5678-47-7

Basic information

• Product Name: 3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID
• Synonyms: RARECHEM AK HC P253;DL-3-AMINO-3-(3'-NITROPHENYL)PROPIONIC ACID;DL-3-AMINO-3-(3-NITRO-PHENYL)-PROPIONIC ACID;3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID;3-AMINO-3-(3-NITROPHENYL)PROPIONIC ACID;3-(3-NITROPHENYL)-DL-BETA-ALANINE;3-azanyl-3-(3-nitrophenyl)propanoic acid;(RS)-3-Amino-3-(3-nitrophenyl)-propionic acid
• CAS NO: 5678-47-7
• Molecular Formula: C₉H₁₀N₂O₄
• Molecular Weight: 210.19
• Product Categories: B-Amino
• Mol File: 5678-47-7.mol

Chemical Properties

• Melting Point: 213-215°C
• Boiling Point: 384.5°C at 760mmHg
• Flash Point: 186.4°C
• Appearance: /
• Density: 1.404g/cm³
• Vapor Pressure: 1.34E-06mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: 2-8°C
• PKA: 3.52±0.10(Predicted)
• CAS DataBase Reference: 3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID(5678-47-7)
• EPA Substance Registry System: 3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID(5678-47-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5678-47-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID is utilized as a key intermediate in the synthesis of various pharmaceuticals, given its unique structural features that facilitate the creation of new drug molecules. Its presence in the synthesis process aids in the development of treatments for different medical conditions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID is employed as a reagent, contributing to the advancement of research and the discovery of novel therapeutic agents. Its chemical properties make it a valuable asset in the design and synthesis of complex organic molecules with potential medicinal applications.
Used in Organic Synthesis:
3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID also serves as a building block in organic synthesis, enabling the construction of more intricate molecular structures. Its role in this process is crucial for the development of advanced organic compounds with specific properties and potential uses in various industries, including pharmaceuticals, materials science, and chemical research.
Used in Research and Development:
3-AMINO-3-(3-NITROPHENYL)PROPANOIC ACID is used in research and development settings to explore its potential in creating new chemical entities and understanding its interactions with biological systems. This helps in identifying its possible therapeutic effects and applications in medicine.

InChI:InChI=1/C9H10N2O4/c10-8(5-9(12)13)6-2-1-3-7(4-6)11(14)15/h1-4,8H,5,10H2,(H,12,13)

Upstream product

• 555-68-0 m-Nitrocinnamic Acid 
• 141-82-2 malonic acid 
• 99-61-6 3-nitro-benzaldehyde 
• 7647-01-0 hydrogenchloride 
• 859286-58-1 (α-amino-3-nitro-benzyl)-malonic acid diethyl ester 
• 861595-61-1 3-hydroxyamino-3-(3-nitro-phenyl)-propionohydroxamic acid 
• 7732-18-5 water 
• 5396-71-4 ethyl 3-(3-nitrophenyl)acrylate 

Downstream Products

• 18071-62-0 3-amino-3-(3-amino-phenyl)-propionic acid 
• 790196-47-3 3-(2-amino-acetylamino)-3-(3-nitro-phenyl)-propionic acid methyl ester 
• 406692-16-8 3-(2-tert-butoxycarbonylamino-acetylamino)-3-(3-nitro-phenyl)-propionic acid methyl ester 
• 736175-01-2 3-(3-nitro-phenyl)-3-{2-[4-(pyridin-2-ylamino)-butyrylamino]-acetylamino}-propionic acid methyl ester 
• 284492-22-4 C₁₄H₁₈N₂O₆ 
• 259195-70-5 methyl 3-benzyloxycarbonylamino-3-(3-nitrophenyl)propionate 
• 787544-61-0 (R)-3-amino-3-(3-nitrophenyl)propanoic acid 
• 555-68-0 (E)-3-Nitrocinnamic acid 
• 19883-74-0 (2S)-2-amino-3-(3-nitrophenyl)propanoic acid 
• 91952-08-8 C₁₁H₁₂N₂O₅ 
• 1426822-64-1 C₁₃H₁₃F₃N₂O₅ 
• 640238-28-4 3-benzamido-3-(3-nitrophenyl)propanoic acid 
• 1269634-20-9 C₁₇H₁₆N₂O₅ 
• 1257211-85-0 (R)-1-[3-benzamido-3-(3-nitrophenyl)propanamido]-3-methylbutylboronic acid 

Relevant articles and documents

Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts

An enzymatic strategy for the preparation of (R)-β-arylalanines employing phenylalanine aminomutase and ammonia lyase (PAM and PAL) enzymes has been demonstrated. Candidate PAMs with the desired (S)-selectivity from Streptomyces maritimus (EncP) and Bacillus sp. (PabH) were identified via sequence analysis using a well-studied template sequence. The newly discovered PabH could be linked to the first ever proposed biosynthesis of pyloricidin-like secondary metabolites and was shown to display better β-lyase activity in many cases. In spite of this, a method combining the higher conversion of EncP with a strict α-lyase from Anabaena variabilis (AvPAL) was found to be more amenable, allowing kinetic resolution of five racemic substrates and a preparative-scale reaction with >98% (R) enantiomeric excess. This work represents an improved and enantiocomplementary method to existing biocatalytic strategies, allowing simple product separation and modular telescopic combination with a preceding chemical step using an achiral aldehyde as starting material. (Figure presented.).

Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)

All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities. All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 μM (compared to liarozole (IC50 = 2.45 μM) and S8 (IC50 = 3.21 μM)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of β-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development.

Carica papaya lipase catalysed resolution of β-amino esters for the highly enantioselective synthesis of (S)-dapoxetine

An efficient synthesis of the (S)-3-amino-3-phenylpropanoic acid enantiomer has been achieved by Carica papaya lipase (CPL) catalysed enantioselective alcoholysis of the corresponding racemic N-protected 2,2,2-trifluoroethyl esters in an organic solvent. A high enantioselectivity (E > 200) was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. Based on the resolution of a series of amino acids, it was found that the structure of the substrate has a profound effect on the CPL-catalysed resolution. The enantioselectivity and reaction rate were significantly enhanced by switching the conventional methyl ester to an activated trifluoroethyl ester. When considering steric effects, the substituted phenyl and amino groups should not both be large for the CPL-catalysed resolution. The mechanism of the CPL-catalysed enantioselective alcoholoysis of the amino acids is discussed to delineate the substrate requirements for CPL-catalysed resolution. Finally, the reaction was scaled up, and the products were separated and obtained in good yields (≥ 80 %). The (S)-3-amino-3- phenylpropanoic acid obtained was used as a key chiral intermediate in the synthesis of (S)-dapoxetine with very high enantiomeric excess (> 99 %). A carica papaya lipase catalysed resolution of N-protected β-phenylalanine esters has been developed. High enantioselectivity was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. After 50 % conversion, the products were separated and used as key chiral intermediates for the synthesis of (S)-dapoxetine with > 99 % ee. Copyright

Integrin-Mediated drug targeting

The present invention relates to cytostatics which have a tumour-specific action as a result of linkage to αvβ3 integrin antagonists via preferred linking units. The preferred linking units guarantee serum stability of the conjugate of cytostatic and αvβ3 integrin antagonist and at the same time the desired intracellular action in tumour cells as a result of their enzymatic or hydrolytic cleavability with release of the cytostatic.

Kinetic resolution of oxazinones: An organocatalytic approach to enantiomerically pure β-amino acids

(Chemical Equation Presented) A profitable split: An organocatalytic resolution converts readily available racemic oxazinones 1 into valuable enantiomerically pure β-amino acid derivatives 2 (> 99% ee of the remaining 1 at 53% conversion; 88% ee of the ester 2). This catalytic ring-opening reaction requires as little as 1 mol% of the modular and readily accessible thiourea organocatalyst 3.

Conformationally restricted analogs of deoxynegamycin

Deoxynegamycin (1b) is a protein synthesis inhibitor with activity against Gram-negative (GN) bacteria. A series of conformationally restricted analogs were synthesized to probe its bioactive conformation. Indeed, some of the constrained analogs were found to be equal or better than deoxynegamycin in protein synthesis assay (1b, IC50=8.2μM; 44, IC 50=6.6μM; 35e2, IC50=1μM). However, deoxynegamycin had the best in vitro whole cell antibacterial activity (Escherichia coli, MIC=4-16μg/mL; Klebsiella pneumoniae, MIC=8μg/mL) suggesting that other factors such as permeation may also be contributing to the overall whole cell activity. A new finding is that deoxynegamycin is efficacious in an E. coli murine septicemia model (ED50=4.8mg/kg), providing further evidence of the favorable in vivo properties of this class of molecules.

β-alanine derivatives

The invention relates to β-alanine derivatives of formula (I), wherein Q1, Q2, Q3, Q4, R1, R2, R3, R4, R5, R6and n have the meaning as disclosed

Nanomolar small molecule inhibitors for ανβ6, ανβ5, and ανβ3 integrins

Integrin adhesion receptors frequently recognize a core amino acid sequence, Arg-Gly-Asp, in their target ligands. Inhibitors with the ability to inhibit one or a small subset of such RGD-dependent integrins have been invaluable in defining their biological function. Here, we have characterized low molecular weight inhibitors for their ability to specifically inhibit ανβ6 integrin, a fibronectin/tenascin receptor. As of yet, no nonpeptidic inhibitor of ανβ6 was known. New peptidomimetic and nonpeptidic compounds were examined in isolated integrin binding assays and in cell adhesion assays for their ability to block ανβ6, ανβ3, ανβ5, and αIIbβ3 integrins. The compounds are based on an aromatically substituted β amino acid or glutaric acid derivative as an acidic center and an aminopyridyl or guanidyl residue as a basic mimetic. We found several classes of inhibitors with different selectivities, especially mono- or biselectivity on the αν-integrins ανβ6 and ανβ3, and nanomolar activity. Furthermore, nearly all compounds are inactive on αIIbβ3. Compound 11 is the first specific, peptidomimetic inhibitor of the ανβ6 integrin receptor.