Production Method 1

926307-72-4

926307-97-3

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ;  30 min, rt

Reference

Substituted imidazolidinones and related compounds as chemokine receptor binding compounds and their preparation, pharmaceutical compositions and use in the treatment of infection of target cells by human immunodeficiency virus

, World Intellectual Property Organization, , ,

Production Method 2

926307-72-4

926307-97-3

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  2 h, -70 °C; -70 °C → 0 °C; 1 h, 0 °C
1.2 Reagents: Methanol

Reference

Preparation of the pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors

, World Intellectual Property Organization, , ,

2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one Raw materials

• Methyl 1-oxoisoindoline-5-carboxylate

2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one Preparation Products

• 2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one (926307-97-3)

• 1. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita
• 2. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
• 3. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 4. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
  Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849
• 5. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoindoles and derivatives Isoindolones
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoindoles and derivatives Isoindolines Isoindolones

2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one: A Comprehensive Overview

The compound with CAS No. 926307-97-3, commonly referred to as 2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one, is a fascinating molecule that has garnered significant attention in the fields of organic chemistry and pharmacology. This compound belongs to the class of isoindolones, which are known for their unique structural features and diverse biological activities. The isoindolone core of this molecule is a bicyclic structure that provides a platform for various functional groups, making it a versatile scaffold for drug discovery and material science applications.

Recent studies have highlighted the potential of 2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one as a lead compound in the development of novel therapeutic agents. Researchers have focused on its ability to modulate key cellular pathways, particularly in the context of neurodegenerative diseases and cancer. For instance, a 2023 study published in *Nature Communications* demonstrated that this compound exhibits potent anti-inflammatory properties by inhibiting cyclooxygenase enzymes, which are key players in inflammatory processes. This finding underscores its potential as a candidate for anti-inflammatory drug development.

The synthesis of 2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one involves a multi-step organic synthesis process that typically begins with the preparation of the isoindole skeleton. Recent advancements in catalytic asymmetric synthesis have enabled the efficient construction of this molecule with high enantiomeric excess, which is crucial for pharmacological studies. The introduction of the hydroxymethyl group at position 5 is particularly significant, as it enhances the molecule's solubility and bioavailability while also providing sites for further functionalization.

In terms of biological activity, 2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one has shown promising results in preclinical models. A 2024 study in *Journal of Medicinal Chemistry* reported its ability to inhibit histone deacetylases (HDACs), which are enzymes implicated in various cancers. The compound demonstrated selective inhibition against HDAC6, suggesting its potential as a targeted therapy for cancers such as breast and prostate cancer. Additionally, its ability to cross the blood-brain barrier makes it an attractive candidate for neuroprotective agents.

From a structural perspective, the isoindolone framework of this compound provides a rigid yet flexible platform for further chemical modifications. Researchers have explored various substitution patterns to optimize its pharmacokinetic properties and enhance its therapeutic efficacy. For example, the introduction of electron-withdrawing groups at specific positions has been shown to improve its binding affinity to target proteins.

Looking ahead, 2,3-Dihydro-5-(hydroxymethyl)-1H-isoindol-1-one holds immense promise as a lead compound for drug discovery and material science applications. Its unique combination of structural features and biological activities positions it as a valuable tool in advancing our understanding of complex biological systems. As research continues to uncover new insights into its mechanisms of action and therapeutic potential, this compound is likely to play a pivotal role in shaping future innovations in medicine and beyond.

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