20696-57-5

Basic information

• Product Name: (S)-alpha-amino-1H-indole-3-propionamide
• Synonyms: (S)-alpha-amino-1H-indole-3-propionamide;(2S)-2-Amino-3-(1H-indole-3-yl)propionamide;(S)-α-Amino-1H-indole-3-propanamide;C00977;(S)-2-AMino-3-(1H-indol-3-yl)propanaMide
• CAS NO: 20696-57-5
• Molecular Formula: C₁₁H₁₃N₃O
• Molecular Weight: 203.24042
• EINECS: 243-977-0
• Mol File: 20696-57-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 254-255 °C (decomp)(Solv: methanol (67-56-1); ethyl acetate (141-78-6))
• Boiling Point: 498.7±40.0 °C(Predicted)
• Appearance: /
• Density: 1.302±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 15.99±0.50(Predicted)
• CAS DataBase Reference: (S)-alpha-amino-1H-indole-3-propionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-alpha-amino-1H-indole-3-propionamide(20696-57-5)
• EPA Substance Registry System: (S)-alpha-amino-1H-indole-3-propionamide(20696-57-5)

Safety Data

• Hazardous Substances Data: 20696-57-5(Hazardous Substances Data)

Usage

Definition

ChEBI: An amino acid amide that is the carboxamide of L-tryptophan.

Upstream product

• 20696-64-4 N-Carbobenzoxy-L-tryptophanamide 
• 4299-70-1 L-tryptophan methyl ester 
• 73-22-3 L-Tryptophan 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 5022-65-1 L-tryptophanamide hydrochloride 
• 50305-28-7 Cbz-L-Tryptophan-OSu 
• 54-12-6 Trp 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 

Downstream Products

• 89209-39-2 4-((1S,3S)-3-Carbamoyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-2,2-bis-phenylsulfanyl-butyric acid methyl ester 
• 6720-02-1 DL-tryptophanamide 
• 53707-84-9 (S)-1,2-diamino-3-indol-3-ylpropane 
• 2382-79-8 N^α-acetyl-L-tryptophan-amide 
• 89209-43-8 2,2-Bis-phenylsulfanyl-4-(S)-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl-butyric acid methyl ester 
• 89209-41-6 4-[(1S,3S)-3-Cyano-2-(2,2,2-trifluoro-acetyl)-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl]-2,2-bis-phenylsulfanyl-butyric acid methyl ester 
• 51952-40-0 L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L-arginyl-L-prolyl-glycine amide hydrochloride 
• 51871-39-7 L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosine methyl ester 
• 142822-22-8 L-pyroglutamyl-L-histidyl-L-trypthophyl-L-seryl-L-tyrosine tert-butyl ester 
• 52434-75-0 pGlu-His-Trp-Ser-Tyr 
• 910621-25-9 (12bS)-Ethyl 4-oxo-3-(phenylthio)-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-3-carboxylate 
• 439-66-7 (Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate 
• 1190078-25-1 (S)-2-(4-(dimethylamino)-4-phenylcyclohexylamino)-3-(1H-indol-3-yl)propanamide 
• 1219039-97-0 Nα-[3-(2-fluorophenyl)acryloyl]-L-tryptophanamide 

Relevant articles and documents

Cyclic hexapeptide dimers, antatollamides A and B, from the ascidian Didemnum molle. A tryptophan-derived auxiliary for L- and D-amino acid assignments

Two dimerized cyclic hexapeptides, antatollamides A 1 and B (2), were isolated from the colonial ascidian Didemnum molle collected in Pohnpei. The amino acid compositions and sequences were determined by interpretation of MS and 1D and 2D NMR data. Raney Ni reduction of antatollamide A cleaved the dimer to the corresponding monomeric cyclic hexapeptide with replacement of Cys by Ala. The amino acid configuration of 1 was established, after total hydrolysis, by derivatization with a new chiral reagent, (5-fluoro- 2,4-dinitrophenyl)-Nα-L-tryptophanamide (FDTA), prepared from L-Trp, followed by LCMS analysis; all amino acids were found to be L-configured except for D-Ala.

Synthetic method for chiral alpha-aminoamide compounds

The invention provides a synthetic method for chiral alpha-aminoamide compounds, belongs to the technical field of organic synthetic methodology, and concretely relates to a synthetic method for chiral alpha-aminoamide compounds, wherein the method has a simple process, low costs and good economy. The method comprises the following steps: 1, performing ammonolysis: adding substituted chiral alpha-aminocarboxylate hydrochloride into concentrated ammonia water, performing stirring for 4-12h under a room temperature, wherein each 1mmol substituted chiral alpha-aminocarboxylate hydrochloride is corresponding to 2-8mL the concentrated ammonia water; 2, after a reaction is finished, performing distillation for removing ammonia water after the reaction to obtain crude products chiral alpha-aminoamide compounds; and 3, performing filtration on the obtained crude products chiral alpha-aminoamide compounds by adopting a manner of adding a solvent or performing purification on the obtained crude products chiral alpha-aminoamide compounds through a manner of column chromatography which uses ammonia water as a mobile phase to obtain the products chiral alpha-aminoamide compounds. Compared with the prior art, a large number of an ammonia gas for ammonolysis is not needed in the method, the process and post-treatment are simple, costs are low and reaction time is short.

SUBSTITUTED CYCLOHEXYLDIAMINES

The invention relates to compounds that have an affinity to the μ-opioid receptor and the ORL 1-receptor, methods for their production, medications containing these compounds and the use of these compounds for the treatment of pain or other conditions.