Deoxybrevianamide E

Base Information

• Chemical Name: Deoxybrevianamide E
• CAS No.: 34610-68-9
• Molecular Formula: C21H25N3O2
• Molecular Weight: 351.4421
• UNII: GJ20E60VAQ
• DSSTox Substance ID: DTXSID60956110
• Nikkaji Number: J92.748A
• Wikidata: Q27140204
• Metabolomics Workbench ID: 66163
• Mol file: 34610-68-9.mol

Synonyms:Deoxybrevianamide E;34610-68-9;Desoxybrevianamide E;UNII-GJ20E60VAQ;GJ20E60VAQ;(3S,8aS)-3-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;Pyrrolo(1,2-a)pyrazine-1,4-dione, 3-((2-(1,1-dimethyl-2-propen-1-yl)-1H-indol-3-yl)methyl)hexahydro-, (3S,8aS)-;cyclo-2-(1,1-dimethylallyl)-L-tryptophyl-L-proline;cyclo-L-prolyl-2-(1,1-dimethylallyl)-L-tryptophan;L-Prolyl-2-(1,1-dimethylallyl)-L-tryptophan anhydride;(3S,8aS)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;CHEBI:72948;DTXSID60956110;NSC789233;NSC-789233;HY-125538;CS-0092159;C20636;Q27140204;(3S,8aS)-3-[[2-(1,1-dimethylallyl)-1H-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;1-Hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazin-4(3H)-one

Chemical Property of Deoxybrevianamide E

Chemical Property:

• Vapor Pressure: 2.71E-15mmHg at 25°C
• Boiling Point: 619.9°Cat760mmHg
• Flash Point: 328.7°C
• PSA: 65.20000
• Density: 1.24g/cm³
• LogP: 2.93010
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 351.19467705
• Heavy Atom Count: 26
• Complexity: 602

Purity/Quality:

97% ^*data from raw suppliers

Deoxybrevianamide E ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C=C)C1=C(C2=CC=CC=C2N1)CC3C(=O)N4CCCC4C(=O)N3
• Isomeric SMILES: CC(C)(C=C)C1=C(C2=CC=CC=C2N1)C[C@H]3C(=O)N4CCC[C@H]4C(=O)N3
• Description: Deoxybrevianamide E is an alkaloid fungal metabolite that has been found in Aspergillus. It is a precursor in the biosynthesis of notoamides.
• Uses: Deoxybrevianamide E is an alkaloidal diketopiperazine. Deoxybrevianamide E is an alkaloidal diketopiperazine derived from tryptophan and proline, isolated from Aspergillus and Penicillium species. There are no reports of intensive investigation of deoxybrevianamide E.

Technology Process of Deoxybrevianamide E

There total 21 articles about Deoxybrevianamide E 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: 58.8%

methyl 3-<2-(1,1-dimethylallyl)indol-3-ylmethyl>-1,4-dioxoperhydropyrrolo<1,2-a>pyrazine-3-carboxylate (75526-76-0,75557-84-5) → deoxybrevianamide E (34610-68-9)

Guidance literature:

With magnesium chloride; In dimethyl sulfoxide; at 130 - 140 ℃; for 2.5h;

DOI:10.1039/P19810000959

Reference yield: 55.0%

(S)-3-[2-(1,1-Dimethyl-allyl)-1H-indol-3-ylmethyl]-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazine-3-carboxylic acid (75526-77-1,75557-85-6) → deoxybrevianamide E (34610-68-9) + L-prolyl-2-(1,1-dimethylallyl)-D-tryptophan anhydride (58150-21-3)

Guidance literature:

In 1,4-dioxane; at 60 - 65 ℃; for 1.5h;

DOI:10.1021/ja00531a061

Reference yield:

(S)-benzyloxycarbonyl-proline acid chloride (61350-60-5,61350-62-7,89705-40-8,106709-50-6) → deoxybrevianamide E (34610-68-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.255 g / diethyl ether / 1.5 h

2: hydrogen / 20percent palladium-charcoal / methanol / 1 h / 70 °C / 1520 Torr

3: 1.52 g / 2-hydroxypyridine / 1 h / 70 °C

4: sodium hydride / dimethylformamide / 1.) 1 h, room temperature, 2.) 6 h, 55-60 deg C

5: 58.8 percent / magnesium chloride hexahydrate / dimethylsulfoxide / 2.5 h / 130 - 140 °C

With 2-hydroxypyridin; hydrogen; sodium hydride; magnesium chloride; palladium on activated charcoal; In methanol; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1039/P19810000959

upstream raw materials:

3-<2-(N-benzyloxycarbonyl-L-prolylamido)-2-ethoxycarbonylethyl>-2-(1,1-dimethylallyl)-indole

(S)-3-[2-(1,1-Dimethyl-allyl)-1H-indol-3-ylmethyl]-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazine-3-carboxylic acid

methyl 3-<2-(1,1-dimethylallyl)indol-3-ylmethyl>-1,4-dioxoperhydropyrrolo<1,2-a>pyrazine-3-carboxylate

(S)-3-[2-(1,1-Dimethyl-allyl)-1H-indol-3-yl]-2-[((S)-pyrrolidine-2-carbonyl)-amino]-propionic acid methyl ester

Downstream raw materials:

C₂₁H₂₅N₃O₃

brevianamide E

Refernces

• 1、 Ding, Yousong,Wet, Jeffrey R. De,Cavalcoli, James,Li, Shengying,Greshock, Thomas J.,Miller, Kenneth A.,Finefield, Jennifer M.,Sunderhaus, James D.,McAfoos, Timothy J.,Tsukamoto, Sachiko,Williams, Robert M.,Sherman, David H.. "Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived aspergillus sp.". . p. 12733 - 12740. Retrieved 2010.
• 2、 Liao, Ge,Mai, Peter,Fan, Jie,Zocher, Georg,Stehle, Thilo,Li, Shu-Ming. "Complete Decoration of the Indolyl Residue in cyclo- l -Trp- l -Trp with Geranyl Moieties by Using Engineered Dimethylallyl Transferases". . p. 7201 - 7205. Retrieved 2018.