DMOG

Base Information

• Chemical Name: DMOG
• CAS No.: 89464-63-1
• Molecular Formula: C6H9 N O5
• Molecular Weight: 175.141
• Hs Code.: 2924199090
• Mol file: 89464-63-1.mol

Synonyms:Glycine,N-(methoxyoxoacetyl)-, methyl ester (9CI); Oxamic acid, (carboxymethyl)-,dimethyl ester (7CI); 2: PN: US6833489 FIGURE: 1 claimed sequence;N-[(Methoxycarbonyl)methyl]oxamic acid methyl ester

Chemical Property of DMOG

Chemical Property:

• Melting Point: 46-48°C
• Boiling Point: 179-182 °C(Press: 12 Torr)
• PKA: 10.55±0.46(Predicted)
• PSA: 81.70000
• Density: 1.247g/cm3
• LogP: -1.16050
• Storage Temp.: Refrigerator
• Solubility.: H2O: >30mg/mL
• Water Solubility.: Soluble in water at 30mg/ml.

Purity/Quality:

99% ^*data from raw suppliers

DMOG ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: The pro-angiogenic factor HIF-1α is targeted for destruction in normoxic environments by the hydroxylation of a specific proline residue, P564, by the oxygen-sensing enzyme HIF-1α prolyl hydroxylase (HIF-PH). DMOG is a cell permeable, competitive inhibitor of HIF-PH. It acts to stabilize HIF-1α expression at normal oxygen tensions in cultured cells, at concentrations between 0.1 and 1 mM. DMOG is therefore expected to act as a pro-angiogenic compound, acting via the HIF-1α system.
• Uses: DMOG is a cell permeable prolyl-4-hydroxylase inhibitor which upregulates HIF activity. HIF activation stimulates angiogenesis in several different models (1nM). DMOG also inhibits FIH (factor inhibiting HIF), an asparaginyl hydroxylase, which enhances the HIF response. It is active in vivo and attenuates myocardial injury in a rabbit ischemia reperfusion model (20mg/Kg). DMOG is a cell permeable prolyl-4-hydroxylase inhibitor that regulates hypoxia-inducible factor

Technology Process of DMOG

There total 4 articles about DMOG 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: 100.0%

Dimethyl oxalate (553-90-2) + glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) → dimethyloxalylglycine (89464-63-1)

Guidance literature:

With triethylamine; In methanol;

Reference yield: 87.0%

monomethyl oxalyl chloride (5781-53-3) + glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) → dimethyloxalylglycine (89464-63-1)

Guidance literature:

With triethylamine; In toluene; for 5h; Reflux;

DOI:10.1016/j.tetlet.2008.12.080

Reference yield:

dimethyl iminodiacetate (6096-81-7) → dimethyloxalylglycine (89464-63-1) + methyl 2-amino-2-oxoacetate (62155-27-5)

Guidance literature:

With oxygen; fullerene-C₆₀; [5,6]fullerene-C₇₀; In toluene; at 60 ℃; Irradiation;

DOI:10.1021/jo015749m

upstream raw materials:

monomethyl oxalyl chloride

glycine ethyl ester hydrochloride

dimethyl iminodiacetate

Dimethyl oxalate

Downstream raw materials:

methyl 5-methoxy-1,3-oxazole-2-carboxylate

Refernces

• 1、 -. "PYRAZOLE DERIVATIVE". Page/Page column 66. . Retrieved 2010/11/27.
• 2、 -. "HIV INTEGRASE INHIBITORS". Page/Page column 25-26. . Retrieved 2008/06/13.