Isochroman-4-one

Base Information

• Chemical Name: Isochroman-4-one
• CAS No.: 20924-56-5
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: 2932999099
• European Community (EC) Number: 819-563-6
• DSSTox Substance ID: DTXSID40491796
• Metabolomics Workbench ID: 96397
• Nikkaji Number: J340.020D
• Wikidata: Q72485186
• Mol file: 20924-56-5.mol

Synonyms:isochroman-4-one;20924-56-5;4-ISOCHROMANONE;3,4-dihydro-1H-2-benzopyran-4-one;1H-2-Benzopyran-4(3H)-one;1H-isochromen-4-one;1H-isochromen-4(3H)-one;MFCD09744058;1H-2-Benzopyran-4-ol, AldrichCPR;SCHEMBL135207;DTXSID40491796;OYXTZAZUFUWSIR-UHFFFAOYSA-N;BCP27335;AKOS006345298;CS-W003634;PB14717;AC-30171;AS-30739;SY030590;AM20030326;FT-0660890;A15365;EN300-111551;A815022;4-Isochromanone;Z1201625145

Chemical Property of Isochroman-4-one

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Melting Point: 48 °C
• Refractive Index: 1.562
• Boiling Point: 279.501 °C at 760 mmHg
• Flash Point: 134.664 °C
• PSA: 26.30000
• Density: 1.197g/cm³
• LogP: 1.39950
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 165

Purity/Quality:

99%, ^*data from raw suppliers

Isochroman-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC=CC=C2C(=O)CO1
• General Description: ISOCHROMAN-4-ONE, also known as 4-Isochromanone or 1H-Isochromen-4(3H)-one, is a key structural component in the development of dual-binding site acetylcholinesterase (AChE) inhibitors, particularly for Alzheimer's disease treatment. Its derivatives, when hybridized with an N-benzyl pyridinium moiety, exhibit potent AChE inhibitory activity, high selectivity, and favorable pharmacokinetic properties, making them promising candidates for enhancing cognitive function by modulating acetylcholine levels in the brain. The most effective derivative demonstrated exceptional inhibitory potency (IC50 = 0.15 nM) and selectivity, highlighting its potential as a lead compound for therapeutic development.

Technology Process of Isochroman-4-one

There total 1 articles about Isochroman-4-one 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: 72.0%

isochromane (493-05-0) → isochroman-1-one (4702-34-5) + isochroman-4-one (20924-56-5)

Guidance literature:

With carbon monoxide; oxygen; copper dichloride; palladium dichloride; In tert-butyl alcohol; for 72h; under 45600 Torr;

DOI:10.1246/cl.1994.1149

Reference yield: 89.5%

isochroman-4-one (20924-56-5) → isochroman-4-amine (147663-00-1)

Guidance literature:

With ammonia; hydrogen; In ethanol; at 95 ℃; for 9h; under 3750.38 - 30003 Torr; Autoclave; Inert atmosphere;

Reference yield: 30.0%

isochroman-4-one (20924-56-5) + p-Chlorothiophenol (106-54-7) → C15H11ClO2S

Guidance literature:

With di-tert-butyl peroxide; at 120 ℃; for 6h;

DOI:10.1055/s-0034-1380125

upstream raw materials:

isochromane

Downstream raw materials:

isochroman-4-amine

Refernces

Design, synthesis, biological evaluation, and docking study of 4-isochromanone hybrids bearing N-benzyl pyridinium moiety as dual binding site acetylcholinesterase inhibitors (part II)

10.1111/cbdd.13136

The study focuses on the design, synthesis, biological evaluation, and docking study of novel 4-isochromanone compounds bearing an N-benzyl pyridinium moiety, which were developed as dual-binding site acetylcholinesterase (AChE) inhibitors for potential use in treating Alzheimer's disease. The chemicals used in the study include a series of synthesized 4-isochromanone derivatives with varying substituents at different positions on the benzyl group and the 4-isochromanone skeleton. These compounds were evaluated for their inhibitory activities against AChE and butyrylcholinesterase (BuChE), selectivity, neurotoxicity, and plasma stability. The purpose of these chemicals was to serve as potential anti-Alzheimer's disease agents by increasing acetylcholine levels in the brain through the inhibition of cholinesterase enzymes, with the aim of improving cognitive functions. The most potent compound, 1q, showed an IC50 value of 0.15 nM against AChE and a high selectivity index (SI > 5903), indicating its potential as a lead compound for further development.

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