.75660
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble10mg/mL (clear solution)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 309.10010796
• Heavy Atom Count: 23
• Complexity: 493

Purity/Quality:

99% ^*data from raw suppliers

BQCA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CN2C=C(C(=O)C3=CC=CC=C32)C(=O)O
• Description: BQCA 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.
• Uses: BQCA is a highly selective positive allosteric modulator of the M1 muscarinic acetylcholine receptor (mAChR).

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

There total 2 articles about 1-(4-Methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1,4-Dihydro-4-oxo-quinoline-3-carbonitrile (71083-59-5) → 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (338747-41-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / Reflux

2: acetic acid; sulfuric acid / 50 °C / Reflux

With sulfuric acid; sodium hydride; acetic acid; In tetrahydrofuran;

DOI:10.1002/adsc.201900286

Reference yield:

→ 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (338747-41-4)

Guidance literature:

Reference yield:

1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (338747-41-4) → 2-( 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxamido)acetic acid

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.03 h

1.2: 18 h / 20 °C

2.1: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C

With water; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

1,4-Dihydro-4-oxo-quinoline-3-carbonitrile