3-{[2-(1H-indol-3-yl)ethyl]carbamoyl}propanoic acid

Base Information

• Chemical Name: 3-{[2-(1H-indol-3-yl)ethyl]carbamoyl}propanoic acid
• CAS No.: 92256-33-2
• Molecular Formula: C₁₄H₁₆N₂O₃
• Molecular Weight: 260.293
• DSSTox Substance ID: DTXSID80383969
• Nikkaji Number: J1.533.698F
• Wikidata: Q82175813
• Mol file: 92256-33-2.mol

Synonyms:92256-33-2;3-{[2-(1H-indol-3-yl)ethyl]carbamoyl}propanoic acid;4-((2-(1H-Indol-3-yl)ethyl)amino)-4-oxobutanoic acid;N-[2-(3-indolyl)ethyl]succinamic acid;3-{[2-(1H-indol-3-yl)ethyl]carbamoyl}propanoicacid;4-{[2-(1H-indol-3-yl)ethyl]amino}-4-oxobutanoic acid;4-[2-(1H-indol-3-yl)ethylamino]-4-oxobutanoic acid;IESA;SCHEMBL918964;DTXSID80383969;FMXUSNAWMLGDCZ-UHFFFAOYSA-N;MFCD00205991;AKOS005105879;JS-1307;N-[2-(3-indolyl)ethyl] succinamic acid;4-((2-(1H-Indol-3-yl)ethyl)amino)-4-oxobutanoicacid

Chemical Property of 3-{[2-(1H-indol-3-yl)ethyl]carbamoyl}propanoic acid

Chemical Property:

• PSA: 85.68000
• LogP: 2.53170
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 260.11609238
• Heavy Atom Count: 19
• Complexity: 333

Purity/Quality:

4-[[2-(1H-Indol-3-yl)ethyl]amino]-4-oxobutanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCNC(=O)CCC(=O)O
• Uses: 4-[[2-(1H-Indol-3-yl)ethyl]amino]-4-oxobutanoic Acid is an intermediate in the synthesis of Canthin-6-one (C175635), which is used as an anticancer agent compromising cancer cells showing multi-drug resistance. Also used in the synthesis of β-carbolinium compounds as antimalarial agents.

Technology Process of 3-{[2-(1H-indol-3-yl)ethyl]carbamoyl}propanoic acid

There total 3 articles about 3-{[2-(1H-indol-3-yl)ethyl]carbamoyl}propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

succinic acid anhydride (108-30-5) + tryptamine (61-54-1) → N-(2-indol-3-yl-ethyl)-succinamic acid (92256-33-2)

Guidance literature:

In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/np050250z

Reference yield:

tryptamine (61-54-1) + succinyl-coenzyme A (604-98-8) → N-(2-indol-3-yl-ethyl)-succinamic acid (92256-33-2)

Guidance literature:

With dipyridin-4-yl disulfide; wild-type arylalkylamine N-acyltransferase from Tribolium castaneum; In aq. buffer; pH=8; Kinetics; Enzymatic reaction;

DOI:10.1021/acschembio.9b00973

Reference yield:

→ N-(2-indol-3-yl-ethyl)-succinamic acid (92256-33-2)

Guidance literature:

Bernsteinsaeureanhydrid, Tryptamin (evak. Rohr, 130-140grad) (neben entspr. Imid);

upstream raw materials:

succinic acid anhydride

tryptamine

succinyl-coenzyme A

Downstream raw materials:

canthin-6-one-3-N-oxide

3-(9H-Pyrido<3,4-b>indol-1-yl)propansaeure-methylester

canthin-6-one

N'-<3-(methoxycarbonyl)propanoyl>tryptamine