1227484-18-5

Basic information

• Product Name: 5-bromo-2-hydroxy-4-(methoxymethoxy)benzaldehyde
• Synonyms: 5-bromo-2-hydroxy-4-(methoxymethoxy)benzaldehyde
• CAS NO: 1227484-18-5
• Molecular Weight: 261.072
• Mol File: 1227484-18-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5-bromo-2-hydroxy-4-(methoxymethoxy)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-hydroxy-4-(methoxymethoxy)benzaldehyde(1227484-18-5)
• EPA Substance Registry System: 5-bromo-2-hydroxy-4-(methoxymethoxy)benzaldehyde(1227484-18-5)

Safety Data

• Hazardous Substances Data: 1227484-18-5(Hazardous Substances Data)

Upstream product

• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 116096-90-3 5-bromo-2,4-dihydroxy-benzaldehyde 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 1227484-24-3 5-bromo-2-methoxy-4-(methoxymethoxy)benzaldehyde 
• 1257999-33-9 5-bromo-4-methoxymethoxy-2-[4-(trifluoromethyl)benzyloxy]benzaldehyde 
• 1257999-37-3 2-[3,5-bis(trifluoromethyl)benzyloxy]-5-bromo-4-(methoxymethoxy)benzaldehyde 
• 1620146-74-8 5-bromo-4-butoxy-2-methoxybenzaldehyde 
• 1620146-75-9 4-(benzyloxy)-5-bromo-2-methoxybenzaldehyde 
• 1620146-39-5 (Z)-5-(5-bromo-4-hydroxy-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-40-8 (Z)-5-(5-bromo-2, 4-dimethoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-41-9 (Z)-5-(5-bromo-4-(allyloxy)-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-42-0 (Z)-5-(5-bromo-4-((3-methylbut-2-en-1-yl)oxy)-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-43-1 (Z)-5-(5-bromo-4-butoxy-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-44-2 (Z)-5-(5-bromo-4-benzyloxy-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-45-3 (Z)-5-(5-bromo-2, 4-dimethoxybenzylidene)-3-methylthiazolidine-2,4-dione 
• 1620146-46-4 (Z)-5-(5-bromo-4-benzyloxy-2-methoxybenzylidene)-3-methylthiazolidine-2,4-dione 
• 1620146-47-5 (Z)-5-(5-bromo-2-methoxy-4-((3-methylbut-2-en-1-yl)oxy)benzylidene)-3-methylthiazolidine-2,4-dione 

Relevant articles and documents

Synthetic route of compound and application thereof in field of preparation of anti-diabetic drugs

The invention belongs to the technical field of drug synthesis, and particularly relates to a synthetic route of a compound and application of the compound in the field of preparation of anti-diabeticdrugs. The invention provides a synthetic route of SN158, and also provides the application of the synthetic route in the field of preparation of anti-diabetic drugs. The synthetic route of the invention comprises the following steps: brominating a raw material, namely 2,4-dihydroxybenzaldehyde; protecting para-hydroxyl groups by using methoxymethyl groups; methylating ortho-hydroxyl groups by using dimethyl sulfate or methyl iodide; and carrying out a Claisen-Schmidt condensation reaction by using a hydrochloric acid ethanol or boron trifluoride diethyl ether solution, with HATU or EDCI andHOBt as coupling agents for an amidation reaction. According to the invention, the yield of the prepared SN158 can reach 60% or above; meanwhile, column chromatographic purification is not needed in the preparation process, and the finally produced compound with a purity of 99% or above can be obtained only through recrystallization; and the method is suitable for large-scale/industrial productionand overcomes the technical defects that SN158 is low in synthesis yield and complex in purification in the prior art.

Design, synthesis and docking study of 5-(substituted benzylidene) thiazolidine-2,4-dione derivatives as inhibitors of protein tyrosine phosphatase 1B

A series of novel 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives was designed, and synthesized based on our previous studies. Also their activities were evaluated as competitive inhibitors of protein tyrosine phosphatase 1B (PTP1B). Compounds 6d-6g, 7b, 7c, 7e, 7j, 7k, 7m, 14b and 14e-14f showed potent inhibitory effects against PTP1B, and compound 7e, the most potent among the series, had an IC50 of 4.6 μM. Also a Surflex-Dock docking model of 7e was studied. Compound 7e showed a negative binding energy of -7.35 kcal/mol and a high affinity to PTP1B residues (Gly220, Ala217, Arg221, Asp181, Ser216, Cys215, Phe182, Gln262 and Ile219) in the active sites, indicating that it may stabilize the open form and generate tighter binding to the catalytic sites of PTP1B.

Novel thiazolidinedione derivatives with anti-obesity effects: Dual action as PTP1B inhibitors and PPAR-γ activators

Benzylidene-2,4-thiazolidinedione derivatives with substitutions at both the ortho and para-positions of the phenyl group were synthesized as PTP1B inhibitors with IC50 values in a low micromolar range. Compound 18l, the lowest, bore an IC50 of 1.3 μM. In a peroxisome proliferator-activated receptor-γ (PPAR-γ) promoter reporter gene assay, 18l was found to activate the transcription of the reporter gene with potencies comparable to those of troglitazone, rosiglitazone, and pioglitazone. In vivo efficacy of 18l as an anti-obesity and hypoglycemic agent was evaluated in a mouse model system. Compound 18l significantly suppressed weight gain and significantly improved blood parameters such as TG, total cholesterol and NEFA without overt toxic effects.