167887-15-2

Basic information

• Product Name: 3-(1,3-dioxoisoindolin-2-yl)-3-(naphthalen-2-yl)propanoic acid
• Synonyms: 3-(1,3-dioxoisoindolin-2-yl)-3-(naphthalen-2-yl)propanoic acid
• CAS NO: 167887-15-2
• Molecular Weight: 345.354
• Mol File: 167887-15-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-(1,3-dioxoisoindolin-2-yl)-3-(naphthalen-2-yl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,3-dioxoisoindolin-2-yl)-3-(naphthalen-2-yl)propanoic acid(167887-15-2)
• EPA Substance Registry System: 3-(1,3-dioxoisoindolin-2-yl)-3-(naphthalen-2-yl)propanoic acid(167887-15-2)

Safety Data

• Hazardous Substances Data: 167887-15-2(Hazardous Substances Data)

Upstream product

• 85-44-9 phthalic anhydride 
• 129042-57-5 3-amino-3-(2-naphthyl)propionic acid 

Relevant articles and documents

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.