912545-10-9

Basic information

• Product Name: 2,4-bis(benzyloxy)-5-bromobenzoic acid
• Synonyms: 2,4-bis(benzyloxy)-5-bromobenzoic acid
• CAS NO: 912545-10-9
• Molecular Formula: C₂₁H₁₇BrO₄
• Molecular Weight: 413.26128
• Mol File: 912545-10-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 553.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.437±0.06 g/cm3(Predicted)
• PKA: 3.36±0.36(Predicted)
• CAS DataBase Reference: 2,4-bis(benzyloxy)-5-bromobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-bis(benzyloxy)-5-bromobenzoic acid(912545-10-9)
• EPA Substance Registry System: 2,4-bis(benzyloxy)-5-bromobenzoic acid(912545-10-9)

Safety Data

• Hazardous Substances Data: 912545-10-9(Hazardous Substances Data)

Usage

General Description

2,4-bis(benzyloxy)-5-bromobenzoic acid is a chemical compound with the molecular formula C21H17BrO4. It is a white or off-white powder that is insoluble in water and soluble in organic solvents. 2,4-bis(benzyloxy)-5-bromobenzoic acid is used in organic synthesis and as a building block for the preparation of various pharmaceuticals and agrochemicals. It is also used as an intermediate in the production of dyes and pigments. The presence of the bromine atom makes this compound reactive in a variety of chemical reactions, making it a versatile building block for the synthesis of complex organic molecules.

Upstream product

• 912545-14-3 benzyl 2,4-bis(benzyloxy)-5-bromobenzoate 
• 7355-22-8 5-bromo-4-hydroxysalicylic acid 
• 100-39-0 benzyl bromide 
• 958253-44-6 methyl 2,4-bis(benzyloxy)-5-bromobenzoate 
• 89-86-1 4-hydroxysalicylic acid 
• 98437-43-5 methyl 2-chloro-3,4-dihydroxybenzoate 

Downstream Products

• 898538-48-2 2,4-bis-benzyloxy-5-bromo-benzyl alcohol 
• 1143623-80-6 2,4-bis-benzyloxy-5-bromo-N-(3-methoxypropyl)benzamide 
• 958253-46-8 2,4-bisbenzyloxy-5-bromobenzoyl chloride 
• 913000-15-4 (2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone 
• 1609699-84-4 (2,4-dihydroxy-5-(phenylamino)phenyl)(isoindolin-2-yl)methanone 
• 1609699-85-5 (2,4-dihydroxy-5-(p-tolylamino)phenyl)(isoindolin-2-yl)methanone 
• 1609699-86-6 (5-((2,4-dichlorophenyl)amino)-2,4-dihydroxyphenyl)(isoindolin-2-yl)methanone 
• 1609699-97-9 (2,4-bis(benzyloxy)-5-(1H-pyrrolo[3,2-b]pyridin-1-yl)phenyl)(isoindolin-2-yl)methanone 
• 1609699-98-0 (2,4-bis(benzyloxy)-5-(1H-pyrrolo[3,2-c]pyridin-1-yl)phenyl)(isoindolin-2-yl)methanone 
• 1609699-63-9 N-(2-(1-(2,4-bis(benzyloxy)-5-(isoindoline-2-carbonyl)phenyl)-5-methoxy-1H-indol-3-yl)ethyl)acetamide 
• 1609699-64-0 (5-(3-(2-aminoethyl)-5-methoxy-1H-indol-1-yl)-2,4-bis(benzyloxy)phenyl)(isoindolin-2-yl)methanone 
• 1609699-65-1 methyl 2-(1-(2,4-bis(benzyloxy)-5-(isoindoline-2-carbonyl)phenyl)-1H-indol-3-yl)acetate 
• 1609699-66-2 (2,4-bis(benzyloxy)-5-(4-bromo-1H-indol-1-yl)phenyl)(isoindolin-2-yl)methanone 
• 1609699-67-3 (2,4-bis(benzyloxy)-5-(4-nitro-1H-indol-1-yl)phenyl)(isoindolin-2-yl)methanone 

Relevant articles and documents

Novel Tetrahydropyrido[4,3-d]pyrimidines as Potent Inhibitors of Chaperone Heat Shock Protein 90

Heat shock protein 90 (Hsp90) is a potential target for oncology therapeutics. Some inhibitors have shown antitumor effects in clinical trials, spurring the discovery of small molecule Hsp90 inhibitors. Here, we describe the structural optimization studies of a hit compound, tetrahydropyrido[4,3-d]pyrimidine-based Hsp90 inhibitor 15, which exhibits inhibitory activity against Hsp90. A series of analogues were synthesized, and their structure-activity and structure-property relationships were analyzed. These explorations led to the discovery of compound 73, which exhibited potent in vitro activities, good physicochemical properties, favorable ADME properties, and a potent antitumor effect in an HCT116 xenograft model. Furthermore, 73 exhibited no ocular toxicity in a rat retinal damage model, suggesting it is a relatively safe Hsp90 inhibitor. As a promising antitumor agent, 73 was progressed for further preclinical evaluation.

TRIAZOLE DERIVATIVE AS AN HSP 90 INHIBITOR

5-[4-(2-Methylphenyl)-3-hydroxy-4H-1,2,4-triazol-5-yl]-2,4-dihydroxy-N-methyl-N-butylbenzamide is an HSP90 inhibitor and can be used for the preparation of a medicament for the treatment of diseases in which the inhibition, regulation and/or modulation of HSP90 plays a role.

Discovery of (2,4-Dihydroxy-5-isopropylphenyl)-[5-(4-methylpiperazin-1- ylmethyl)-1,3-dihydroisoindol-2-yl]methanone (AT13387), a novel inhibitor of the molecular chaperone Hsp90 by fragment based drug design

Inhibitors of the molecular chaperone heat shock protein 90 (Hsp90) are currently generating significant interest in clinical development as potential treatments for cancer. In a preceding publication (DOI: 10.1021/jm100059d) we describe Astex's approach to screening fragments against Hsp90 and the subsequent optimization of two hits into leads with inhibitory activities in the low nanomolar range. This paper describes the structure guided optimization of the 2,4-dihydroxybenzamide lead molecule 1 and details some of the drug discovery strategies employed in the identification of AT13387 (35), which has progressed through preclinical development and is currently being tested in man.