2564-03-6

Basic information

• Product Name: N-(3-BROMOPHENYL)-2-CHLOROACETAMIDE
• Synonyms: AKOS B029209;AKOS BBS-00004016;BUTTPARK 80\07-91;OTAVA-BB BB7020410099;N-(3-BROMOPHENYL)-2-CHLOROACETAMIDE;N-(3-bromophenyl)-2-chloro-ethanamide;SBB016594;ZINC02167845
• CAS NO: 2564-03-6
• Molecular Formula: C₈H₇BrClNO
• Molecular Weight: 248.5
• Mol File: 2564-03-6.mol
• Article Data: 32

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(3-BROMOPHENYL)-2-CHLOROACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-BROMOPHENYL)-2-CHLOROACETAMIDE(2564-03-6)
• EPA Substance Registry System: N-(3-BROMOPHENYL)-2-CHLOROACETAMIDE(2564-03-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 2564-03-6(Hazardous Substances Data)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 591-19-5 m-Bromoaniline 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 53316-92-0 N-(3-Bromo-phenyl)-2-piperidin-1-yl-acetamide 
• 128890-30-2 N-(3-Bromo-phenyl)-2-(2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide 
• 135085-45-9 6-Benzyl-2-(3-bromophenylaminocarbonylmethyl)-s-triazolo<3.4-a>phthalazin-3-one 
• 135085-42-6 6-Benzyl-3-(3-bromophenylaminocarbonylmethylthio)-s-triazolo<3,4-a>-phthalazine 
• 215649-75-5 N-(3-Bromo-phenyl)-2-(2-hydroxy-ethylamino)-acetamide 
• 215649-81-3 1-(3-Bromo-phenyl)-piperazin-2-one; hydrochloride 
• 81112-69-8 N-(3-Bromo-phenyl)-2-piperidin-1-yl-acetamide; compound with oxalic acid 
• 133035-89-9 N-(3-Bromo-phenyl)-2-(2,2-dimethyl-2H-chromen-7-yloxy)-acetamide 
• 133035-62-8 N-(3-Bromo-phenyl)-2-(4-hydroxy-2,2-dimethyl-chroman-7-yloxy)-acetamide 
• 1236306-27-6 N-(3-bromophenyl)-2-(4-(4-(pyridin-4-ylmethyl)phthalazin-1-yl)piperazin-1-yl)acetamide 
• 1236306-43-6 N-(3-bromophenyl)-2-(4-(4-benzylphthalazin-1-yl)piperazin-1-yl)acetamide 
• 454245-56-8 2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)-N-(3-bromophenyl)acetamide 
• 56967-17-0 m-bromoaniline hydrochloride 
• 1182347-20-1 diethyl [N-(3-bromophenyl)carbamoyl]methylphosphonate 

Relevant articles and documents

Synthesis and Biological Evaluation of Dithiobisacetamides as Novel Urease Inhibitors

Thirty-eight disulfides containing N-arylacetamide were designed and synthesized in an effort to develop novel urease inhibitors. Biological evaluation revealed that some of the synthetic compounds exhibited strong inhibitory potency against both cell-free urease and urease in intact cell with low cytotoxicity to mammalian cells even at concentration up to 250 μM. Of note, 2,2′-dithiobis(N-(2-fluorophenyl)acetamide) (d7), 2,2′-dithiobis(N-(3,5-difluorophenyl)acetamide) (d24), and 2,2′-dithiobis(N-(3-fluorophenyl)acetamide) (d8) were here identified as the most active inhibitors with IC50 of 0.074, 0.44, and 0.81 μM, showing 32- to 355-fold higher potency than the positive control acetohydroxamic acid. These disulfides were confirmed to bind urease without covalent modification of the cysteine residue and to inhibit urease reversibly with a mixed inhibition mechanism. They also showed very good anti-Helicobacter pylori activities with d8 showing a comparable potency to the clinical used drug amoxicillin. The impressive in vitro biological profile indicated their immense potential as therapeutic agents to tackle H. pylori caused infections.

Naproxen based 1,3,4-oxadiazole derivatives as EGFR inhibitors: Design, synthesis, anticancer, and computational studies

A library of novel naproxen based 1,3,4-oxadiazole derivatives (8–16 and 19–26) has been synthesized and screened for cytotoxicity as EGFR inhibitors. Among the synthesized hy-brids, compound2-(4-((5-((S)-1-(2-methoxynaphthalen-6-yl)ethyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)phenol(15) was the most potent compound against MCF-7 and HepG2cancer cells with IC50 of 2.13 and 1.63 μg/mL, respectively, and was equipotent to doxorubicin (IC50 1.62 μg/mL) towards HepG2. Furthermore, compound 15 inhibited EGFR kinase with IC50 0.41 μM compared to standard drug Erlotinib (IC50 0.30 μM). The active compound induces a high percentage of necrosis towards MCF-7, HePG2 and HCT 116 cells. The docking studies, DFT and MEP also supported the biological data. These results demonstrated that these synthesized naproxen hybrids have EGFR inhibition effects and can be used as leads for cancer therapy.

Anti-melanogenesis and anti-tyrosinase properties of aryl-substituted acetamides of phenoxy methyl triazole conjugated with thiosemicarbazide: Design, synthesis and biological evaluations

A series of aryl phenoxy methyl triazole conjugated with thiosemicarbazides were designed, synthesized, and evaluated for their tyrosinase inhibitory activities in the presence of L-dopa and L-tyrosine as substrates. All the compounds showed tyrosinase inhibition in the sub-micromolar concentration. Among the derivatives, compound 9j bearing benzyl displayed exceptionally high potency against tyrosinase with IC50 value of 0.11 μM and 0.17 μM in the presence of L-tyrosine and L-dopa as substrates which is significantly lower than that of kojic acid as the positive control with an IC50 value of 9.28 μM for L-tyrosine and 9.30 μM for L-dopa. According to Lineweaver–Burk plot, 9j demonstrated an uncompetitive type of inhibition in the kinetic assay. Also, in vitro antioxidant activities determined by DPPH assay recorded an IC50 value of 68.43 μM for 9i. The melanin content of 9j was determined on B16F10 melanoma human cells which demonstrated a significant reduction of the melanin content. Moreover, the binding energies corresponding to the same ligand as well as computer-aided drug-likeness and pharmacokinetic studies were also carried out. Compound 9j also possessed metal chelation potential correlated to its high anti-TYR activity.