18389-46-3

Basic information

• Product Name: DL-3-(2-thienyl)-beta-alanine
• Synonyms: DL-3-(2-thienyl)-beta-alanine;Einecs 242-268-3;b-Amino-2-thiophenepropanoic acid
• CAS NO: 18389-46-3
• Molecular Formula: C₇H₉NO₂S
• Molecular Weight: 171.21686
• EINECS: 242-268-3
• Mol File: 18389-46-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 327.6°Cat760mmHg
• Flash Point: 151.9°C
• Appearance: /
• Density: 1.345g/cm³
• Vapor Pressure: 8.12E-05mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: DL-3-(2-thienyl)-beta-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: DL-3-(2-thienyl)-beta-alanine(18389-46-3)
• EPA Substance Registry System: DL-3-(2-thienyl)-beta-alanine(18389-46-3)

Safety Data

• Hazardous Substances Data: 18389-46-3(Hazardous Substances Data)

Usage

General Description

DL-3-(2-thienyl)-beta-alanine, also known as 3-(2-thienyl)-beta-alanine, is a chemical compound with the formula C7H9NO2S. It is a beta-alanine derivative with a thienyl group attached to the third carbon atom of the beta-alanine molecule. DL-3-(2-thienyl)-beta-alanine is commonly used in pharmaceutical and research applications due to its potential therapeutic properties. It has been studied for its potential use in the treatment of neurological disorders, such as epilepsy and schizophrenia, as well as for its role in enhancing exercise performance. DL-3-(2-thienyl)-beta-alanine is known to interact with the GABAergic system in the brain and may have anti-convulsant and anti-anxiety effects. Overall, this compound has shown promise in various research studies and continues to be investigated for its potential medical uses.

InChI:InChI=1/C7H9NO2S/c8-5(4-7(9)10)6-2-1-3-11-6/h1-3,5H,4,8H2,(H,9,10)

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 141-82-2 malonic acid 
• 631-61-8 ammonium acetate 

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.

Burkholderia cepacia lipase is an excellent enzyme for the enantioselective hydrolysis of β-heteroaryl-β-amino esters

The enantioselective (E >200) lipase PS-catalysed hydrolysis of β-heteroaryl-β-amino esters is described. The reactions were performed with H2O (0.5 equiv) in either diisopropyl ether or tert-butyl methyl ether at 25 °C. The resulting β-heteroaryl-substituted β-amino acid enantiomers were formed in high enantiomeric excess (ee ≥ 97%) and in good yield (≥40%).