Production Method 1

121-33-5

88449-50-7

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  20 °C
1.2 Reagents: Potassium borohydride Solvents: Methanol ;  20 °C
1.3 Reagents: Thionyl chloride Solvents: Dichloromethane ;  0 °C
1.4 Solvents: Acetonitrile ;  reflux
1.5 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  reflux

Reference

Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents

Shen, Li; et al, European Journal of Medicinal Chemistry, 2014, 85, 807-817

Production Method 2

861069-45-6

88449-50-7

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  reflux

Reference

Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents

Shen, Li; et al, European Journal of Medicinal Chemistry, 2014, 85, 807-817

Production Method 3

306-08-1

88449-50-7

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt; 24 h, reflux
2.1 Reagents: Lithium hydroxide Solvents: Tetrahydrofuran ,  Water ;  24 h, reflux
2.2 Solvents: Diethyl ether ;  reflux → 0 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, 0 °C

Reference

Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach

Dittrich, Nora; et al, Tetrahedron, 2017, 73(14), 1881-1894

Production Method 4

498-00-0

88449-50-7

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  24 h, 120 °C; 120 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 10, rt
1.3 Reagents: Acetic acid Solvents: Water ;  pH 7, rt
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  2 d, 80 °C
3.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt; 24 h, reflux
4.1 Reagents: Lithium hydroxide Solvents: Tetrahydrofuran ,  Water ;  24 h, reflux
4.2 Solvents: Diethyl ether ;  reflux → 0 °C
4.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, 0 °C

Reference

Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach

Dittrich, Nora; et al, Tetrahedron, 2017, 73(14), 1881-1894

Production Method 5

121-33-5

88449-50-7

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  20 °C
2.1 Reagents: Potassium borohydride Solvents: Methanol ;  20 °C
3.1 Reagents: Thionyl chloride Solvents: Dichloromethane ;  0 °C
4.1 Solvents: Acetonitrile ;  reflux
5.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  reflux

Reference

Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents

Shen, Li; et al, European Journal of Medicinal Chemistry, 2014, 85, 807-817

Production Method 6

1256581-67-5

88449-50-7

Reaction Conditions

1.1 Reagents: Lithium hydroxide Solvents: Tetrahydrofuran ,  Water ;  24 h, reflux
1.2 Solvents: Diethyl ether ;  reflux → 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, 0 °C

Reference

Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach

Dittrich, Nora; et al, Tetrahedron, 2017, 73(14), 1881-1894

Production Method 7

2538-98-9

88449-50-7

Reaction Conditions

1.1 Reagents: Potassium borohydride Solvents: Methanol ;  rt
1.2 Reagents: Thionyl chloride Solvents: Dichloromethane ;  0 °C
1.3 Solvents: Acetonitrile ;  reflux
1.4 Reagents: Potassium hydroxide Solvents: Ethanol ;  reflux

Reference

Novel hybrids from lamellarin D and combretastatin A4 as cytotoxic agents

Shen, Li; et al, European Journal of Medicinal Chemistry, 2010, 45(1), 11-18

Production Method 8

1036588-32-5

88449-50-7

Reaction Conditions

1.1 Solvents: Acetonitrile ;  reflux
2.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  reflux

Reference

Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents

Shen, Li; et al, European Journal of Medicinal Chemistry, 2014, 85, 807-817

Production Method 9

2539-22-2

88449-50-7

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dichloromethane ;  0 °C
2.1 Solvents: Acetonitrile ;  reflux
3.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  reflux

Reference

Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents

Shen, Li; et al, European Journal of Medicinal Chemistry, 2014, 85, 807-817

Production Method 10

4468-59-1

88449-50-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  2 d, 80 °C
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt; 24 h, reflux
3.1 Reagents: Lithium hydroxide Solvents: Tetrahydrofuran ,  Water ;  24 h, reflux
3.2 Solvents: Diethyl ether ;  reflux → 0 °C
3.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, 0 °C

