2,6-Piperazinedione, 4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-, rel-

Base Information

• Chemical Name: 2,6-Piperazinedione, 4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-, rel-
• CAS No.: 21416-88-6
• Molecular Formula: C₁₂H₁₈N₄O₄
• Molecular Weight: 282.299
• European Community (EC) Number: 633-641-5
• DSSTox Substance ID: DTXSID201259810
• Nikkaji Number: J691.670H
• Wikipedia: ICRF_193
• Wikidata: Q5969732
• ChEMBL ID: CHEMBL264684
• Mol file: 21416-88-6.mol

Synonyms:4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-2,6-piperazinedione;ICRF 193;ICRF-193

Chemical Property of 2,6-Piperazinedione, 4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-, rel-

Chemical Property:

• Vapor Pressure: 3.48E-11mmHg at 25°C
• Boiling Point: 526.7°Cat760mmHg
• Flash Point: 272.4°C
• PSA: 105.80000
• Density: 1.308g/cm³
• LogP: -1.89220
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble4mg/mL
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 282.13280507
• Heavy Atom Count: 20
• Complexity: 390

Purity/Quality:

98%,99%, ^*data from raw suppliers

ICRF-193 apoptosis inducer, arabinosidase substrate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(C)N1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2
• Isomeric SMILES: C[C@H]([C@H](C)N1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2
• Uses: ICRF-193 has been used as a topoisomerase II (TOP2) inhibitor to treat mouse oocytes to investigate the role of TOP2 in meiosis.

Technology Process of 2,6-Piperazinedione, 4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-, rel-

There total 13 articles about 2,6-Piperazinedione, 4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-, rel- 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: 80.0%

tetramethyl meso-2,3-diaminobutane-N,N,N',N'-tetraacetate → ICRF-193 (21416-88-6)

Guidance literature:

With sodium hydride; formamide; In 1,4-dioxane; at 20 ℃; for 36h;

DOI:10.1016/0006-2952(96)00305-X

Reference yield: 57.0%

tetramethyl 2(S),3(S)-diaminobutane-N,N,N',N'-tetraacetate → 2(S),3(S)-bis(2,6-dioxopiperazin-4-yl)butane (21416-88-6)

Guidance literature:

With sodium hydride; formamide; In 1,4-dioxane; at 20 ℃; for 36h;

DOI:10.1016/0006-2952(96)00305-X

Reference yield: 55.0%

meso-tetramethyl 2,3-diaminobutane-N,N,N',N'-tetraacetate → meso-2,3-bis(3,5-dioxopiperazine-1-yl)butane (21416-88-6)

Guidance literature:

meso-tetramethyl 2,3-diaminobutane-N,N,N',N'-tetraacetate; With sodium hydride; formamide; In 1,4-dioxane; mineral oil; at 10 - 20 ℃; for 24h; Inert atmosphere;

With hydrogenchloride; In water; pH=4 - 5;

DOI:10.1021/acs.jmedchem.0c02157

Downstream raw materials:

2,3-bis(4-morpholinomethyl-3,5-dioxopiperazin-1-yl)butane