18389-46-3

Usage

Uses

Used in Pharmaceutical Applications:
DL-3-(2-thienyl)-beta-alanine is used as a therapeutic agent for its potential role in treating neurological disorders. It has been studied for its efficacy in managing conditions such as epilepsy and schizophrenia, attributed to its interaction with the GABAergic system in the brain, which may confer anti-convulsant and anti-anxiety effects.
Used in Research Applications:
In the research field, DL-3-(2-thienyl)-beta-alanine serves as a valuable compound for investigating its potential medical uses. Its effects on the central nervous system and its capacity to enhance exercise performance are areas of active study, with the aim of uncovering further applications in healthcare and sports medicine.
Used in Neurological Disorder Treatment:
DL-3-(2-thienyl)-beta-alanine is utilized as a treatment option for neurological disorders due to its potential to modulate neurotransmission and exhibit neuroprotective properties, offering a novel approach to managing epilepsy and schizophrenia.
Used in Exercise Performance Enhancement:
DL-3-(2-thienyl)-beta-alanine is also used in applications aimed at enhancing exercise performance, capitalizing on its effects on muscle metabolism and physical endurance, which could be beneficial for athletes and individuals engaged in strenuous physical activities.

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

• 104883-48-9 3-aminoheptanoic acid 
• 93447-77-9 ethyl (+/-)-3-amino-3-(2-thienyl)propanoate 
• 188812-40-0 methyl β-aminothiophene-2-propanoate 
• 101777-34-8 3-(toluene-4-sulfonylamino)-heptanoic acid 
• 1124-65-8 3-(2-thienyl)-2-propenoic acid 
• 73495-10-0 (R)-3-Amino-3-thiophen-2-yl-propionic acid 
• 22951-96-8 L-3-(2-thienyl)alanine 
• 194229-21-5 3-(5-bromo-2-thienyl)-3-[(2,2,2-trifluoroacetyl)amino]propanoic acid 

Relevant academic research and scientific papers

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.

Iridium-catalysed C-H borylation of β-aryl-aminopropionic acids

Iridium-catalysed catalytic, regioselective C-H borylation of β-aryl-aminopropionic acid derivatives gives access to 3,5-functionalised protected β-aryl-aminopropionic acid boronates. The synthetic versatility of these new boronates is demonstrated through sequential one-pot functionalisation reactions to give diverse building blocks for medicinal chemistry. The C-H borylation is also effective for dipeptide substrates. We have exemplified this methodology in the synthesis of a pan αv integrin antagonist.

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.

1-(3-AMINOPROPYL) SUBSTITUTED CYCLIC AMINE COMPOUNDS, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

Provided are 1-(3-aminopropyl) substituted cyclic amine compounds as represented by formula (I), pharmaceutically acceptable salts, enantiomers, diastereoisomers, racemates and mixtures thereof, and a method of synthesizing said 1-(3-aminopropyl) substituted cyclic amine compounds by using aromatic heterocyclic formaldehyde as raw material. Said compounds can be used as CCR 5 antagonist for the treatment of HIV infection.

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%).

PLATELET ADP RECEPTOR INHIBITORS

Compounds are provided which are useful as platelet ADP receptor inhibitors, for treating thrombosis and for reducing the likelihood and/or severity of a secondary ischemic event in a patient.

Structure-activity relationships of 1,3,5-triazine-2,4,6-triones as human gonadotropin-releasing hormone receptor antagonists

SAR studies of 1,3,5-triazine-2,4,6-triones as human gonadotropin-releasing hormone receptor antagonists resulted in potent compounds. The best compound from the series had a binding affinity of 2 nM.

Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium

The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered. 2005 Pleiades Publishing, Inc.

2-CYANOPYRROLES AND THEIR ANALOGUES AS DDP-IV INHIBITORS

The present invention relates to therapeutically active and selective inhibitors of the enzyme DPP-IV having the formula I: (I) The invention furthermore relates to pharmaceutical compositions comprising the compounds and the use of such compounds for the manufacture of medicaments for treating diseases that are associated with proteins which are subject to inactivation by DPP-IV, such as type 2 diabetes and obesity.

Candida antarctica lipase A - A powerful catalyst for the resolution of heteroaromatic β-amino esters

Enantioselective acylations of 3-amino-3-heteroarylpropanoates (ArCH(NH2)CH2CO2Et; Ar=2- or 3-thienyl or -furyl) were performed in the presence of Candida antarctica lipase A. As a result of the excellent chemo- and enantioselectivities (E >100), gram-scale resolutions were carried out in ethyl butanoate. The hydrochloride salts of the unreacted R substrates and the butanamides of the reactive S enantiomers were thus prepared.