Reference

Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach

Dittrich, Nora; et al, Tetrahedron, 2017, 73(14), 1881-1894

Production Method 11

2538-98-9

88449-50-7

Reaction Conditions

1.1 Reagents: Potassium borohydride Solvents: Methanol ;  20 °C
2.1 Reagents: Thionyl chloride Solvents: Dichloromethane ;  0 °C
3.1 Solvents: Acetonitrile ;  reflux
4.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  reflux

Reference

Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents

Shen, Li; et al, European Journal of Medicinal Chemistry, 2014, 85, 807-817

Production Method 12

121-33-5

88449-50-7

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  30 min, 0 °C; 0 °C → rt; 24 h, rt
2.1 Solvents: Dimethylformamide ;  24 h, 120 °C; 120 °C → rt
2.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 10, rt
2.3 Reagents: Acetic acid Solvents: Water ;  pH 7, rt
3.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  2 d, 80 °C
4.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt; 24 h, reflux
5.1 Reagents: Lithium hydroxide Solvents: Tetrahydrofuran ,  Water ;  24 h, reflux
5.2 Solvents: Diethyl ether ;  reflux → 0 °C
5.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, 0 °C

Reference

Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach

Dittrich, Nora; et al, Tetrahedron, 2017, 73(14), 1881-1894

3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid Raw materials

• Isopropyl 2-(4-isopropoxy-3-methoxyphenyl)acetate
• 4-Isopropoxy-3-methoxybenzyl chloride
• (4-Hydroxy-3-methoxyphenyl)acetonitrile
• 2-(4-Isopropoxy-3-methoxyphenyl)acetonitrile
• Vanillin
• 4-Isopropoxy-3-methoxy-benzyl alcohol
• Vanillyl alcohol
• 4-Hydroxy-3-methoxyphenylacetic Acid
• 3-methoxy-4-(propan-2-yloxy)benzaldehyde

3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid Preparation Products

• 3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid (88449-50-7)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers Anisoles

Recent Advances in the Study of 3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid (CAS: 88449-50-7)

3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid (CAS: 88449-50-7) is a chemical compound of significant interest in the field of chemical biology and pharmaceutical research. This compound, characterized by its unique methoxy and isopropoxy substituents on the benzene ring, has been the subject of recent studies due to its potential therapeutic applications. The latest research has focused on its synthesis, pharmacological properties, and mechanisms of action, providing valuable insights for drug development and biomedical applications.

Recent studies have explored the synthetic pathways for 3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid, with an emphasis on optimizing yield and purity. Advanced techniques such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy have been employed to characterize the compound and ensure its structural integrity. These methodological advancements have facilitated a deeper understanding of the compound's chemical behavior and stability under various conditions.

Pharmacological investigations have revealed that 3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid exhibits notable anti-inflammatory and analgesic properties. In vitro and in vivo studies have demonstrated its ability to modulate key inflammatory pathways, including the inhibition of cyclooxygenase (COX) enzymes. These findings suggest potential applications in the treatment of chronic inflammatory diseases, such as rheumatoid arthritis and osteoarthritis, positioning the compound as a promising candidate for further drug development.

Moreover, recent research has highlighted the compound's potential role in oncology. Preliminary studies indicate that 3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid may possess anti-proliferative effects against certain cancer cell lines. Mechanistic studies are underway to elucidate its interactions with cellular targets and pathways involved in tumor growth and metastasis. These discoveries open new avenues for exploring its utility in cancer therapy, either as a standalone agent or in combination with existing treatments.

In addition to its therapeutic potential, the safety profile of 3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid has been a focal point of recent investigations. Toxicological assessments have shown favorable results, with minimal adverse effects observed in preclinical models. These findings underscore the compound's suitability for further clinical evaluation, although comprehensive pharmacokinetic and pharmacodynamic studies are still needed to fully assess its efficacy and safety in humans.

In conclusion, the latest research on 3-Methoxy-4-(1-methylethoxy)-benzeneacetic Acid (CAS: 88449-50-7) underscores its multifaceted potential in chemical biology and pharmaceutical applications. From its optimized synthesis to its promising pharmacological properties, this compound represents a valuable area of study for researchers aiming to develop novel therapeutic agents. Future studies should focus on advancing its clinical translation and exploring its mechanisms of action in greater detail.

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