Piperafizine A

Base Information

• Chemical Name: Piperafizine A
• CAS No.: 130603-59-7
• Molecular Formula: C19H16 N2 O2
• Molecular Weight: 304.348
• ChEMBL ID: CHEMBL3633234
• Mol file: 130603-59-7.mol

Synonyms:3,6-dibenzylidene-1-methyl-2,5-dioxopiperazine;piperafizine A

Chemical Property of Piperafizine A

Chemical Property:

• Vapor Pressure: 5.74E-15mmHg at 25°C
• Boiling Point: 613.1°Cat760mmHg
• Flash Point: 324.6°C
• PSA: 54.86000
• Density: 1.257g/cm³
• LogP: 0.73120
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 304.121177757
• Heavy Atom Count: 23
• Complexity: 524

Purity/Quality:

98%Min ^*data from raw suppliers

PiperafizineA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CC2=CC=CC=C2)C(=O)NC(=CC3=CC=CC=C3)C1=O
• Isomeric SMILES: CN1/C(=C\C2=CC=CC=C2)/C(=O)N/C(=C\C3=CC=CC=C3)/C1=O
• Uses: Piperafizine A is a methylated diketopiperazine formed by the condensation of phenylalanine, produced by a number of species in the Streptomyces genus. Piperafizine A exhibits little activity in vitro but potentiates vincristine antitumour potency. The mechanism of action has not been characterised. Piperafizine A is a methylated diketopiperazine.

Technology Process of Piperafizine A

There total 6 articles about Piperafizine A 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%

benzaldehyde (100-52-7) + (Z)-1-acetyl-3-benzylidene-4-methylpiperazine-2,5-dione (80687-66-7) → 3,6-dibenzylidene-1-methyl-2,5-piperazinedione (130603-59-7)

Guidance literature:

With potassium tert-butylate;

DOI:10.1246/cl.1986.1453

Reference yield: 68.0%

→ 3,6-dibenzylidene-1-methyl-2,5-piperazinedione (130603-59-7)

Guidance literature:

Reference yield: 47.0%

N,N'-diacetylpiperazin-2,5-dione (3027-05-2) + benzaldehyde (100-52-7) + methyl iodide (74-88-4) → 3,6-dibenzylidene-1-methyl-2,5-piperazinedione (130603-59-7)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at -10 - 95 ℃; chemoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2015.12.073

upstream raw materials:

benzaldehyde

(Z)-1-acetyl-3-benzylidene-4-methylpiperazine-2,5-dione

1-acetyl-3-[(Z)-benzylidene]-2,5-piperazinedione

N,N'-diacetylpiperazin-2,5-dione

Downstream raw materials:

3-(Bromo-phenyl-methyl)-3-methoxy-1-methyl-6-[1-phenyl-meth-(Z)-ylidene]-piperazine-2,5-dione

6-benzylidene-3-α-bromobenzyl-3-hydroxy-1-methyl-2,5-piperazinedione

3,6-dibenzyl-6-hydroxy-3-methoxy-1-methyl-2,5-piperazinedione

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