Synthesis of 1-alkyl(aralkyl)-4-acyl-2-piperazinones (original) (raw)
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Synthesis and biological evaluation of piperazine derivatives as anthelmintic agents
The purpose of this study is based upon synthesis of a series of 1,4-disubstituted piperazine derivatives through two step reaction. This protocol involves the formation of various acid chlorides (3a-3j) through reaction of substituted acid with thionyl chloride in the presence of a drop of dimethyl formamide as a catalyst. The second step involves the reaction of compounds (3a-3j) with methyl piperazine, affording target compounds (5a-5j).The structures of target compounds were elucidated from the data of the different spectral methods of analysis. In addition, a mass spectrum, for a representative example, was carried out where the expected fragmentation pattern is in accordance with the structure of the proposed compound. The anthelmintic activity of the synthesized derivatives (5a-5j) was investigated in vitro against Eisenia fetida. All the investigational compounds (5a-5j) exhibited promising anthelmintic activity at minimal dose of 5mg/ml in comparison with reference drug Piperazine citrate.
Phenol-piperazine adducts showing anthelmintic properties
Journal of Medicinal Chemistry, 1973
the preparation of ethyl a~eto(l-adamantyl)actate.~ 0-Oxohex-anoate6 (35.9 g, 0.227 mol) and 1-adamant01 (34.5 g, 0.200 mol) were dissolved in 600 ml of pentane at 5". BF, was passed over the mixture for about 1 hr while maintaining the temperature at 5". Subsequently the reaction mixture was allowed to reach 15" and then it was cooled down to 5". After neutralization with KOH the solid was separated by filtration. The filtrate eventually gave an oil which was distilled at 20-40 pm: yield 15.4 g (22%); 92% pure by vpc. Guanidine hydrochloride (1.27 g, 13.3 mmol) was neutralized with a solution of sodium ethoxide (0.615 g, 26.8 mg-atom of Na in 100 ml of absolute EtOH). After cooling, 6 (3.89 g, 13.3 mmol) was added and the reaction mixture refluxed for 5 days. The work-up is the same as that previously described for 2-amino-4-hydroxy-5-(1-o~tyl)-6-rnethylpyrimidine.~ Recrystallization from absolute EtOHcharcoal and washing with Et,O gave 1.2 g (31%): uv max (absolute EtOH) 293,229 mp; uv min 253 mp; mp 298-299'. Anal. 2,4-Diamino-S-(l-adamantyl)-6-(1-propyl)pyrimidine Ethyl Sulfonate (4). The above compound 8 (1.7 g) was converted to its 4C1 derivative (mp 238-240") by POCI3-PCl5 as previously described for the preparation of 2-amino-4-chloro-5-(l-propyE6-methyl)
Int J Curr Pharm Res, 2011
Piperazines are the important group of compounds reported to have diverse biological activity like anthelmintic, antihistaminic, anticancer, antidepressant and hence the present study was undertaken in order to synthesize some piperazine derivatives and evaluate their biological properties. Experimental part involves the synthesis of Bis (β-chloroethyl) amine hydrochloride, then N-arylpiperazines hydrochloride which was then condensed with various alkyl bromides to form respective Arylpiperazine derivatives. The structures of the compounds were established on the basis of their IR and 1 HNMR spectral data. The compounds synthesized were studied for anti-bacterial activity using Ampicillin as standard drug respectively against four strains i.e. S. aureus, S. epidermidis, P. aeruginosa and E. coli. All the compounds show low to moderate activity while 1-(4chlorophenyl)-1-propyl piperazine shows excellent activity against S. aureus and 1-(4-methylphenyl)-1-propyl piperazine shows excellent activity against P. aeruginosa.
Synthesis and antimicrobial activity of N-alkyl and N-aryl piperazine derivatives
Bioorganic & Medicinal Chemistry, 2006
A series of substituted piperazine derivatives have been synthesized and tested for antimicrobial activity. The antibacterial activity was tested against Staphylococcus aureus (MTCCB 737), Pseudomonas aeruginosa (MTCCB 741), Streptomyces epidermidis (MTCCB 1824) and Escherichia coli (MTCCB 1652), and antifungal activity against Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger. All synthesized compounds showed significant activity against bacterial strains but were found to be less active against tested fungi. In vitro toxicity tests demonstrated that compounds 4d and 6a showed very less toxicity against human erythrocytes.N-Alkyl and N-aryl derivatives of piperazines have been synthesized and screened for antibacterial and antifungal activities. All the synthesized compounds show potent antibacterial activity and were found to be less active against fungi. Compounds 4d and 6a were found to be very less toxic to human erythrocytes when compared with gentamicin.
