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

Description

(alphaS)-alpha-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine methyl ester, also known as a derivative of Carfilzomib (C183460), is a second-generation proteasome inhibitor. It is a complex organic compound with a specific structure that plays a crucial role in the inhibition of proteasomes, which are essential for cellular function and protein degradation.

Uses

Used in Pharmaceutical Industry:
(alphaS)-alpha-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine methyl ester is used as a therapeutic agent for the treatment of relapsed and refractory multiple myeloma. It functions by inhibiting the proteasome, a cellular component responsible for the degradation of proteins, thus disrupting the balance of protein synthesis and degradation in cancer cells and leading to their death.
The compound's specific structure allows it to target and inhibit the proteasome more effectively than previous generations of inhibitors, making it a valuable tool in the fight against multiple myeloma, a type of blood cancer. Its use in the pharmaceutical industry is focused on providing a more effective treatment option for patients with this disease, improving their quality of life and survival rates.

Upstream product

• 110-91-8 morpholine 
• 868540-08-3 C₂₈H₃₆ClN₃O₅ 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 15136-32-0 (N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester 
• 868539-96-2 (S)-methyl 2-((S)-2-tert.butoxycarbonyIamino-4-phenylbutanamido-4-methylpentanamido)-3-phenylpropanoate 
• 6461-07-0 methyl (S)-2-[(S)-2-amino-4-methylpentanamido]-3-phenylpropanoate hydrochloride 
• 82732-07-8 Boc-L-homophenylalanine 
• 89531-58-8 N-(carboxymethyl)morpholine hydrochloride 
• 61-90-5 L-leucine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 
• 3235-69-6 morpholin-4-ylacetic acid 
• 868539-99-5 C₂HF₃O₂*C₂₆H₃₅N₃O₄ 

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.