26384-48-5

Basic information

• Product Name: 3-(1H-Indol-3-ylmethyl)-6-methyl-2,5-piperazinedione
• Synonyms: 3-(1H-Indol-3-ylmethyl)-6-methyl-2,5-piperazinedione
• CAS NO: 26384-48-5
• Molecular Formula: C14H15 N3 O2
• Molecular Weight: 257.29
• Mol File: 26384-48-5.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(1H-Indol-3-ylmethyl)-6-methyl-2,5-piperazinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1H-Indol-3-ylmethyl)-6-methyl-2,5-piperazinedione(26384-48-5)
• EPA Substance Registry System: 3-(1H-Indol-3-ylmethyl)-6-methyl-2,5-piperazinedione(26384-48-5)

Safety Data

• Hazardous Substances Data: 26384-48-5(Hazardous Substances Data)

Upstream product

• 21631-12-9 DL-alanine-DL-tryptophan 
• 204980-52-9 D-alanyl-L-tryptophan methyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 28944-99-2 Z-D-Ala-L-Trp-OMe 
• 76932-10-0 methyl (S)-alanyl-(S)-tryptophanate 
• 28944-98-1 Z-L-Ala-L-Trp-OMe 
• 207349-24-4 Boc-Ala-Trp-OMe 
• 300766-86-3 (3S,6S)-6-(3'-indolylmethyl)-3-methyl-1-(2,4-dimethoxybenzyl)-2,5-piperazinedione 
• 168766-64-1 methyl (S)-N'-(2,4-dimethoxybenzyl)tryptophanate 
• 300766-84-1 methyl N-tert-butoxycarbonyl-N'-(2'',4''-dimethoxybenzyl)-(S)-alanyl-(S)-tryptophanate 
• 4299-70-1 L-tryptophan methyl ester 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 73-22-3 L-Tryptophan 
• 63430-66-0 N^α-(tert-butoxycarbonyl)-L-tryptophyl-L-alanine methyl ester 

Downstream Products

• 1429318-81-9 C₂₂H₁₈BrF₃N₄O₃ 
• 1429318-54-6 C₂₀H₁₉N₃O₂ 
• 1859-87-6 Echinulin 
• 374114-86-0 (3S,6R)-1-(o-Azidobenzoyl)-3-methyl-6-(3-indolylmethyl)-2,5-piperazinedione 
• 374114-89-3 (3R,6S)-1-(o-Azidobenzoyl)-3-(3-indolylmethyl)-6-methyl-2,5-piperazinedione 
• 1429318-56-8 C₂₀H₁₉N₃O₂ 

Relevant articles and documents

Oxidative couplings on tryptophan-based diketopiperazines leading to fused and bridged chemotypes

New chemotypes are obtained from tryptophan-containing diketopiperazines through selective C-C or C-N intramolecular oxidative couplings. The choice of the oxidant source dictates the outcome of the reaction.

Copper-catalyzed diastereoselective arylation of tryptophan derivatives: Total synthesis of (+)-naseseazines A and B

A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site-and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.

Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides

Fourteen tryptophan-containing cyclic dipeptides 1a-14a, including all four stereoisomers of cyclo-Trp-Pro and cyclo-Trp-Ala, were converted to their C2-regularly prenylated derivatives 1b-14b in the presence of dimethylallyl diphosphate by using the purified recombinant FtmPT1 as catalyst. The enzyme products were isolated on HPLC in preparative scales and their structures were elucidated by NMR and MS analyses. The cytotoxic effects of the prenylated products and their substrates were tested with human leukemia K562 and ovarian cancer A2780 sens and A2780 CisR cell lines. Preliminary results have been clearly shown that prenylation at C2 led to a significant increase of the cytotoxicity of the tested cyclic dipeptides in all the 14 cases. The second amino acid and the stereochemistry of tryptophan moiety of the cyclic dipeptides showed less influence on the cytotoxicity of the tested compounds.