Ponalrestat

Base Information

• Chemical Name: Ponalrestat
• CAS No.: 72702-95-5
• Molecular Formula: C17H12 Br F N2 O3
• Molecular Weight: 391.196
• Hs Code.: 2933990090
• UNII: 2CV0A5G64E
• DSSTox Substance ID: DTXSID1045665
• Nikkaji Number: J22.229A
• Wikidata: Q27164918
• NCI Thesaurus Code: C82173
• Pharos Ligand ID: XXLHFSP1UXM6
• ChEMBL ID: CHEMBL7679
• Mol file: 72702-95-5.mol

Synonyms:3-(4-bromo-2-fluorobenzyl)-3,4-dihydro-4-oxo-3H-phthalazin-1-ylacetic acid;ICI 128436;ICI-128436;ponalrestat;Statil

Chemical Property of Ponalrestat

Chemical Property:

• Vapor Pressure: 4.01E-14mmHg at 25°C
• Melting Point: 184-186℃ (DEC.)
• Boiling Point: 576.3°C at 760 mmHg
• Flash Point: 302.4°C
• PSA: 72.19000
• Density: 1.60
• LogP: 2.97350
• Storage Temp.: Store at RT
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 390.00153
• Heavy Atom Count: 24
• Complexity: 542

Purity/Quality:

≥98.0%, ^*data from raw suppliers

Statil ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=NN(C2=O)CC3=C(C=C(C=C3)Br)F)CC(=O)O
• Description: Statil is an aldose reductase inhibitor that blocks the conversion of glucose to sorbitol. It demonstrates selectivity for aldose reductase 2 over aldose reductase 1 with Ki values of 7.7 nM and 60 μM, respectively. Statil has been shown to prevent diabetes-induced alterations of the cardiovascular system in 14-day streptozotocin-diabetic rats. Aldose reductase inhibition by statil has also been used to impair the synthesis of prostaglandin F2α by human cultured preadipocytes.
• Uses: Inhibitor (aldose reductase). Statil is a knon aldose reductase inhibitor which blocks the conversion of glucose to sorbitol. In addition it suppresses cell cancer growth

Technology Process of Ponalrestat

There total 2 articles about Ponalrestat 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: 54.0%

4-bromo-2-fluorobenzyl bromide (76283-09-5) + ethyl 1,2-dihydro-1-oxophthalazin-4-ylacetate (25947-13-1) → ponalrestat (72702-95-5)

Guidance literature:

ethyl 1,2-dihydro-1-oxophthalazin-4-ylacetate; With sodium hydroxide; In tetrahydrofuran; at 40 - 50 ℃; for 0.5h;

4-bromo-2-fluorobenzyl bromide; In tetrahydrofuran; at 50 - 60 ℃; for 2h;

With acetic acid; In tetrahydrofuran; water; pH=2 - 3;

DOI:10.1111/j.1747-0285.2010.00947.x

Reference yield:

→ ponalrestat (72702-95-5)

Guidance literature:

Reference yield: 90.0%

ponalrestat (72702-95-5) + 4-chloro-aniline (106-47-8) → 2-(2-(4-bromo-2-fluorobenzyl)-1,2-dihydro-1-oxo-phthalazin-4-yl)-N-(4-chlorophenyl)acetamide (1226760-02-6)

Guidance literature:

ponalrestat; With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 4 ℃; for 0.5h;

4-chloro-aniline; In dichloromethane;

DOI:10.1111/j.1747-0285.2010.00947.x

upstream raw materials:

4-bromo-2-fluorobenzyl bromide

ethyl 1,2-dihydro-1-oxophthalazin-4-ylacetate

Downstream raw materials:

2-(4-bromo-2-fluorobenzyl)-4-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)phthalazin-1(2H)-one

2-(2-(4-bromo-2-fluorobenzyl)-1,2-dihydro-1-oxo-phthalazin-4-yl)-N-(5-nitrothiazol-2-yl)acetamide

2-(4-bromo-2-fluorobenzyl)-4-(2-oxo-2-(2-(4-pyridin-2-yl)piperazin-1-yl)ethyl)phthalazin-1(2H)-one

2-(4-bromo-2-fluorobenzyl)-4-(2-(4-benzylpiperazin-1-yl)-2-oxoethyl)phthalazin-1(2H)-one

Refernces

• 1、 -. "USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS". . . Retrieved 2008/06/13.