1476847-52-5

Basic information

• Product Name: 1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone
• Synonyms: 1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone;1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethan-1-one;EOS-61406
• CAS NO: 1476847-52-5
• Molecular Formula: C₁₈H₁₅BrO₄
• Molecular Weight: 375.2133
• Mol File: 1476847-52-5.mol

Chemical Properties

• Boiling Point: 488.8±40.0 °C(Predicted)
• Appearance: /
• Density: 1.444±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone(1476847-52-5)
• EPA Substance Registry System: 1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone(1476847-52-5)

Safety Data

• Hazardous Substances Data: 1476847-52-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone is utilized as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its unique structure allows for multiple points of reactivity, making it a valuable building block in the synthesis of pharmaceuticals and other specialty chemicals.
Used in Drug Discovery Research:
In the pharmaceutical industry, 1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone is employed as a lead compound in drug discovery. Its potential pharmacological properties are being explored for the development of new therapeutic agents. 1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone's structural diversity and the presence of bioisosteric groups make it a promising candidate for medicinal chemistry optimization.
Used in Chemical Research:
1-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoethanone is also used in academic and industrial chemical research to study the reactivity and properties of complex organic molecules. Its unique structure provides opportunities for investigating novel reaction mechanisms and the synthesis of new chemical entities with potential applications in various fields.

Upstream product

• 100-39-0 benzyl bromide 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 83-30-7 acide 2,4,6-trihydroxybenzoique 
• 137571-73-4 5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 108-73-6 3,5-dihydroxyphenol 
• 1132988-93-2 2-hydroxy-4,6-bis(methoxymethoxy)benzaldehyde 
• 1476847-51-4 1-[4-(benzyloxy)-6-methoxy-1-benzofuran-2-yl]ethan-1-one 
• 1476847-50-3 2-(benzyloxy)-6-hydroxy-4-methoxybenzaldehyde 
• 532394-23-3 5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one 
• 1476847-49-0 5-(benzyloxy)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3 ]dioxin-4-one 

Downstream Products

• 1476848-33-5 2-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-6-methylimidazo[1,2-b]pyridazine 
• 1476848-37-9 (S)-6-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-(1-fluoroethyl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1476847-68-3 2-Methoxy-6-(6-methoxy-4-((5-phenyl-1,3,4-thiadiazol-2-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1476847-69-4 2-Methoxy-6-(6-methoxy-4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1476847-71-8 2-Methoxy-6-(6-methoxy-4-((1-phenyl-1H-1,2,3-triazol-5-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1476848-32-4 4-(((6-Methoxy-2-(6-methylimidazo[1,2-b]pyridazin-2-yl)benzofuran-4-yl)oxy)methyl)-2-phenylthiazole 
• 1476848-35-7 (S)-2-(1-Fluoroethyl)-6-(6-methoxy-4-((2-phenylthiazol-4-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1476847-55-8 6-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-methoxyimidazo[2,1-b][1,3,4]thiadiazole 
• 1476847-58-1 (4-(4-(((6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzofuran-4-yl)oxy)methyl)-5-methylthiazol-2-yl)morpholine) 
• 1476847-59-2 2-Methoxy-6-(6-methoxy-4-((4-phenylthiazol-2-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1476847-51-4 1-[4-(benzyloxy)-6-methoxy-1-benzofuran-2-yl]ethan-1-one 
• 1476847-54-7 6-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-bromoimidazo[2,1-b][1,3,4]thiadiazole 

Relevant articles and documents

Synthesis and evaluation of novel and potent protease activated receptor 4 (PAR4) antagonists based on a quinazolin-4(3H)-one scaffold

Protease activated receptor 4 (PAR4) is an important target in antiplatelet therapy to reduce the risk of heart attack and thrombotic complications in stroke. PAR4 antagonists can prevent harmful and stable thrombus growth, while retaining initial thrombus formation, by acting on the late diffusion stage of platelet aggregation, and may provide a safer alternative to other antiplatelet agents. To date, only two PAR4 antagonists, BMS-986120 and BMS-986141 have entered clinical trials for thrombosis. Thus, the development of a potent and selective PAR4 antagonist with a novel chemotype is highly desirable. In this study, we explored the activity of quinazolin-4(3H)-one-based PAR4 antagonists, beginning with their IDT analogues. By repeated structural optimisation, we developed a series of highly selective PAR4 antagonists with nanomolar potency on human platelets. Of these, 13 and 30g, with an 8-benzo[d]thiazol-2-yl-substituted quinazolin-4(3H)-one structure, showed optimal activity (h. PAR4-AP PRP IC50 = 19.6 nM and 6.59 nM, respectively) on human platelets. Furthermore, 13 and 30g showed excellent selectivity for PAR4 versus PAR1 and other receptors (IC50s > 10 μM) on human platelets. And 13 and 30g were lack of cross-reactivity for PAR1 or PAR2 (PAR1 AP FLIPR IC50 > 3162 nM, PAR2 AP FLIPR IC50 > 1000 nM) in the calcium mobilization assays. Metabolic stability assays and cytotoxicity tests of 13 and 30g indicated that these compounds could sever as promising drug candidates for the development of novel PAR4 antagonists. In summary, the quinazolin-4(3H)-one-based analogues are the first reported chemotypes with excellent activity and selectivity against PAR4, and, in the current study, we expanded the structural diversity of PAR4 antagonists. The two compounds, 13 and 30g, found in our study could be promising starting points with great potential for further research in antiplatelet therapy.

