Z-L-Phe chloromethyl ketone

Base Information

• Chemical Name: Z-L-Phe chloromethyl ketone
• CAS No.: 26049-94-5
• Molecular Formula: C18H18ClNO3
• Molecular Weight: 331.799
• Hs Code.: 29225000
• European Community (EC) Number: 423-660-5,247-432-8
• DSSTox Substance ID: DTXSID90885328
• Nikkaji Number: J150.083J
• Wikidata: Q27467643
• Pharos Ligand ID: 58RCR58N3YC4
• ChEMBL ID: CHEMBL303579
• Mol file: 26049-94-5.mol

Synonyms:benzyloxycarbonylphenylalanine chloromethyl ketone;ZPCK

Chemical Property of Z-L-Phe chloromethyl ketone

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.99E-10mmHg at 25°C
• Melting Point: 107-108 °C(lit.)
• Refractive Index: 1.573
• Boiling Point: 503.1 °C at 760 mmHg
• PKA: 10.74±0.46(Predicted)
• Flash Point: 258.1 °C
• PSA: 55.40000
• Density: 1.228 g/cm³
• LogP: 3.72290
• Storage Temp.: -15°C
• Solubility.: Soluble in DMSO (up to 50 mg/ml) or in Ethanol (up to 15 mg/ml with warming).
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 331.0975211
• Heavy Atom Count: 23
• Complexity: 377

Purity/Quality:

99% ^*data from raw suppliers

SL01 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)CCl)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)CCl)NC(=O)OCC2=CC=CC=C2
• Description: SL-01 (26049-94-5) inhibits the p53-MDM2 interaction (20 μM). Has also been shown to inhibit bovine chymotrypsin A-γ.
• Uses: ZPCK's a peptidase from baker's yeast,and it is with esterase activities of carboxypeptidase Y. SL 01 is a prodrug of gemcitabine , the nucleoside analog used intravenously to treat various cancers that was designed for improved oral bioavailability. SL 01 can inhibit the growth of human non-small cell lung cancer NCI-H460 cells, colon cancer HCT-116 cells, and breast cancer MCF-7 cells (IC50s = 0.78, 0.92, and 0.64 μM, respectively), inducing apoptosis. In nude mice bearing NCI-H460, HCT-116, or MCF-7 cancer cell xenografts, SL 01 at 10-50 μM/kg has been shown to delay tumor growth. Enzyme inhibitor.

Technology Process of Z-L-Phe chloromethyl ketone

There total 26 articles about Z-L-Phe chloromethyl ketone 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: 83.0%

(3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride (34351-19-4) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (26049-94-5)

Guidance literature:

With sodium hydrogencarbonate; In water; toluene;

Reference yield: 83.0%

(3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride (34351-19-4) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (26049-94-5) + 2,5-dibenzyl-3-chloromethyl-6-methyl-pyrazine

Guidance literature:

With sodium hydrogencarbonate; In water; toluene; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(01)01115-7

Reference yield: 77.0%

Chloroiodomethane (593-71-5) + N-benzyloxycarbonyl-L-phenylalanine ethyl ester (28709-70-8) → (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (26049-94-5)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -75 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(97)00605-9

upstream raw materials:

diazomethane

(C₈H₇O₂)(NHCHCOO)(CH₂C₆H₅)(CO₂C₂H₅)

benzyl chloroformate

Z-Phe-O-COO-isoBu

Downstream raw materials:

5-Methoxy-5-methyl-4-[1-phenyl-meth-(E)-ylidene]-oxazolidin-2-one

2-((S)-3-Benzyloxycarbonylamino-2-oxo-4-phenyl-butyl)-malonic acid dimethyl ester

N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol

(2R,3S)-1-chloro-2-hydroxy-3-N-benzyloxycarbonylamino-4-phenylbutane

Refernces

• 1、 Maillard, Ludovic T.,Bertout, Sébastien,Quinonéro, Ophélie,Akalin, Gül?en,Turan-Zitouni, Gülhan,Fulcrand, Pierre,Demirci, Fatih,Martinez, Jean,Masurier, Nicolas. "Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives". . p. 1803 - 1807. Retrieved 2013/04/10.
• 2、 Debaene, Fran?ois,Da Silva, Julien A.,Pianowski, Zbigniew,Duran, Fernando J.,Winssinger, Nicolas. "Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases". . p. 6577 - 6586. Retrieved 2008/02/05.