CALPAIN INHIBITOR XII

Base Information

• Chemical Name: CALPAIN INHIBITOR XII
• CAS No.: 181769-57-3
• Molecular Formula: C19H23N3O3
• Molecular Weight: 341.4
• Mol file: 181769-57-3.mol

Synonyms:Z-L-NVA-CONH-CH2-2-PY;CALPAIN INHIBITOR XII

Chemical Property of CALPAIN INHIBITOR XII

Chemical Property:

• PKA: 10.58±0.46(Predicted)
• PSA: 126.49000
• Density: 1.167±0.06 g/cm3(Predicted)
• LogP: 4.06560
• Solubility.: ≤16mg/ml in ethanol;16mg/ml in DMSO;20mg/ml in dimethyl formamide

Purity/Quality:

99% ^*data from raw suppliers

(Rac)-CalpainInhibitorXII ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Calpain inhibitor XII is a reversible and selective inhibitor of calpain I (μ-calpain, Ki = 19 nM), with lower affinities for calpain II (m-calpain, Ki = 120 nM) and cathepsin B (Ki = 750 nM). Calpain inhibitors, including CALPAIN INHIBITOR XII, have been used to study the role of calpains in diverse processes, including neutrophil chemotaxis, neuronal signaling, and cardiac response to injury.
• Uses: A cell-permeable dipeptidyl -ketoamide compound that acts as a potent, selective, reversible, and active site inhibitor of calpain-1

Technology Process of CALPAIN INHIBITOR XII

There total 9 articles about CALPAIN INHIBITOR XII 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: 50.0%

2-(Aminomethyl)pyridine (3731-51-9) + 2-[1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-butyl]-[1,3]dithiolane-2-carboxylic acid ethyl ester → {(S)-3-Methyl-1-[1-(pyridin-2-ylmethyl)-aminooxalyl]-butylcarbamoyl}-butyl)-carbamic acid benzyl ester (181769-57-3)

Guidance literature:

In ethanol; Ambient temperature;

DOI:10.1021/jm950541c

Reference yield:

Z-Leu-OH (2018-66-8) → {(S)-3-Methyl-1-[1-(pyridin-2-ylmethyl)-aminooxalyl]-butylcarbamoyl}-butyl)-carbamic acid benzyl ester (181769-57-3)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N, dicyclohexylcarbodiimide, 1-hydroxybenzotriazole / dimethylformamide / 16.5 h / Ambient temperature

2: NaOH / methanol / 3 h / Ambient temperature

3: pyridine, 4-N,N-dimethylaminopyridine / tetrahydrofuran

4: NaOEt / ethanol

5: BF₃*OEt₂ / CH₂Cl₂

6: 50 percent / ethanol / Ambient temperature

With pyridine; dmap; sodium hydroxide; boron trifluoride diethyl etherate; sodium ethanolate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm950541c

Reference yield:

N-benzyloxycarbonyl-L-leucine methyl ester (51021-87-5) → {(S)-3-Methyl-1-[1-(pyridin-2-ylmethyl)-aminooxalyl]-butylcarbamoyl}-butyl)-carbamic acid benzyl ester (181769-57-3)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOH / methanol / 3 h / Ambient temperature

2: Et₃N, dicyclohexylcarbodiimide, 1-hydroxybenzotriazole / dimethylformamide / 16.5 h / Ambient temperature

3: NaOH / methanol / 3 h / Ambient temperature

4: pyridine, 4-N,N-dimethylaminopyridine / tetrahydrofuran

5: NaOEt / ethanol

6: BF₃*OEt₂ / CH₂Cl₂

7: 50 percent / ethanol / Ambient temperature

With pyridine; dmap; sodium hydroxide; boron trifluoride diethyl etherate; sodium ethanolate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm950541c

upstream raw materials:

2-(Aminomethyl)pyridine

Z-Leu-OH

N-benzyloxycarbonyl-L-leucine methyl ester

benzyl carbonochloridate

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