349120-98-5

Basic information

• Product Name: N-[4-(Benzyloxy)phenyl]-2-bromoacetamide
• Synonyms: N-[4-(Benzyloxy)phenyl]-2-bromoacetamide
• CAS NO: 349120-98-5
• Molecular Formula: C₁₅H₁₄BrNO₂
• Molecular Weight: 320.18116
• Mol File: 349120-98-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-[4-(Benzyloxy)phenyl]-2-bromoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-(Benzyloxy)phenyl]-2-bromoacetamide(349120-98-5)
• EPA Substance Registry System: N-[4-(Benzyloxy)phenyl]-2-bromoacetamide(349120-98-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 349120-98-5(Hazardous Substances Data)

Upstream product

• 1145-76-2 benzyl 4-nitrophenyl ether 
• 100-51-6 benzyl alcohol 
• 350-46-9 4-Fluoronitrobenzene 
• 6373-46-2 p-benzyloxyaniline 
• 79-08-3 bromoacetic acid 

Relevant articles and documents

Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors

Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42?nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of α-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases.

Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus

The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.