3270-89-1

Basic information

• Product Name: 3-AMINO-3-(2-THIENYL)PROPANOIC ACID
• Synonyms: AKOS B013351;3-AMINO-3-THIEN-2-YLPROPANOIC ACID;3-AMINO-3-(THIOPHEN-2-YL)PROPANOIC ACID;3-AMINO-3-THIOPHEN-2-YL-PROPIONIC ACID;3-AMINO-3-(2-THIENYL)PROPANOIC ACID;3-AMINO-3-(2-THIENYL)-PROPIONIC ACID;3-(2-THIENYL)-BETA-ALANINE;3-Amino-3-(2-thienyl)propanoic acid ,97%
• CAS NO: 3270-89-1
• Molecular Formula: C7H9NO2S
• Molecular Weight: 171.22
• Product Categories: B-Amino
• Mol File: 3270-89-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 205-207°C
• Boiling Point: 327.6 °C at 760mm Hg
• Flash Point: 151.9 °C
• Appearance: /
• Density: 1.345 g/cm³
• CAS DataBase Reference: 3-AMINO-3-(2-THIENYL)PROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-3-(2-THIENYL)PROPANOIC ACID(3270-89-1)
• EPA Substance Registry System: 3-AMINO-3-(2-THIENYL)PROPANOIC ACID(3270-89-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 3270-89-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-white solid

Upstream product

• 2021-58-1 rac-3-(2-thienyl)alanine 
• 93447-77-9 ethyl (+/-)-3-amino-3-(2-thienyl)propanoate 
• 67206-29-5 N-Chloracetyl-β-2-thienyl-DL-β-alanin 
• 18389-46-3 3-amino-3-(thiophen-2-yl)propanoic acid 
• 22951-96-8 L-3-(2-thienyl)alanine 
• 98-03-3 thiophene-2-carbaldehyde 
• 631-61-8 ammonium acetate 
• 141-82-2 malonic acid 

Downstream Products

• 93447-77-9 ethyl (+/-)-3-amino-3-(2-thienyl)propanoate 
• 194229-21-5 3-(5-bromo-2-thienyl)-3-[(2,2,2-trifluoroacetyl)amino]propanoic acid 

Relevant articles and documents

Aminothiaindanone as an Accessible Scaffold for a Three-Point Chemical Diversity

Aminothiaindanone heterocycle appears to be a scaffold of interest in medicinal chemistry. To increase the chemical diversity in this series, the introduction of three-point chemical diversity on the cyclopenta[ b ]thiophen-4-one scaffold was explored. About thirty newly functionalized thiophene-containing bicycles were obtained using various chemical reactions, paving the way for novel possibilities in medicinal chemistry projects.

Synthesis, molecular docking and biological evaluation of novel phthaloyl derivatives of 3-amino-3-aryl propionic acids as inhibitors of Trypanosoma cruzi trans-sialidase

In the last two decades, trans-sialidase of Trypanosoma cruzi (TcTS) has been an important pharmacological target for developing new anti-Chagas agents. In a continuous effort to discover new potential TcTS inhibitors, 3-amino-3-arylpropionic acid derivatives (series A) and novel phthaloyl derivatives (series B, C and D) were synthesized and molecular docking, TcTS enzyme inhibition and determination of trypanocidal activity were carried out. From four series obtained, compound D-11 had the highest binding affinity value (?11.1 kcal/mol) compared to reference DANA (?7.8 kcal/mol), a natural ligand for TS enzyme. Furthermore, the 3D and 2D interactions analysis of compound D-11 showed a hydrogen bond, π-π stacking, π-anion, hydrophobic and Van der Waals forces with all important amino acid residues (Arg35, Arg245, Arg314, Tyr119, Trp312, Tyr342, Glu230 and Asp59) on the active site of TcTS. Additionally, D-11 showed the highest TcTS enzyme inhibition (86.9% ± 5) by high-performance ion exchange chromatography (HPAEC). Finally, D-11 showed better trypanocidal activity than the reference drugs nifurtimox and benznidazole with an equal % lysis (63 ± 4 and 65 ± 2 at 10 μg/mL) and LC50 value (52.70 ± 2.70 μM and 46.19 ± 2.36 μM) on NINOA and INC-5 strains, respectively. Therefore, D-11 is a small-molecule with potent TcTS inhibition and a strong trypanocidal effect that could help in the development of new anti-Chagas agents.

Influence of the aromatic moiety in α- And β-arylalanines on their biotransformation with phenylalanine 2,3-aminomutase from: Pantoea agglomerans

In this study enantiomer selective isomerization of various racemic α- and β-arylalanines catalysed by phenylalanine 2,3-aminomutase from Pantoea agglomerans (PaPAM) was investigated. Both α- and β-arylalanines were accepted as substrates when the aryl moiety was relatively small, like phenyl, 2-, 3-, 4-fluorophenyl or thiophen-2-yl. While 2-substituted α-phenylalanines bearing bulky electron withdrawing substituents did not react, the corresponding substituted β-aryl analogues were converted rapidly. Conversion of 3- and 4-substituted α-arylalanines happened smoothly, while conversion of the corresponding β-arylalanines was poor or non-existent. In the range of pH 7-9 there was no significant influence on the conversion of racemic α- or β-(thiophen-2-yl)alanines, whereas increasing the concentration of ammonia (ammonium carbonate from 50 to 1000 mM) inhibited the isomerization progressively and decreased the amount of the by-product (i.e. (E)-3-(thiophen-2-yl)acrylic acid was detected). In all cases, the high ee values of the products indicated excellent enantiomer selectivity and stereospecificity of the isomerization except for (S)-2-nitro-α-phenylalanine (ee 92%) from the β-isomer. Substituent effects were rationalized by computational modelling revealing that one of the main factors controlling biocatalytic activity was the energy difference between the covalent regioisomeric enzyme-substrate complexes.