Tolimidone

Base Information

• Chemical Name: Tolimidone
• CAS No.: 41964-07-2
• Molecular Formula: C11H10N2O2
• Molecular Weight: 202.213
• Hs Code.: 2933599090
• European Community (EC) Number: 803-991-5
• NSC Number: 314335
• UNII: MU3JD8E9IS
• DSSTox Substance ID: DTXSID50194786
• Nikkaji Number: J16.876I
• Wikipedia: Tolimidone
• Wikidata: Q7814266
• NCI Thesaurus Code: C152683
• Pharos Ligand ID: HGQ51BAPVYBU
• Metabolomics Workbench ID: 144596
• ChEMBL ID: CHEMBL8030
• Mol file: 41964-07-2.mol

Synonyms:5-(3-methylphenoxy)-2(1H)-pyrimidinone;MLR-1023

Chemical Property of Tolimidone

Chemical Property:

• Melting Point: 163-164℃
• Refractive Index: 1.598
• PSA: 54.98000
• Density: 1.22 g/cm³
• LogP: 1.87060
• Storage Temp.: room temp
• Solubility.: DMSO: soluble15mg/mL (clear solution)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 202.074227566
• Heavy Atom Count: 15
• Complexity: 310

Purity/Quality:

99% ^*data from raw suppliers

MLR 1023 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)OC2=CNC(=O)N=C2
• Recent ClinicalTrials: An Add-on Study of MLR-1023 in Adults With Uncontrolled Type 2 Diabetes on Metformin Therapy
• Description: MLR-1023 is an allosteric activator of Lyn kinase (EC50 = 63 nM). It has no significant activity against a panel of related kinases. MLR-1023 is orally bioavailable and reduces blood glucose levels in mice subjected to an oral glucose tolerance test. This effect is insulin-dependent, with MLR-1023 increasing insulin receptor sensitivity. MLR-1023 produces a dose-dependent and durable glucose-lowering effect in chronically treated db/db mice without causing weight gain.
• Uses: Tolimidone (MLR-1023) is an allosteric Lyn kinase activator that has been shown to reduce blood glucose levels in mice. Studies show that Tolimidone is an effective insulin receptor-potentiating agent that is potentially capable of producing durable blood glucose-lowering activity in diabetics. Tolimidone is a candidate for the treatment of type 2 diabetes. Tolimidone (MLR-1023) is an allosteric Lyn kinase activator that has been shown to reduce blood glucose levels in mice. Studies show that Tolimidone is an effective insulin receptor-potentiating agent that is potentially capable of producing durable blood glucose-lowering activity in diabetics. Tolimidone is a candidate for the treatment of type 2 diabetes.

Technology Process of Tolimidone

There total 7 articles about Tolimidone 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: 85.6%

urea (57-13-6) + (E)-3-(dimethylamino)-2-(meta-tolyloxy)acrylaldehyde (53341-46-1) → 2(1H)-pyrimidinone, 5-(3-methylphenoxy) (41964-07-2)

Guidance literature:

urea; (E)-3-(dimethylamino)-2-(meta-tolyloxy)acrylaldehyde; With sodium methylate; In ethanol; at 77 ℃; for 2h;

With acetic acid; In water; at 60 ℃; pH=6;

Reference yield: 63.0%

C11H9N2O2(1-)*Na(1+) → 2(1H)-pyrimidinone, 5-(3-methylphenoxy) (41964-07-2)

Guidance literature:

With acetic acid; In water; at 60 ℃; Industrial scale;

Reference yield:

3-methylphenoxyacetaldehyde diethyl acetal (58042-45-8) → 2(1H)-pyrimidinone, 5-(3-methylphenoxy) (41964-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) POCl₃ / 1.) 50 deg C, 45 min, 2.) CHCl₃, reflux, 3 h

2: 46 percent / NaOEt / ethanol / 4 h / Heating

With sodium ethanolate; trichlorophosphate; In ethanol;

DOI:10.1021/jm00183a012

upstream raw materials:

urea

(E)-3-(dimethylamino)-2-(meta-tolyloxy)acrylaldehyde

3-methylphenoxyacetaldehyde diethyl acetal

3-methyl-phenol

Refernces

• 1、 -. "METHOD FOR PREPARING TOLIMIDONE ON LARGE SCALE". . . Retrieved 2018/04/13.