191168-66-8

Upstream product

• 106-49-0 p-toluidine 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 96-48-0 4-butanolide 
• 99-99-0 1-methyl-4-nitrobenzene 

Downstream Products

• 3063-79-4 N-(4-methylphenyl)-2-pyrrolidinone 
• 191168-87-3 4-Piperazin-1-yl-N-p-tolyl-butyramide 
• 919111-30-1 3-(p-tolylcarbamoyl)propyltriphenylphosphonium chloride 
• 1286232-06-1 4-azido-N-(4-methylphenyl)butyramide 
• 1159836-44-8 N-(4-methylphenyl)tetramethylenediamine 
• 186667-93-6 diethyl [1-(4-methylphenyl)pyrrolidin-2-ylidene]malonate 
• 58973-35-6 N-(4-methylphenyl)pyrrolidine-2-thione 
• 191168-75-9 4-(4-Benzyl-piperazin-1-yl)-N-p-tolyl-butyramide 

Relevant academic research and scientific papers

Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors

This manuscript describes the synthesis of some new N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides (5a-c) through a facile bi-step strategy. The structures of these compounds were corroborated by their IR, EI-MS, 1H NMR, 13C NMR spectra along with CHN analysis data. The results of Mushroom tyrosinase in vitro inhibition revealed that all compounds were superb inhibitors of this enzyme and among them 5b was identified as the most active compound having IC50 value of 0.168 ± 0.057 μM, relative to the standard (16.841 ± 1.146 μM). The kinetic analysis (Ki = 0.22 μM) of this molecule revealed that it does not competitively inhibit the tyrosinase enzyme. It also significantly reduced (P 0.001) the enormous amount of pigments to about 75.373% in an in vivo protocol, when studied on the zebrafish embryos. Moreover, the cytotoxicity of these butanamides was also profiled and it was an inferred that of these molecules possess very mild cytotoxicity. So, it was consummated from the present investigation that these compounds might be utilized as less cytotoxic therapeutic agents for the betterment of skin related ailments.

Organotin-catalyzed synthesis of hydroxyalkylamides from lactones via a ring-opening process

A new strategy for the facile synthesis of hydroxyalkylamides through the ring-opening reaction of lactone with amine promoted by dibutyltin acetate was developed. A series of hydroxyalkylamide compounds were obtained and the method was successfully applied to the synthesis of pharmaceutically active molecules tyrosinase inhibitor V and HDAC inhibitor VI via a three-step synthetic pathway. The broad substrate scope, mild reaction conditions and practical application proved the effectiveness, compatibility and practicality of this method.

A one pot protocol to convert nitro-arenes into: N-aryl amides

A two-step one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the methodology was applied to the reaction with γ-butyrolactone, the desired N-aryl butanamide derivative was obtained, featuring a chlorine atom at the γ-position, a functionalized handle that can be used for further synthetic manipulation of the reaction product. Such an intermediate has already been employed as a key advanced precursor of pharmaceutically active compounds.

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)

New synthetic routes for N-substituted 1,n-diamines. II. Synthesis of selectively N-substituted tetra- and pentamethylenediamines from ω-alkanoic acid derivatives

A new approach for the synthesis of selectively N-substituted tetra- and pentamethylenediamines 1 (n = 4,5) is described. The method uses N-substituted ω-haloalkanamides 2 as precursors and involves the microwave-promoted conversion into ω-azidocarboxamides 3 and later the reduction of both azido and carboxamide groups with diborane.

Anticancer activities of some arylcarbamoylalkyltriphenylphosphonium chlorides

A series of novel arylcarbamoylalkyltriphenylphosphonium chlorides were synthesized. The newly synthesized compounds, [R-(p-C6H 4)-NH-CO-R1P⊕(C6H 4)3]Clθ, R = H (2), CH3 (4), NO2 (6), R1 = -CH2- (b), CH3CH2CH2- (c), -CH2CH2CH 2 (d), the analogs of an anticancer drug, were characterized by infrared (IR), 1H nuclear magnetic resonance (NMR), 13C-NMR, 31P-NMR, mass spectrometry (MS), thermogravimetry (TG), and conductivity measurements. The anticancer activities of the obtained compounds were measured by MTT. The preliminary results indicated that some compounds showed potent anticancer activities against HCT-8, Bel-7402, A549, and S180.

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.

Synthesis of 1-[ω-[(arylamino)carbonyl]alkyl]-4-(benzocycloalkyl)piperazines

A series of 1-[co-[(arylamino)carbonyl]alkyl]-4-(benzocycloalkyl)-piperazines (1a-v) was prepared either by reacting the precursor 4-[ω-[(arylamino)carbonyl]alkyl]piperazine (2a-j) with 1-chlorobenzocycloalkanes (3a-c) (Procedure A) or by reacting the N-aryl-ω-chloroalkanamides (5a-j) with the 4-(benzocycloalkyl)piperazines (10a-c) (Procedure B). The best yields were obtained using procedure A.

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.