Synthesis and antimicrobial activity of N-alkyl and N-aryl piperazine derivatives

Chaudhary, Preeti; Kumar, Rupesh; Verma, Akhilesh K.; Singh, Devender; Yadav, Vipul; Chhillar, Anil Kumar; Sharma, Gainda L.; Chandra, Ramesh

doi:10.1016/j.bmc.2005.10.032

Cited by 167 publications

(69 citation statements)

References 39 publications

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“…Substituted piperazines are important pharmacophores that can be found in many marketed drugs, such as the Merck HIV protease inhibitor Crixivan. 16 This motif is also displaying antimicrobial, 17 anticancer, 18 antidepressant and antioxidant activity. 19 In recent years, alkyl chain arylpiperazine derivatives represent one of the important classes of building template in medicinal chemistry.…”

Section: Figure 1 Some Of the Important Bioactive Tetrazole Compoundsmentioning

confidence: 99%

Regioselective synthesis and preliminary cytotoxic activity properties of tetrazole appendage N-substituted piperazine derivatives

Dileep¹,

Katiki²,

Rao³

et al. 2017

Org. Commun.

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A series of 1-(4-substituted)-4-(3-((1-(substituted)-1H-tetrazol-5-yl)thio)propyl)piperazine derivatives were (6a-t) synthesized by KF-Al 2 O 3 mediated S-alkylation of 5-thio-substituted tetrazole with 1-(3-chloropropyl)-4-(4-substituted)piperazine. The structures of the newly synthesized compounds were characterized by NMR and MS spectral data. Further, the regioselective formation of C-S bond was unambiguously confirmed by single crystal Xray diffraction. All the synthesized compounds were screened for their in vitro cytotoxic activities against two cancer cell lines: DU-145 (prostate cancer) and HeLa (cervical cancer). These cell lines were utilized in MTT assays and the obtained results were compared to doxorubicin, and their IC 50 values were determined. Among the compounds tested, 6f, 6j, 6m, 6n, 6o, 6q, 6r and 6t showed considerable potent activity, while the compound 6p exhibited significant potent activity against DU-145 and HeLa cancer cell lines compare to standard Doxorubicin.

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Section: Figure 1 Some Of the Important Bioactive Tetrazole Compoundsmentioning

confidence: 99%

Regioselective synthesis and preliminary cytotoxic activity properties of tetrazole appendage N-substituted piperazine derivatives

Dileep¹,

Katiki²,

Rao³

et al. 2017

Org. Commun.

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“…Piperazine derivatives are known to possess the properties of triple reuptake inhibitors [1], norovirus inhibitors [2], cannabinoid CB1 receptor agonists [3], antagonists for the melanocortin-4 receptor [4], antimicrobials [5], enzyme inhibitors [6], etc. This moiety has also found applications in the field of engineering [7] and polymers [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-[4-(2-furoyl)-1-piperazinyl]-N- (substituted)propanamides as promising antibacterial agents with mild cytotoxicity

et al. 2018

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Purpose: To evaluate the antibacterial activity and cytotoxicity of a series of molecules with amalgamation of furoyl, piperazine and amide moieties. Methods: New derivatives, namely 3-[4-(2-furoyl)-1-piperazinyl]-N-(substituted)propanamides, were synthesized and evaluated for their antibacterial activity and toxicity to mammalian cells. The synthesis was initiated by treating different aryl/aralkyl amines (1a-u) with 3-bromopropionyl chloride (2) to obtain the solid electrophiles 3a-u, which were collected by filtration. Thereafter, and 2-furoyl-1-piperazine (4) at equimolar ratios were allowed to react in acetonitrile and in the presence of a base, K2CO3, to form the target compounds, 5a-u. Structural elucidation was carried out using EI-MS (electron impact mass spectrometry), IR (infrared) and 1H-NMR (proton nuclear magnetic resonance). The antibacterial activity of the synthesized compounds was evaluated against various bacterial strains. Furthermore, hemolysis was determined to assess cytotoxicity using bovine red blood cells. Results: Molecules 5g, 5a, 5p, 5g and 5i were found to be potent agents against S. aureus, S. typhi, P. 8.34 ± 0.55, 8.37 ± 0.12, 8.65 ± 0.57, 8.97 ± 0.12 and 9.24 ± 0.50 µM, compared to 7.80 ± 0.19, 7.45 ± 0.58, 7.14 ± 0.58, 7.16 ± 0.58 and 7.29 ± 0.90 aeruginosa, E. coli and B. subtilis with respective minimum inhibitory concentration (MIC) values of

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“…Various methods are reported for the synthesis of piperizine derivatives, though many piperazine derivatives occur naturally, piperazine can be synthesized by reacting alcoholic ammonia with 1,2-dichloroethane, by the action of sodium and ethylene glycol on ethylene diamine hydrochloride, or by reduction of pyrazine with sodium in ethanol 7 various research has been cariied out on synthesis on piperizine and pirazine and those respective deivatives were found to be useful in combating various diesase some important derivatives of piperazines which were already proved to be pharmacologically and biologically are I,e 5-methylpyrazine-2-Carbohydrazide possess antibacterial 9 and antiinflamatory activity 10 N-aryl and N-alkyl piperazine derivatives 11,12 posses antibacterial activity and enhanced antibacterial activity is achieved by incorporation of triazine ring in the piperizine ring 13 Mannich bases derived from n-methyl piperazine is found to active against cancer 14 .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and antimicrobial activity of N-alkyl and N-aryl piperazine derivatives

Cited by 167 publications

References 39 publications

Regioselective synthesis and preliminary cytotoxic activity properties of tetrazole appendage N-substituted piperazine derivatives

Regioselective synthesis and preliminary cytotoxic activity properties of tetrazole appendage N-substituted piperazine derivatives

Synthesis of 3-[4-(2-furoyl)-1-piperazinyl]-N- (substituted)propanamides as promising antibacterial agents with mild cytotoxicity

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