Deoxyvasicinone

Base Information

• Chemical Name: Deoxyvasicinone
• CAS No.: 530-53-0
• Molecular Formula: C11H10 N2 O
• Molecular Weight: 186.213
• Hs Code.: 2933990090
• NSC Number: 159478
• DSSTox Substance ID: DTXSID90201049
• Nikkaji Number: J324.098C
• Wikidata: Q27106382
• Metabolomics Workbench ID: 67833
• ChEMBL ID: CHEMBL456881
• Mol file: 530-53-0.mol

Synonyms:2,3-trimethylene-4-quinazolone;deoxyvasicinone

Chemical Property of Deoxyvasicinone

Chemical Property:

• Vapor Pressure: 6.2E-05mmHg at 25°C
• Boiling Point: 345.3°Cat760mmHg
• Flash Point: 162.6°C
• PSA: 34.89000
• Density: 1.36g/cm³
• LogP: 1.34270
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 186.079312947
• Heavy Atom Count: 14
• Complexity: 298

Purity/Quality:

97% ^*data from raw suppliers

Deoxyvasicinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=NC3=CC=CC=C3C(=O)N2C1

Technology Process of Deoxyvasicinone

There total 79 articles about Deoxyvasicinone 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: 99.5%

1-(2-azidobenzoyl)azacyclopent-2-one (125659-45-2) → deoxyvasicinone (530-53-0)

Guidance literature:

With tributylphosphine; In xylene; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)99230-X

Reference yield: 95.0%

2-(3-hydroxypropyl)quinazolin-4(3H)-one (31431-93-3) → deoxyvasicinone (530-53-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo010727l

Reference yield: 92.0%

2-pyrrolidinon (616-45-5) + 2-carbomethoxyaniline (134-20-3) → deoxyvasicinone (530-53-0)

Guidance literature:

With trichlorophosphate; In toluene; for 5h; Reflux;

DOI:10.1016/j.bioorg.2021.105354

upstream raw materials:

2-pyrrolidinon

N-hydroxymethyl-anthranilic acid-lactone

2-methoxy-1-pyrroline

anthranilic acid

Downstream raw materials:

2-(pyrrolidin-1-ylmethyl)benzenamine

9-(3'-hydroxy-4'-methoxybenzylidene)deoxyvasicinone

3-[1-(4-Amino-phenyl)-meth-(E)-ylidene]-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one

3-[1-p-Tolyl-meth-(E)-ylidene]-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one

Refernces

Biotransformation of desoxypeganine by microsomal enzymes of the rabbit liver

10.1002/ardp.200400921

The research details an in vitro study on the biotransformation of Desoxypeganine, an anticholinergic quinazoline alkaloid, by rabbit liver microsomal enzymes. The purpose of the study was to investigate the metabolic pathways and kinetics of Desoxypeganine, which has therapeutic potential for Alzheimer's disease, alcoholism, and nicotine dependence. The researchers used aerobic incubation with rabbit liver homogenates as the enzyme source, supplemented with NADPH, and identified metabolites through high-performance liquid chromatography and mass spectrometry. The main conclusion was that Desoxypeganine is readily oxidized to its inactive metabolite Pegenone, which poses a challenge for dosage in pharmaceutical formulations. Key chemicals used in the process included Desoxypeganine, Pegenone, Vasicinone, Isovasicinone, NADPH, and various buffer solutions for the incubation and extraction steps.

Synthesis and bactericidal activity of 6-H(nitro)-9- arylidenedeoxyvasicinones and their perchlorates

10.1007/s10600-008-9105-0

The research focuses on the synthesis and bactericidal activity of 6-H(nitro)-9-arylidenedeoxyvasicinones and their perchlorates. Deoxyvasicinone and 6-nitrodeoxyvasicinone were reacted with various aromatic aldehydes, including 3,4-dimethoxybenzaldehyde, isovanillin, 2-bromoisovanillin, 5-bromovanillin, and furfurol, in glacial acetic acid to produce a series of target compounds (2a-e and 3a-i). These compounds were characterized by IR, PMR, and mass spectra. The study also involved the preparation of perchlorates (4a-i) by heating the synthesized compounds in acetic acid in the presence of concentrated HClO4. The synthesized compounds were tested for their bactericidal properties against various gram-positive and gram-negative bacterial strains, showing moderate to low activity.

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