73863-44-2

Usage

Uses

Used in Pharmaceutical Research:
4-CHLORO-N-(3-METHYLPHENYL)BUTANAMIDE is used as a research compound for its potential pharmacological activities. It may contribute to the development of new drugs or therapies, given its unique chemical structure and properties.
Used in Agriculture:
While not explicitly mentioned in the provided materials, 4-CHLORO-N-(3-METHYLPHENYL)BUTANAMIDE may have applications in agriculture, potentially serving as a component in the development of new pesticides or herbicides, due to its chemical structure.
Used in Materials Science:
Similarly, the compound may also find use in materials science, where its unique properties could be leveraged to create new materials or improve existing ones. However, further research and testing are likely needed to fully understand the properties and potential uses of 4-CHLORO-N-(3-METHYLPHENYL)BUTANAMIDE in this field.

InChI:InChI=1/C11H14ClNO/c1-9-4-2-5-10(8-9)13-11(14)6-3-7-12/h2,4-5,8H,3,6-7H2,1H3,(H,13,14)

Upstream product

• 108-44-1 1-amino-3-methylbenzene 
• 4635-59-0 4-Chlorobutanoyl chloride 

Downstream Products

• 186667-93-6 diethyl [1-(4-methylphenyl)pyrrolidin-2-ylidene]malonate 
• 58973-35-6 N-(4-methylphenyl)pyrrolidine-2-thione 
• 186667-92-5 diethyl [1-(3-methylphenyl)pyrrolidin-2-ylidene]malonate 
• 186667-87-8 N-(3-methylphenyl)pyrrolidine-2-thione 
• 3063-79-4 N-(4-methylphenyl)-2-pyrrolidinone 
• 24059-72-1 1-(3-methylphenyl)-pyrrolidin-2-one 
• 73863-50-0 2-chloro-3-(2-chloro-ethyl)-7-methyl-quinoline 

Relevant academic research and scientific papers

Synthesis, molecular docking, dynamic simulations, kinetic mechanism, cytotoxicity evaluation of N-(substituted-phenyl)-4-{(4-[(E)-3-phenyl-2-propenyl]-1-piperazinyl} butanamides as tyrosinase and melanin inhibitors: In vitro, in vivo and in silico approaches

In the current research work, different N-(substituted-phenyl)-4-{(4-[(E)-3-phenyl-2-propenyl]-1-piperazinyl}butanamides have been synthesized according to the protocol described in scheme 1. The synthesis was initiated by reacting various substituted anilines (1a-e) with 4-chlorobutanoyl chloride (2) in aqueous basic medium to give various electrophiles, 4-chloro-N-(substituted-phenyl)butanamides (3a-e). These electrophiles were then coupled with 1-[(E)-3-phenyl-2-propenyl]piperazine (4) in polar aprotic medium to attain the targeted N-(substituted-phenyl)-4-{(4-[(E)-3-phenyl-2-propenyl]-1-piperazinyl}butanamides (5a-e). The structures of all derivatives were identified and characterized by proton-nuclear magnetic resonance (1H NMR), carbon-nuclear magnetic resonance (13C NMR) and Infra-Red (IR) spectral data along with CHN analysis. The in vitro inhibitory potential of these butanamides was evaluated against Mushroom tyrosinase, whereby all compounds were found to be biologically active. Among them, 5b exhibited highest inhibitory potential with IC50 value of 0.013 ± 0.001 μM. The same compound 5b was also assayed through in vivo approach, and it was explored that it significantly reduced the pigments in zebrafish. The in silico studies were also in agreement with aforesaid results. Moreover, these molecules were profiled for their cytotoxicity through hemolytic activity, and it was found that except 5e, all other compounds showed minimal toxicity. The compound 5a also exhibited comparable results. Hence, some of these compounds might be worthy candidates for the formulation and development of depigmentation drugs with minimum side effects.

Novel indole based hybrid oxadiazole scaffolds with: N -(substituted-phenyl)butanamides: Synthesis, lineweaver-burk plot evaluation and binding analysis of potent urease inhibitors

In the study presented herein, 4-(1H-indol-3-yl)butanoic acid (1) was sequentially transformed in the first phase into ethyl 4-(1H-indol-3-yl)butanoate (2), 4-(1H-indol-3-yl)butanohydrazide (3) and 5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazole-2-thiol (4)

Reformatsky reactions with N-arylpyrrolidine-2-thiones: Synthesis of tricyclic analogues of quinolone antibacterial agents

A convenient synthesis of 5-oxo-1,2,3,5-tetrahydropyrrolo[1,2-α]quinoline-4-carboxylic acids, tricylic analogues of the quinolone antibiotics, is described. Key steps in the route are a novel zinc-mediated Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thione 18, and cyclisation of the resulting diethyl pyrrolidinylidenemalonate intermediates 19 in polyphosphoric acid. The products proved to be devoid of biological activity.

A versatile synthesis of tricyclic analogues of quinolone antibacterial agents: Use of a novel Reformatsky reaction

A simple synthesis of tricyclic analogues of the quinolone antibiotics bearing a diverse range of substituents on the aromatic ring is described. The key steps involve unprecedented Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thiones 8, followed by cyclisation of the resulting enaminone intermediates 9 in polyphosphoric acid.

A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 8. Conversion of Anilides into 3-Substituted Quinolines and into Quinoxalines

Anilides (4) (ArNHCOCH2R) are readily converted into 2-chloro-3-R-quinolines (5) under Vilsmeier conditions and the 3-chloro-group may be removed with zinc and acetic acid yielding 3-substituted quinolines (7).When N-nitrosodialkylamines are used in place of dimethylformamide as the Vilsmeier agent, the anilides are converted into 2-chloroquinoxalines in low yields.Several by-products are formed and the mechanisms have been explored.Thus, the formation of ethyl N-arylcarbamate from the corresponding propionanilide is shown to involve an C->O alkyl migration related to a Wolff rearrangement, while N-arylformimidoyl dichloride (18), nitriles, and isocyanides are derived from C-C cleavage of the substituted side-chain.Variation of the acid chloride component of the Vilsmeier reagent or of the solvent was generally unproductive though use of phosphoryl bromide instead of the chloride caused conversion of anilides into bromoquinolines in low yields.