57105-53-0

Usage

Uses

Used in Pharmaceutical Industry:
Tryptophan, N-indol-3-ylacetyl(6CI) is used as a key intermediate in the synthesis of various pharmaceutical compounds, such as β-D-galactosidase and β-D-glucosidase inhibitors. These inhibitors have potential applications in the treatment of various diseases and conditions, including lysosomal storage disorders and certain types of cancer.
Used in Agricultural Industry:
In the agricultural industry, Tryptophan, N-indol-3-ylacetyl(6CI) is utilized in the development of bioactive compounds that can help regulate plant growth and development. Its involvement in the control of auxin activity makes it a valuable tool for understanding and manipulating plant responses to various environmental stimuli, which can lead to improved crop yields and resistance to diseases.
Used in Research and Development:
Tryptophan, N-indol-3-ylacetyl(6CI) is also used as a research tool in the field of molecular biology and biochemistry. It can be employed in the study of protein-protein interactions, enzyme inhibition, and other cellular processes, contributing to the advancement of scientific knowledge and the development of new therapeutic strategies.

InChI:InChI=1/C21H19N3O3/c25-20(10-14-12-23-18-8-4-2-6-16(14)18)24-19(21(26)27)9-13-11-22-17-7-3-1-5-15(13)17/h1-8,11-12,19,22-23H,9-10H2,(H,24,25)(H,26,27)/t19-/m0/s1

Upstream product

• 50720-05-3 indolyl acetyl chloride 
• 73-22-3 L-Tryptophan 
• 1080025-88-2 1-(1H-benzotriazol-1-yl)-2-(1H-indol-3-yl)ethanone 
• 87-51-4 indole-3-acetic acid 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 

Relevant academic research and scientific papers

Preparation of synthetic auxin-amino acid conjugates

Auxin amide conjugates are regulators of the most important auxin, indole-3-acetic acid (IAA), which is considered responsible for many important processes within the plants. Herein, amide conjugates of IAA were synthesized employing a simple and efficient coupling method with WSCI·HCl, a water-soluble condensing reagent, in the presence of 1-hydroxybenzotriazole. IAA conjugates with 10 amino acids along with their corresponding methyl esters were prepared in excellent yields, up to 95%, aiming to facilitate their identification in plant species. Eight IAA-amino acid methyl ester conjugates are characterized here for the first time.

Tryptophan and thiosemicarbazide derivatives: Design, synthesis, and biological evaluation as potential β-D-galactosidase and β-D-glucosidase inhibitors

Glycosidases, including β-D-galactosidase and β-D-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several β-D-galactosidase and β-D-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as β-D-galactosidase and β-D-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 μM) and 4d (49 % inhibition at 100 μM) exhibited the best inhibitory bioactivities against β-D-galactosidase and β-D-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.

Syntheses of IAA- and IPA-amino acid conjugates

(Chemical Equation Presented) Amino acid derivatives of IAA and IPA are prepared conveniently and efficiently by coupling of readily available 2a-b with diverse free amino acids 3a-g and (3c+3c′) to give compounds 4a-j, (4c+4c′) and (4h+4h′) in 38-70% yie

Therapeutic and diagnostic ligand systems comprising transport molecule binding properties and medicaments containing the same

The invention relates to transport molecule binding ligand compounds which comprise a therapeutically and/or diagnostically active substance and a carrier molecule-affine substance with a high association constant to the carrier molecule. The invention also relates to medicaments containing these ligand compounds and to diagnostic kits.