2-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONE

Base Information

• Chemical Name: 2-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONE
• CAS No.: 6890-08-0
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.1568
• Hs Code.: 2933499090
• Mol file: 6890-08-0.mol

Synonyms:1,3(2H,4H)-Isoquinolinedione, 2-hydroxy-; 2-Hydroxyisoquinoline-1,3(2H,4H)-dione

Chemical Property of 2-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONE

Chemical Property:

• Vapor Pressure: 1.53E-06mmHg at 25°C
• Melting Point: 197-200°C
• Refractive Index: 1.67
• Boiling Point: 382.7°C at 760 mmHg
• Flash Point: 185.3°C
• PSA: 57.61000
• Density: 1.51g/cm³
• LogP: 0.53860
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

2-Hydroxyisoquinoline-1,3(2H,4H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 2-Hydroxyisoquinoline-1,3(2H,4H)-dione derivatives exhibit potential as inhibitors of HIV-1 integrase, with certain alkylated variants demonstrating low micromolar inhibitory activity. However, their effectiveness is limited by high cytotoxicity and poor inhibition of the reverse transcriptase RNase H domain. Despite these challenges, these compounds serve as a promising foundation for further optimization in the development of novel antiviral agents.

Technology Process of 2-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONE

There total 6 articles about 2-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONE 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: 86.0%

2-benzyloxyisoquinoline-1,3(2H,4H)-dione (611187-05-4) → 2-hydroxyisoquinoline-1,3(2H,4H)-dione (6890-08-0)

Guidance literature:

2-benzyloxyisoquinoline-1,3(2H,4H)-dione; With boron tribromide; In dichloromethane; at 20 ℃;

With water; In dichloromethane; at 20 ℃;

DOI:10.1021/jm8007085

Reference yield: 76.0%

2-methoxyisoquinoline-1,3(2H,4H)-dione (22367-15-3) → 2-hydroxyisoquinoline-1,3(2H,4H)-dione (6890-08-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c4cc08407a

Reference yield:

Homophthalic acid (89-51-0) → 2-hydroxyisoquinoline-1,3(2H,4H)-dione (6890-08-0)

Guidance literature:

Multi-step reaction with 2 steps

1: xylene

2: palladium/strontium carbonate; butanone / Hydrogenation

With Pd/SrCO₃; butanone; xylene;

DOI:10.1039/jr9550003518

upstream raw materials:

2-benzyloxyisoquinoline-1,3(2H,4H)-dione

Homophthalic acid

2-methoxyisoquinoline-1,3(2H,4H)-dione

N-methoxybenzamide

Refernces

2-Hydroxyisoquinoline-1,3(2H,4H)-diones as inhibitors of HIV-1 integrase and reverse transcriptase RNase H domain: Influence of the alkylation of position 4

10.1016/j.ejmech.2010.11.033

This research presents the synthesis and evaluation of a series of 2-hydroxyisoquinoline-1,3(2H,4H)-dione derivatives as potential inhibitors of HIV-1 integrase and reverse transcriptase RNase H domain. The purpose of the study was to develop new anti-HIV agents that could overcome the limitations of existing therapies, such as high costs, side effects, and drug resistance. The researchers introduced alkyl and arylalkyl groups at position 4 of the 2-hydroxyisoquinoline-1,3(2H,4H)-dione scaffold to investigate the influence of these substitutions on enzymatic inhibitory and antiviral activities. The chemicals used in the process included various alkyl and arylalkyl halides for alkylation, O-benzylhydroxylamine for cyclization, and boron tribromide or trichloride for deprotection. The study concluded that while all compounds showed poor inhibitory properties against HIV-1 reverse transcriptase RNase H, four compounds demonstrated low micromolar level inhibition of HIV-1 integrase. However, high cellular cytotoxicity limited their potential as antiviral agents. Despite this, the identified integrase inhibitors provided a good basis for the development of new antiviral hits. The study also included docking studies using crystallographic data to explain the improved integrase inhibitory activities of certain compounds.

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