2-[[[2-(4-Benzylpiperazin-1-ium-1-yl)acetyl]hydrazinylidene]methyl]-6-prop-2-enylphenolate

Base Information

• Chemical Name: 2-[[[2-(4-Benzylpiperazin-1-ium-1-yl)acetyl]hydrazinylidene]methyl]-6-prop-2-enylphenolate
• CAS No.: 315183-21-2
• Molecular Formula: C23H28 N4 O2
• Molecular Weight: 392.501
• Hs Code.: 29335990
• Mol file: 315183-21-2.mol

Synonyms:

Chemical Property of 2-[[[2-(4-Benzylpiperazin-1-ium-1-yl)acetyl]hydrazinylidene]methyl]-6-prop-2-enylphenolate

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 8.82±0.40(Predicted)
• Flash Point: °C
• PSA: 68.17000
• Density: g/cm³
• LogP: 2.65530
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 392.22122615
• Heavy Atom Count: 29
• Complexity: 539

Purity/Quality:

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

PAC 1 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-50/53
• Safety Statements: 26-36/37-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCC1=C(C(=CC=C1)C=NNC(=O)C[NH+]2CCN(CC2)CC3=CC=CC=C3)[O-]
• Description: PAC-1 (315183-21-2) is a procaspase-activating compound, directly activating procaspase-3, producing caspase-3, EC50=0.22 μM.1 It is less potent at activating procaspase-7, EC50=4.5 μM. It induces apoptosis in a variety of cancer cell lines. The mechanism of activation involves sequestering inhibitory zinc ions thus allowing procaspase-3 to autoactivate.2?? Sensitizes cancer cells to various chemotherapeutic agents.3
• Uses: PAC-1 is a potent procaspase-3 activator with EC50 of 0.22 μM.

Technology Process of 2-[[[2-(4-Benzylpiperazin-1-ium-1-yl)acetyl]hydrazinylidene]methyl]-6-prop-2-enylphenolate

There total 6 articles about 2-[[[2-(4-Benzylpiperazin-1-ium-1-yl)acetyl]hydrazinylidene]methyl]-6-prop-2-enylphenolate 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: 95.0%

3-allylsalicylaldehyde (24019-66-7) + 2-(4-benzylpiperazin-1-yl)acetohydrazide (24632-70-0) → 2-(4-benzylpiperazin-1-yl)-N-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]acetamide (315183-21-2,1044929-62-5)

Guidance literature:

With hydrogenchloride; In ethanol;

Reference yield:

salicylaldehyde (90-02-8) → 2-(4-benzylpiperazin-1-yl)-N-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]acetamide (315183-21-2,1044929-62-5)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide

2: neat (no solvent) / 200 °C

3: hydrogenchloride / water / Reflux

With hydrogenchloride; potassium carbonate; In water; N,N-dimethyl-formamide; 2: |Claisen Rearrangement;

DOI:10.1021/acs.jmedchem.5b00413

Reference yield:

2-(allyloxy)benzaldehyde (28752-82-1) → 2-(4-benzylpiperazin-1-yl)-N-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]acetamide (315183-21-2,1044929-62-5)

Guidance literature:

Multi-step reaction with 2 steps

1: neat (no solvent) / 200 °C

2: hydrogenchloride / water / Reflux

With hydrogenchloride; In water; 1: |Claisen Rearrangement;

DOI:10.1021/acs.jmedchem.5b00413

upstream raw materials:

3-allylsalicylaldehyde

2-(4-benzylpiperazin-1-yl)acetohydrazide

salicylaldehyde

2-(allyloxy)benzaldehyde

Downstream raw materials:

N'-(3-allyl-2-hydroxybenzyl)-2-(4-benzylpiperazin-1-yl)acetohydrazide

Refernces

• 1、 Hsu, Danny C.,Roth, Howard S.,West, Diana C.,Botham, Rachel C.,Novotny, Chris J.,Schmid, Steven C.,Hergenrother, Paul J.. "Parallel synthesis and biological evaluation of 837 analogues of procaspase-activating compound 1 (PAC-1)". experimental part. p. 44 - 50. Retrieved 2012/03/10.
• 2、 -. "COMPOSITIONS AND METHODS INCLUDING CELL DEATH INDUCERS AND PROCASPASE ACTIVATION". Page/Page column 68. . Retrieved 2008/12/08.