1469996-55-1

Basic information

• Product Name: methyl (2S)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoate
• Synonyms: methyl (2S)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoate
• CAS NO: 1469996-55-1
• Molecular Weight: 423.896
• Mol File: 1469996-55-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl (2S)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoate(1469996-55-1)
• EPA Substance Registry System: methyl (2S)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoate(1469996-55-1)

Safety Data

• Hazardous Substances Data: 1469996-55-1(Hazardous Substances Data)

Upstream product

• 17585-69-2 L-phenylalanine hydrochloride 
• 52803-75-5 2-(benzyloxy)-5-chlorobenzoic acid 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

Downstream Products

• 1227476-97-2 C₂₂H₁₈Cl₂N₂O₃ 
• 1469996-62-0 (2S)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoic acid 
• 1469996-67-5 2-(benzyloxy)-5-chloro-N-{(2S)-1-[(4-chlorophenyl)amino]-1-oxo-3-phenylpropan-2-yl}benzamide 

Relevant articles and documents

Novel modified leucine and phenylalanine dipeptides modulate viability and attachment of cancer cells

Here, we describe the synthesis and biological characterization of 32 novel phenylalanine and leucine dipeptides modified on both the N and C termini by salicylic acid and aromatic or alicyclic amines, respectively. All compounds displayed antiproliferative activity in the tested cancer cell lines and eight of the compounds exhibited single digit micromolar GI50 values. Treated cells rapidly detached from surface of tissue culture dishes and we found that focal adhesion kinase (FAK), p130CAS and paxillin, which are important regulators of cell adhesion, were dephosphorylated at Y397, Y410 and Y118, respectively. The most potent compound reduced proliferation in the HCT-116 cell line in a dose-dependent manner, as shown by a decrease in 5-bromo-2′-deoxyuridine incorporation into DNA. Furthermore, this compound increased the levels of several apoptotic markers, including activated caspases, and increased site-specific poly-(ADP-ribose)polymerase (PARP) cleavage.

Substituted 2-hydroxy-N-(arylalkyl)benzamides induce apoptosis in cancer cell lines

Variously substituted 2-hydroxy-N-(arylalkyl)benzamides were prepared and screened for antiproliferative and cytotoxic activity in cancer cell lines in vitro. Five compounds, out of 33 showed single-digit micromolar IC50 values against several human cancer cell lines. One of the most potent compounds N-((R)-1-(4-chlorophenylcarbamoyl)-2-phenylethyl)-5-chloro-2-hydroxybenzamide (6k) reduced proliferation and induced apoptosis in the melanoma cell line G361 in a dose-dependent manner, as shown by decrease in 5-bromo-2′- deoxyuridine incorporation and increase in several apoptotic markers, including subdiploid population increase, activation of caspases and site-specific poly-(ADP-ribose)polymerase (PARP) cleavage.