1140908-89-9

Basic information

• Product Name: (alphaS)-alpha-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine methyl ester
• Synonyms: (alphaS)-alpha-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine methyl ester;L-Phenylalanine, (αS)-α-[[2-(4-Morpholinyl)acetyl]aMino]benzenebutanoyl-L-leucyl-, Methyl ester;methyl ((S)-2-(2-morpholinoacetamido)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate
• CAS NO: 1140908-89-9
• Molecular Formula: C32H44N4O6
• Molecular Weight: 580.72
• Mol File: 1140908-89-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (alphaS)-alpha-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (alphaS)-alpha-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine methyl ester(1140908-89-9)
• EPA Substance Registry System: (alphaS)-alpha-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine methyl ester(1140908-89-9)

Safety Data

• Hazardous Substances Data: 1140908-89-9(Hazardous Substances Data)

Usage

Uses

(S)-Methyl 2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoate is a derivative of Carfilzomib (C183460), which is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 3235-69-6 morpholin-4-ylacetic acid 
• 868539-99-5 C₂HF₃O₂*C₂₆H₃₅N₃O₄ 
• 63-91-2 L-phenylalanine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 61-90-5 L-leucine 
• 89531-58-8 N-(carboxymethyl)morpholine hydrochloride 
• 82732-07-8 Boc-L-homophenylalanine 
• 6461-07-0 methyl (S)-2-[(S)-2-amino-4-methylpentanamido]-3-phenylpropanoate hydrochloride 
• 868539-96-2 (S)-methyl 2-((S)-2-tert.butoxycarbonyIamino-4-phenylbutanamido-4-methylpentanamido)-3-phenylpropanoate 
• 15136-32-0 (N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 110-91-8 morpholine 

Relevant articles and documents

Preparation and biological evaluation of soluble tetrapeptide epoxyketone proteasome inhibitors

A series of novel tetrapeptidyl epoxyketone inhibitors of 20S proteasome was designed and synthesized. To fully understand the SAR, various groups at R1, R2, R3, R4 and R5 positions, including aromatic and aliphatic substituents were designed, synthesized and biologically assayed. Based on the enzymatic results, seven compounds were selected to evaluate their cellular activities and soluble compound 36 showed strong potency against human multiple myeloma (MM) cell lines. Microsomal stability results indicated that compound 36 was more stable in mice, rat and human microsomes than marketed carfilzomib. The in vivo activities of this compound were evaluated with the xenograft mice models of MM cell lines ARH77 and RPMI-8226 with luciferase expression and the T/C value of the two models were 49.5% and 37.6%, respectively. To evaluate the potential cardiovascular toxicity, inhibition of hERG ion channel in HEK293 cells by compound 36 and carfilzomib was carried out. The results indicated that 36 had no binding affinity for the hERG ion channel while carfilzomib could bind it with IC50 of 92.1 μM.

CRYSTALLINE PEPTIDE EPOXY KETONE PROTEASE INHIBITORS AND THE SYNTHESIS OF AMINO ACID KETO-EPOXIDES

The invention relates to crystalline peptide keto epoxide compounds, methods of their preparation, and related pharmaceutical compositions. This invention also relates to methods for the preparation of amino acid keto-epoxides. Specifically, allylic ketones are stereoselectively converted to the desired keto epoxides.