European Journal of Medicinal Chemistry, 2007
Cyano derivatives of N-alkyl and N-aryl piperazine have been synthesized and screened for antibacterial and antifungal activities. All the synthesized compounds showed the antibacterial activity against pathogenic strains of Staphylococcus aureus (MTCCB 737), Pseudomonas aeruginosa (MTCCB 741), Streptomyces epidermidis (MTCCB 1824) and Escherichia coli (MTCCB 1652) and antifungal activity against pathogenic strains of Aspergillus fumigatus (ITCC 4517), Aspergillus flavus (ITCC 5192) and Aspergillus niger (ITCC 5405). All compounds showed mild to moderate antimicrobial activity. However, compounds 3c, 4a and 6 showed potent antibacterial activity against pathogenic strains used in the study. Compounds 3a, 3b, 4b, and 4d showed mild to moderate antifungal activity against Aspergillus pathogenic strains. The compounds reported in this study were assessed for there cytotoxicity using MTT colorimetric assay on Hela cells. All the compounds showed cell viability more than the control drug gentamicin, with compound 2 having highest i.e. 95% cell viability.A series of cyano derivatives of N-alkyl and N-aryl piperazine were synthesized and evaluated for antibacterial and antifungal activity. Compound 3-(4-methyl-piperazin-1-yl)-propanitrile 4a showed potent antibacterial activity by broth dilution method with MIC at 19.5 μg/ml and 39.0 μg/ml against P. aeruginosa and E. coli, respectively, comparable to gentamicin as control drug. Compounds (4-benzyl-piperazin-1-yl)-acetonitrile 3c and 3-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-acetonitrile 6 showed a significant antibacterial activity with MIC at 19.5 μg/ml against S. aureus. In vitro cytotoxic studies of compound 3b exhibit 95% cell viability at the concentration used for antibacterial studies on Hela cells by using MTT colorimetric method.
Synthesis and in vitro antibacterial activity of N -alkyl and N -aryl piperazine derivatives
2011
A series of N-alkyl and N-aryl substituted piperazine derivatives have been synthesized in order to evaluate their antibacterial activity against four Gram-positive (Streptococcus mutans MTCC 890, Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121, Staphylococcus epidermidis MTCC 435) and one Gram-negative ( Escherichia coli MTCC 723) bacteria by disc diffusion and microbroth dilution methods. These compounds have been characterized by their MS, IR, 1 H and 13 C NMR spectral data. The benzyl piperazine derivatives 2-(4-benzylpiperazin-1-yl)-1-p-tolylethanone and 2-(4benzylpiperazin-1-yl)-1-(4-methoxyphenyl) ethanone show remarkable antibacterial activity even at low concentration against S. epidermidis , S. mutans and B. subtilis bacterial strains and are even close to the standard antibiotic, ampicillin. Furthermore, benzyl substitution increases antibacterial activity as compared to methyl and phenyl substituents under identical conditions.
Synthesis of 1-substituted-4-[4-(1H-indol-3-yl)butyl]piperazines
Arkivoc, 2013
A convenient synthetic route for preparation of various 4-[4-(1H-indol-3-yl)butyl]piperazines bearing heterocyclic and aliphatic substituents in position 1 has been developed. During this work some synthetic possibilities of common precursor, 4-[4-(1H-indol-3-yl)butyl]piperazine, were studied and evaluated.
Synthesis of 2,6-Bridged Piperazine-3-ones by N-Acyliminium Ion Chemistry
The Journal of Organic Chemistry, 2003
Several 2-substituted and 2,5-disubstituted piperazine-3,6-diones were synthesized starting from readily available R-amino acids. After activation of a lactam carbonyl via introduction of a methoxycarbonyl group onto nitrogen, this carbonyl was selectively reduced. Treatment of the resulting urethane with protic acid generated the corresponding N-acyliminium ion, which was trapped by a nucleophilic C2-side chain to provide 2,6-bridged piperazine-3-ones. Several aromatic, heteroaromatic, and nonaromatic side chains were used as π-nucleophiles. In addition, the effect of the presence of a C5-methyl group on the stereochemical outcome of the cyclization was examined.
Synthesis and Biological Evaluation of Some Piperazine Derivatives as Anti-Inflammatory Agents
Journal of Drug Delivery and Therapeutics, 2019
Some 1-((4-methylpiperazin-1yl)methyl)-1H-benzo[d]imidazole & 1-((4-phenylpiperazin-1yl)methyl)-1H-benzo[d]imidazole derivatives were synthesized through reaction of 1-substituted piperazines with different benzimidazole derivatives in methanol yielded the corresponding mannich bases (42-a to 42-i). All the synthesized compounds were elucidated by IR, 1H NMR and MASS spectroscopy. They were tested for anti-inflammatory activity using in-vivo (Carrageenan- induced rat paw edema model) method at a dose of 50mg/kg. result showed that compounds 42-c, 42-d and 42-h were found to be most potent in series. Keywords: 1,4-disubstituted Piperazine, Anti-inflammatory, Mannich Base.