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3-amino-3-arylpropionic acid and preparation method thereof

A technology of aryl propionic acid and amino, applied in the field of 3-amino-3-aryl propionic acid and its preparation, achieving the effects of simple method, high yield and easy availability of raw materials

Active Publication Date: 2011-03-02
合肥华纳生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For pharmaceutical companies, no one dares to ignore the role of unnatural amino acids in the development of new drugs

Method used

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  • 3-amino-3-arylpropionic acid and preparation method thereof
  • 3-amino-3-arylpropionic acid and preparation method thereof
  • 3-amino-3-arylpropionic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The synthesis of embodiment 1 3-amino-3-phenylpropionic acid

[0022]

[0023] 3.18g of benzaldehyde (30mmol), 3.14g of malonic acid (30mmol) and 4.63g of ammonium acetate (60mmol) were refluxed in 60mL of methanol for 6 hours; after cooling to room temperature, filtered to obtain 3.67g of 3-amino-3-phenyl Propionic acid, yield 74%.

[0024] H NMR spectrum ( 1 H NMR, 300MHz, DMSO) δ: 12.20(s, 1H), 7.29-7.45(m, 5H), 5.15(s, 2H), 4.90(m, 1H), 2.87(dd, J=6.6, 1.8Hz, 1H), 2.62 (dd, J=6.6, 1.8 Hz, 1H). Mass spectrum (ESI): 166 (M+H + , 100), 188 (M+Na + , 42.5), 204 (M+K + , 15.3).

Embodiment 2

[0025] Example 2 Synthesis of 3-amino-3-(4-fluorophenyl)propionic acid

[0026]

[0027] Reflux 62g 4-fluorobenzaldehyde (0.5mol), 52g malonic acid (0.5mol) and 77g ammonium acetate (1mol) in 500mL ethanol for 8 hours; after cooling to room temperature, filter to obtain 73.3g 3-amino-3 - Phenylpropionic acid, yield 80%.

[0028] H NMR spectrum ( 1 H NMR, 300MHz, DMSO) δ: 12.18(s, 1H), 7.27(d, J=7.5Hz, 2H), 7.19(d, J=7.5Hz, 2H), 5.18(s, 2H), 4.92(m , 1H), 2.88 (dd, J=6.6, 1.8Hz, 1H), 2.65 (dd, J=6.6, 1.8Hz, 1H). Mass Spectrum (ESI): 184 (M+H + , 100), 206 (M+Na + , 32.8), 223 (M+K + , 12.6).

Embodiment 3

[0029] Example 3 Synthesis of 3-amino-3-(3-nitro-4-fluorophenyl)propionic acid

[0030]

[0031] Reflux 14.5g 3-nitro-4-fluorobenzaldehyde (0.087mol), 9.0g malonic acid (0.087mol) and 13.4g ammonium acetate (0.174mol) in ethanol for 6 hours; after cooling to room temperature, filter, 17.5 g of 3-amino-3-(3-nitro-4-fluorophenyl)propionic acid (0.076 mol) were obtained, yield 88%.

[0032] H NMR spectrum ( 1 H NMR, 300MHz, DMSO) δ: 12.22(s, 1H), 8.18(s, 1H), 7.67(d, J=7.5Hz, 1H), 7.48(d, J=7.5Hz, 1H), 4.94(m , 1H), 2.88 (dd, J=6.6, 1.8Hz, 1H), 2.64 (dd, J=6.6, 1.8Hz, 1H). Mass spectrum (ESI): 329 (M+H + , 100), 351 (M+Na + , 23.5), 367 (M+K + , 7.2).

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Abstract

The invention provides 3-amino-3-arylpropionic acid with the structure shown in the formula I in the specification, wherein R1 is substituted or non-substituted phenyl, substituted or non-substituted bicyclo or tricycloaryl or substituted or non-substituted monocyclo, bicyclo or tricycloaryl containing at least an N, O or S atom. The invention also provides a preparation method of 3-amino-3-arylpropionic acid. The unnatural amino acid 3-amino-3-arylpropionic acid can synthesize a series of polypeptide compounds with other amino acids. The polypeptide compounds have certain inhibitory activity against histone deacetylase (HDAC), are possibly used for preventing or treating diabetes, diabetes complications, acute promyelocytic leukemia (APL), inflammatory diseases, organ transplantation rejection, protozoan infection, autoimmune diseases or tumors, etc and have certain medicinal value. The preparation method has the beneficial effects of easily-obtained raw materials, simpleness, convenient operation and higher yield.

Description

technical field [0001] The present invention relates to a β-unnatural amino acid, in particular to 3-amino-3-aryl propionic acid and its preparation method. Background technique [0002] Unnatural amino acids are amino acids encoded by non-protein genes, and have important applications in frontier biotechnology research such as genomics and proteomics. For example, α-unnatural amino acids are widely used in the study of proteins, nucleosides and nucleic acids: they can limit the conformational flexibility of polypeptides, provide deoxyribonucleic acid or ribonucleic acid molecules with stable secondary structure, enhance the ability of polypeptides to enzymes stability and improve pharmacokinetics and biological activity; β-unnatural amino acids are precursors of β-lactams and key components of many potential enzyme inhibitors, and have quite interesting pharmacological activities. β-unnatural amino acids have become more and more important synthetic modules in the construc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/34C07C227/10C07D307/56C07D209/20C07K5/083A61K38/06A61P3/10A61P35/02A61P29/00A61P37/06A61P33/02A61P37/00A61P35/00
Inventor 许峰高源
Owner 合肥华纳生物医药科技有限公司