24942-06-1

Basic information

• Product Name: N-(4-BroMo-benzyl)-2-chloro-acetaMide
• Synonyms: N-(4-BroMo-benzyl)-2-chloro-acetaMide;N-[(4-bromophenyl)methyl]-2-chloroacetamide
• CAS NO: 24942-06-1
• Molecular Formula: C₉H₉BrClNO
• Molecular Weight: 262.53086
• Mol File: 24942-06-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 426.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.524±0.06 g/cm3(Predicted)
• PKA: 13.39±0.46(Predicted)
• CAS DataBase Reference: N-(4-BroMo-benzyl)-2-chloro-acetaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-BroMo-benzyl)-2-chloro-acetaMide(24942-06-1)
• EPA Substance Registry System: N-(4-BroMo-benzyl)-2-chloro-acetaMide(24942-06-1)

Safety Data

• Hazardous Substances Data: 24942-06-1(Hazardous Substances Data)

Upstream product

• 873-75-6 4-bromobenzenemethanol 
• 107-14-2 chloroacetonitrile 
• 3959-07-7 4-Bromobenzylamine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 849238-63-7 1-((4-bromophenyl)methylcarbamoylmethyl)-4,7,10-tris(tret-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane 

Relevant articles and documents

Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study

Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.

Preparation method for morpholine derivative

The invention especially relates to a preparation method for a morpholine derivative, i.e., N-(4-bromobenzyl)-2-morpholineethylamine, belonging to the field of organic synthesis. According to the method, 4-bromobenzylamine is used as a starting raw material and subjected to acylation, nucleophilic substitution and reduction so as to prepare the morpholine derivative. The prepared morpholine derivative can enrich organic-synthesis molecule building blocks.

Discovery, synthesis and biological evaluation of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) as novel sphingomyelin synthase 1 inhibitors

Sphingomyelin synthase (SMS) has been proved to be a potential drug target for the treatment of atherosclerosis. However, few SMS inhibitors have been reported. In this paper, structure-based virtual screening was performed on hSMS1. SAPA 1a was discovered as a novel SMS1 inhibitor with an IC50 value of 5.2 μM in enzymatic assay. A series of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) were synthesized and their biological activities toward SMS1 were evaluated. Among them, SAPA 1j was found to be the most potent SMS1 inhibitor with an IC50 value of 2.1 μM in in vitro assay. The molecular docking studies suggested the interaction modes of SMS1 inhibitors and PC with the active site of SMS1. Site-directed mutagenesis validated the involvement of residues Arg342 and Tyr338 in enzymatic sphingomyelin production. The discovery of SAPA derivatives as a novel class of SMS1 inhibitors would advance the development of more effective SMS1 inhibitors.