Production Method 1

1035229-31-2

871101-87-0

Reaction Conditions

1.1 Catalysts: Zinc Solvents: Acetic acid ;  15 min, rt; rt → 40 °C; 2 h, 40 °C → rt

Reference

Discovery of A-893, A New Cell-Active Benzoxazinone Inhibitor of Lysine Methyltransferase SMYD2

Sweis, Ramzi F.; et al, ACS Medicinal Chemistry Letters, 2015, 6(6), 695-700

Production Method 2

89684-58-2

871101-87-0

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Solvents: Dimethylformamide ;  10 min, rt
1.2 20 h, rt
1.3 Reagents: Water ;  cooled
2.1 Reagents: Zinc Solvents: Acetic acid ;  rt; 2 h, rt

Reference

Synthesis of β2-AR agonist BI-167107

Wang, Jiangbo; et al, Youji Huaxue, 2013, 33(3), 634-639

Production Method 3

1035229-31-2

871101-87-0

Reaction Conditions

1.1 Reagents: Zinc Solvents: Acetic acid ;  rt; 2 h, rt

Reference

Synthesis of β2-AR agonist BI-167107

Wang, Jiangbo; et al, Youji Huaxue, 2013, 33(3), 634-639

Production Method 4

89684-58-2

871101-87-0

Reaction Conditions

1.1 Reagents: Sodium bicarbonate Solvents: Acetonitrile ;  rt → 60 °C; 6.5 h, 60 °C → reflux
1.2 Solvents: tert-Butyl methyl ether ,  Water ;  reflux → 60 °C; 60 °C → 45 °C; 1.5 h, 45 °C → 20 °C
2.1 Catalysts: Zinc Solvents: Acetic acid ;  15 min, rt; rt → 40 °C; 2 h, 40 °C → rt

Reference

Discovery of A-893, A New Cell-Active Benzoxazinone Inhibitor of Lysine Methyltransferase SMYD2

Sweis, Ramzi F.; et al, ACS Medicinal Chemistry Letters, 2015, 6(6), 695-700

Production Method 5

601-89-8

871101-87-0

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Nitrobenzene ;  15 min, rt
1.2 Solvents: Acetic anhydride ;  15 min; 5 h, rt → 100 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  cooled
2.1 Reagents: Sodium bicarbonate Solvents: Acetonitrile ;  rt → 60 °C; 6.5 h, 60 °C → reflux
2.2 Solvents: tert-Butyl methyl ether ,  Water ;  reflux → 60 °C; 60 °C → 45 °C; 1.5 h, 45 °C → 20 °C
3.1 Catalysts: Zinc Solvents: Acetic acid ;  15 min, rt; rt → 40 °C; 2 h, 40 °C → rt

Reference

Discovery of A-893, A New Cell-Active Benzoxazinone Inhibitor of Lysine Methyltransferase SMYD2

Sweis, Ramzi F.; et al, ACS Medicinal Chemistry Letters, 2015, 6(6), 695-700

Production Method 6

601-89-8

871101-87-0

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Nitrobenzene ;  rt; 5 h, 100 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  cooled
2.1 Reagents: Lithium tert-butoxide Solvents: Dimethylformamide ;  10 min, rt
2.2 20 h, rt
2.3 Reagents: Water ;  cooled
3.1 Reagents: Zinc Solvents: Acetic acid ;  rt; 2 h, rt

Reference

Synthesis of β2-AR agonist BI-167107

Wang, Jiangbo; et al, Youji Huaxue, 2013, 33(3), 634-639

1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one Raw materials

• 1-(2,4-dihydroxy-3-nitro-phenyl)ethanone
• Nitroresorcinol
• 1-(4-benzyloxy-2-hydroxy-3-nitro-phenyl)ethanone

1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one Preparation Products

• 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one (871101-87-0)

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• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

Professional Introduction to 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one (CAS No. 871101-87-0)

1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one is a sophisticated organic compound that has garnered significant attention in the field of pharmaceutical chemistry and bioorganic synthesis. This compound, identified by its CAS number 871101-87-0, exhibits a unique structural framework that positions it as a potential candidate for various applications in medicinal chemistry and drug discovery. The presence of multiple functional groups, including an amino group, a benzyloxy group, and a hydroxyl group, contributes to its versatile reactivity and makes it an intriguing subject for further exploration.

The structural motif of 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one is characterized by a phenyl ring substituted with these distinct functional groups. The amino group at the 3-position and the hydroxyl group at the 2-position introduce basic and acidic properties, respectively, while the benzyloxy group at the 4-position enhances lipophilicity and stability. This combination of features makes the compound a promising scaffold for designing molecules with tailored biological activities.

In recent years, there has been growing interest in developing novel therapeutic agents that target complex biological pathways. The compound 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one has been investigated for its potential role in modulating various pharmacological targets. For instance, studies have suggested that this molecule may interact with enzymes and receptors involved in inflammation, pain perception, and neurodegenerative diseases. The precise arrangement of functional groups in its structure allows for selective binding to biological targets, making it a valuable asset in rational drug design.

The benzyloxy group in 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one plays a crucial role in determining its pharmacokinetic properties. This moiety enhances the compound's solubility and bioavailability, which are critical factors for drug efficacy. Additionally, the benzyloxy group can participate in hydrogen bonding interactions with biological targets, further improving binding affinity. These characteristics make the compound an attractive candidate for further development into a lead compound for new drugs.

Recent advancements in computational chemistry have enabled researchers to predict the biological activity of molecules with high accuracy. Molecular docking studies have been performed on 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one to identify potential binding sites on target proteins. These studies have revealed that the compound can interact with enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), which are key players in inflammatory processes. The ability to modulate these enzymes could lead to the development of novel anti-inflammatory therapies.

In addition to its potential applications in inflammation research, 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one has also been explored for its neuroprotective properties. Preclinical studies have indicated that this compound may protect against oxidative stress and neurotoxicity, making it a promising candidate for treating neurodegenerative diseases such as Alzheimer's and Parkinson's disease. The hydroxyl group at the 2-position of its structure is believed to contribute to these protective effects by scavenging reactive oxygen species.

The synthesis of 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one presents an interesting challenge due to its complex structural features. Researchers have developed multi-step synthetic routes that involve functional group transformations such as nucleophilic substitution, condensation reactions, and oxidation processes. These synthetic strategies highlight the compound's synthetic utility and demonstrate its feasibility for large-scale production if needed.

The future prospects of 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one in pharmaceutical research are promising. Ongoing studies aim to optimize its chemical structure to enhance its biological activity and reduce potential side effects. By leveraging modern techniques such as high-throughput screening and structure-based drug design, researchers hope to identify derivatives of this compound that exhibit improved therapeutic profiles.

In conclusion, 1-[3-amino-4-(benzyloxy)-2-hydroxyphenyl]ethan-1-one, identified by its CAS number 871101-87-0, is a structurally unique organic compound with significant potential in pharmaceutical applications. Its versatile functional groups and favorable pharmacokinetic properties make it an attractive scaffold for drug discovery. With continued research and development, this compound holds promise for contributing to advancements in medicine and improving human health.

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