Discovery of Potent Protease-Activated Receptor 4 Antagonists with in Vivo Antithrombotic Efficacy

In an effort to identify novel antithrombotics, we have investigated protease-activated receptor 4 (PAR4) antagonism by developing and evaluating a tool compound, UDM-001651, in a monkey thrombosis model. Beginning with a high-throughput screening hit, we identified an imidazothiadiazole-based PAR4 antagonist chemotype. Detailed structure-activity relationship studies enabled optimization to a potent, selective, and orally bioavailable PAR4 antagonist, UDM-001651. UDM-001651 was evaluated in a monkey thrombosis model and shown to have robust antithrombotic efficacy and no prolongation of kidney bleeding time. This combination of excellent efficacy and safety margin strongly validates PAR4 antagonism as a promising antithrombotic mechanism.

Benzofuran derivatives, preparation method thereof and application of the derivatives in medicine

The invention relates to benzofuran derivatives, a preparation method thereof and application of the derivatives in medicine, particularly novel benzofuran derivatives shown as a general formula (I),a preparation method thereof, pharmaceutical compositions comprising the derivatives and application thereof as therapeutic agent, especially as PAR-4 antagonists, with substitutes in the general formula (I) being defined in the description.

Synthesis and biological evaluation of BMS-986120 and its deuterated derivatives as PAR4 antagonists

BMS-986120 is a PAR4 antagonist that is being investigated as an antiplatelet agent in phase I clinical trial. An improved synthesis of BMS-986120 has been developed. Based on the novel synthetic approach to BMS-986120, a series of deuterated derivatives of BMS-986120 have been synthesized and biologically evaluated to search for more potent antiplatelet agents. The in vitro antiplatelet assay by turbidimetry demonstrated that PC-2 and PC-6 had IC50 values of 6.30 nM and 6.97 nM, respectively, versus BMS-986120 with an IC50 of 7.80 nM. The result of in vitro metabolic stability study showed that all of the deuterated compounds had similar half-life (T1/2) and intrinsic clearance (Clint) in comparison with BMS-986120. Further probing the metabolic profile of BMS-986120 is worth being conducted.

HETEROCYCLIC COMPOUNDS AS INHIBITORS OF PLATELET AGGREGATION

The present invention provides compounds of Formula I: wherein Y, AA, W, R3, R2, R4, R5, R6, R7, X1, X2, X3, X4 and X5 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug or esters or solvate form thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of platelet aggregation and thus can be used as medicaments for treating or preventing thromboembolic disorders.

PAR4 AGONIST PEPTIDES

The present invention provides PAR4 agonist peptides. These peptides are useful for developing robust PAR4 receptor assays.

IMIDAZOTHIADIAZOLE AND IMIDAZOPYRIDAZINE DERIVATIVES AS PROTEASE ACTIVATED RECEPTOR 4 (PAR4) INHIBITORS FOR TREATING PLATELET AGGREGATION

The present invention provides imidazothiadiazole compounds of Formula (I); Wherein W,Y, R0, R2, R4, Ra, Rb, X1, X2, X3 and X4 are as defined herein,, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of platelet aggregation and thus can be used as medicaments for treating or preventing thromboembolic disorders.

IMIDAZOTHIADIAZOLE AND IMIDAZOPYRAZINE DERIVATIVES AS PROTEASE ACTIVATED RECEPTOR 4 (PAR4) INHIBITORS FOR TREATING PLATELET AGGREGATION

The present invention provides thiazole compounds of Formula I wherein W, Y, R0, R2, R4, R5, R6, R7, X1, X2, X3 and X4 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of platelet aggregation and thus can be used as medicaments for treating or preventing thromboembolic disorders.

IMIDAZOTHIADIAZOLE DERIVATIVES AS PROTEASE ACTIVATED RECEPTOR 4 (PAR4) INHIBITORS FOR TREATING PLATELET AGGREGATION

The present invention provides imidazothiadiazole compounds of Formula (I) wherein A, B, D, Rx, R1, R2, R3, X1, X2 and s are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt or solvate form thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of platelet aggregation and thus can be used as medicaments.