57339-11-4

Usage

Uses

Used in Pharmaceutical Research:
N1-(3,5-DICHLOROPHENYL)-2-BROMOACETAMIDE is used as a key intermediate for the development of potential anti-cancer and antifungal agents. Its unique structure allows for the creation of new compounds with therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Chemical Research:
In the field of chemical research, N1-(3,5-DICHLOROPHENYL)-2-BROMOACETAMIDE is utilized as a building block for the synthesis of various organic compounds. Its reactivity and structural features make it a valuable component in the exploration of new chemical reactions and molecular interactions.
Used in Molecular Interaction Studies:
N1-(3,5-DICHLOROPHENYL)-2-BROMOACETAMIDE is employed in the study of molecular interactions to understand its binding properties with biological targets. This knowledge aids in the design of more effective drugs with improved specificity and reduced side effects.
Used in the Development of New Chemical Reactions:
N1-(3,5-DICHLOROPHENYL)-2-BROMOACETAMIDE is also of interest in the development of innovative chemical reactions, where its unique functional groups can participate in novel synthetic pathways, expanding the scope of organic synthesis.

InChI:InChI=1/C8H6BrCl2NO/c9-4-8(13)12-7-2-5(10)1-6(11)3-7/h1-3H,4H2,(H,12,13)

Upstream product

• 598-21-0 2-Bromoacetyl bromide 
• 626-43-7 3,5-Dichloroaniline 
• 22118-09-8 2-bromoacetyl chloride 

Downstream Products

• 868631-64-5 2-chloro-N-[1-(3'-cyano-biphenyl-4-yl)-ethyl]-N-[(3,5-dichloro-phenylcarbamoyl)-methyl]-acetamide 
• 868631-65-6 2-chloro-N-[1-(3'-cyano-biphenyl-4-yl)-ethyl]-N-[(3,5-dichloro-phenylcarbamoyl)-methyl]-acetamide 
• 885315-76-4 2-chloro-N-(3'-cyano-biphenyl-4-ylmethyl)-N-[(3,5-dichloro-phenylcarbamoyl)-methyl]-acetamide 
• 885315-81-1 3-chloro-N-(3'-cyano-biphenyl-4-ylmethyl)-N-[(3,5-dichloro-phenylcarbamoyl)-methyl]-propionamide 
• 868631-63-4 2-chloro-N-[2-(3'-cyano-biphenyl-4-yl)-ethyl]-N-[(3,5-dichloro-phenylcarbamoyl)-methyl]-acetamide 
• 868631-67-8 3-chloro-N-[1-(3'-cyano-biphenyl-4-yl)-ethyl]-N-[(3,5-dichloro-phenylcarbamoyl)-methyl]-propionamide 
• 868631-68-9 3-chloro-N-[1-(3'-cyano-biphenyl-4-yl)-ethyl]-N-[(3,5-dichloro-phenylcarbamoyl)-methyl]-propionamide 
• 885315-93-5 3-chloro-N-[2-(3'-cyano-biphenyl-4-yl)-ethyl]-N-[(3,5-dichloro-phenylcarbamoyl)-methyl]-propionamide 
• 1090383-87-1 C₂₀H₂₃Cl₂N₃O 

Relevant academic research and scientific papers

AUTOTAXIN INHIBITOR COMPOUNDS

Described herein are compounds that are autotaxin inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with autotaxin activity.

Synthesis and cytotoxicity of thieno[2,3-b]pyridine and furo[2,3-b]pyridine derivatives

Forty seven thieno[2,3-b]pyridines-2-carboxamides, furo[2,3-b]pyridines-2-carboxamides and tetrahydrothieno[2,3-b]quinolones-2-carboxamides derivatives were synthesized and tested for their antiproliferative activity against the NCI-60 cell lines. The 5-keto-tetrahydrothieno[2,3-b]quinolones-2-carboxamides (series 17) were found to have the greatest activity, with the compound containing a 3-methoxyphenylcarboxamide (compound 17d) being the most active, with GI50values in the low nanomolar range against a range of cell lines, in particular the melanoma cell line MDA-MD-435 (GI50- 23 nM) and the breast cancer cell line MDA-MB-468 (GI50- 46 nM). Molecular modelling of series 17 against phosphoinositide specific-phospholipase C reveals that the side chains of the amino acids His356, Glu341, Arg549 and Lys438 are involved in hydrogen bonding with the ligands as well as a lipophilic pocket is occupied by the phenyl carboxamide moiety.

The design and synthesis of 1,4-substituted piperazine derivatives as triple reuptake inhibitors

Novel 1,4-substituted piperazine derivatives 5, Series A and B were designed by fragment analysis and molecular modification of 4 selected piperazine-containing compounds which possess antidepressant activity. We synthesized new 39 analogues of Series A and 10 compounds of Series B, respectively. The antidepressant screening against DA, NE, and serotonin neurotransmitter uptake inhibition was carried out using the Neurotransmitter Transporter Uptake Assay Kit. The compounds in Series B showed relatively higher reuptake inhibitory activity for SERT, NET, and DAT than those in Series A. The length of spacer between the central piperazine core and the terminal phenyl ring substituted at the piperazine ring in Series B seems to exert an important role in the activity.

Discovery of 3-methyl-N-(1-oxy-3′,4′,5′,6′- tetrahydro-2′H-[2,4′-bipyridine]-1′-ylmethyl)benzamide (ABT-670), an orally bioavailable dopamine D4 agonist for the treatment of erectile dysfunction

The goal of this study was to identify a structurally distinct D4-selective agonist with superior oral bioavailability to our first-generation clinical candidate 1a (ABT-724) for the potential treatment of erectile dysfunction. Arylpiperazines such as (heteroarylmethyl)piperazine 1a, benzamide 2, and acetamides such as 3a,b exhibit poor oral bioavailability. Structure-activity relationship (SAR) studies with the arylpiperidine template provided potent partial agonists such as 4d and 5k that demonstrated no improvement in oral bioavailability. Further optimization with the (N-oxy-2-pyridinyl)piperidine template led to the discovery of compound 6b (ABT-670), which exhibited excellent oral bioavailability in rat, dog, and monkey (68%, 85%, and 91%, respectively) with comparable efficacy, safety, and tolerability to 1a. The N-oxy-2-pyridinyl moiety not only provided the structural motif required for agonist function but also reduced metabolism rates. The SAR study leading to the discovery of 6b is described herein.