1,5-Isoquinolinediol

Base Information

• Chemical Name: 1,5-Isoquinolinediol
• CAS No.: 5154-02-9
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29337900
• European Community (EC) Number: 637-104-6
• NSC Number: 65585
• DSSTox Substance ID: DTXSID60199505
• Nikkaji Number: J410.618K
• Wikidata: Q27132988
• Pharos Ligand ID: JBSLV6BW8VY6
• Metabolomics Workbench ID: 63107
• ChEMBL ID: CHEMBL338314
• Mol file: 5154-02-9.mol

Synonyms:1,5-dihydroxyisoquinoline;1,5-isoquinolinediol

Chemical Property of 1,5-Isoquinolinediol

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 3.18E-09mmHg at 25°C
• Melting Point: 270-275 °C
• Refractive Index: 1.639
• Boiling Point: 463.8 °C at 760 mmHg
• PKA: 8.52±0.20(Predicted)
• Flash Point: 234.3 °C
• Density: 1.337 g/cm3
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >36 mg/mL
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 161.047678466
• Heavy Atom Count: 12
• Complexity: 225

Purity/Quality:

98%, ^*data from raw suppliers

1,5-Isoquinolinediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CNC2=O)C(=C1)O
• Description: The poly(ADP-ribose) polymerases (PARPs) form a family of enzymes with roles in DNA repair and apoptosis. 1,5-Isoquinolinediol is an inhibitor of poly(ADP-ribose) synthetase (PARP1; IC50 = 0.39 μM). It has been used to study the role of PARP1 in both DNA repair and oxidant stress-induced cell death. This compound can be used with cells in culture and in animals.
• Uses: 1,5-Isoquinolinediol can be used as a reagent in the preparation of PARP inhibitor. Reagent used in the preparation of PARP inhibitor.

Technology Process of 1,5-Isoquinolinediol

There total 4 articles about 1,5-Isoquinolinediol 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: 60.0%

5-Hydroxyisochinolin-2-oxid (90347-99-2) → 1,5-dihydroxy-1(2H)-isoquinoline (5154-02-9)

Guidance literature:

5-Hydroxyisochinolin-2-oxid; With acetic anhydride; at 140 ℃; for 4h;

With sodium methylate; In methanol; Further stages.;

DOI:10.1016/j.bmcl.2008.03.027

Reference yield:

→ isoquinoline-1,5-diol (5154-02-9)

Guidance literature:

With potassium hydroxide; at 220 - 230 ℃;

DOI:10.1021/ja01200a028

Reference yield:

5-(benzyloxy)-1-hydroxyisoquinoline (144242-87-5) → 1,5-dihydroxy-1(2H)-isoquinoline (5154-02-9)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1021/jm00101a022

upstream raw materials:

5-(benzyloxy)-1-hydroxyisoquinoline

5-Hydroxyisochinolin-2-oxid

Downstream raw materials:

C₂₄H₂₅N₃O₄

5-(benzyloxy)-1-hydroxyisoquinoline

3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone

isoquinoline-1-oxide

Refernces

• 1、 -. "Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process". . . Retrieved 2008/06/13.