Design, synthesis and antitubercular evaluation of novel series of N-[4-(piperazin-1-yl)phenyl]cinnamamide derivatives

Patel, Kavitkumar; Telvekar, Vikas N.

doi:10.1016/j.ejmech.2014.01.024

Cited by 29 publications

(18 citation statements)

References 18 publications

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“…In conclusion, novel diacyl (5a-5k) and alkyl-acyl (5l-5w) unsaturated piperazine compounds were synthesized by the acylation reactions of piperazine (1a), methacryloyl piperazine (1b), allyl piperazine (1c), and cinnamyl piperazine (1d) with suitable acyl chlorides and methacrylic anhydride in medium to high yields for the first time. All new compounds were characterized by 1 H NMR, 13 C NMR, HRMS, and FTIR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR and 13 C NMR spectra were recorded on Varian Mercury-400 High Performance Digital FT-NMR and cinnamylpiperazine, and metacrylic anhydride were purchased from Sigma Aldrich. Please note that the 1 H NMR spectra for known compounds and 1 H NMR, 13 C NMR, and HRMS spectra for all novel compounds can be found in the Supplementary information.…”

Section: Equipment and Used Chemicalsmentioning

confidence: 99%

“…Piperazine is also a useful linker for bioactive structures. Many biological activity studies were performed on piperazine-containing structures, such as anticonvulsant [11], antibacterial [12], antituberculosis [13], antiviral [14], anticancer [15], antimalarial [16], and acetylcholine esterase inhibition [17].…”

Section: Introductionmentioning

confidence: 99%

“…In this study, based on these properties of piperazines, we obtained various unsaturated diacyl and alkyl-acyl cinnamyl, ally, and acrylamide piperazines bearing unsaturated moieties, which are potential bioactive compounds and starting reagents for synthesizing many other potential bioactive molecules. All new synthesized compounds were characterized by 1 H NMR, 13 C NMR, HRMS, and FTIR spectroscopy. Other compounds that are available in the literature were characterized by 1 H NMR spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of unsaturated diacyl and alkyl-acyl piperazinederivatives

Sarı¹,

Ünalan²,

Yılmaz³

2019

Turk J Chem

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The aim of this study is to obtain new unsaturated piperazine compounds by the reactions of piperazine (1a) and piperazine derivatives (1b-1d) with acylation reactive groups (2a-2j). Methacryloyl piperazine (1b) was synthesized from the reaction of methacrylic anhydride with piperazine (1a). Acyl chlorides (2b-2d) were prepared from the reaction of thionyl chloride with carboxylic acids (3a-3c) obtained as a result of the reaction with malonic acid and suitable aldehyde (5-methylfuran-2-carbaldehyde for 3a, cinnamaldehyde for 3b, and thiophene-2-carbaldehyde for 3c), respectively, by literature methods. Acyl chlorides 2e and 2f were obtained from the reaction of commercially purchased carboxylic acids 3d and 3e with thionyl chloride. Acyl chlorides (2g-2j) were synthesized from the reaction of thionyl chloride with carboxylic acids (3d-3g) transformed from hydrolyzation of esters (4a-4d) obtained as a result of the reaction of triethyl phosphonoacetate with a suitable ketone (acetophenone for 4a, benzophenone for 4b, 1-(5-methylfuran-2-yl)ethan-1-one for 4c, and 1-(thiophen-2-yl)ethan-1-one for 4d), respectively, by literature methods. Unsaturated piperazine derivatives 5a and 5b were obtained from the reaction of 1b with 2b and 2e, respectively. In addition, from the reaction of 1b and acyl chlorides (2b-2j), unsaturated piperazines (5c-5k) were synthesized in medium to good yields (63%-84%). Also, 5l-5g and 5r-5w were obtained from the reaction of allyl piperazine (2c) and cinnamyl piperazine (2d) with acyl chlorides (2a-2f).

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Section: Resultsmentioning

confidence: 99%

Section: Equipment and Used Chemicalsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and characterization of unsaturated diacyl and alkyl-acyl piperazinederivatives

Sarı¹,

Ünalan²,

Yılmaz³

2019

Turk J Chem

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“…These compounds were screened for in vitro antimycobacterial activity against H37Rv strain. Of the developed compounds, compound 171 was found to be most active with MIC of 3.125 µg/ml[275]. Various piperazine substituted phenanthridine analogues were synthesized and evaluated for antitubercular activity by Nagesh et al Compounds 172a, 172b and 172c elicited excellent activities against H37Rv strain with MIC of 1.56 µg/mL[276].…”

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confidence: 99%

Piperazine scaffold: A remarkable tool in generation of diverse pharmacological agents

Shaquiquzzaman

Verma

Marella

et al. 2015

European Journal of Medicinal Chemistry

198

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Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Wang

et al. 2020

Drug Development Research

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Tuberculosis (TB), a chronic infectious disease, is one of the greatest risks to human beings and 10 million people were diagnosed with TB and 1.6 million died from this disease in 2017. In addition, with the emergence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB), the TB situation has become even worse, which has aggravated the mortality and spread of this disease.To overcome this problem, research into novel antituberculosis agents with enhanced activities against MDR-TB, reduced toxicity, and shortened duration of therapy is of great importance. Fortunately, many novel potential anti-TB drug candidates with five-membered rings, which are most likely to be effective against sensitive and resistant strains, have recently entered clinical trials. Different five-membered rings such as furans, pyranoses, thiazoles, pyrazolines, imidazoles, oxazolidinone, thiazolidins, isoxazoles, triazoles, oxadiazoles, thiadiazoles, and tetrazoles have been designed, prepared, and evaluated for their antimycobacterial activity against Mycobacterium tuberculosis. In this article, we highlight the recent advances made in the discovery of novel five-membered ring compounds and focus on their antitubercular activities, toxicity, structure-activity relationships, and mechanisms of action. K E Y W O R D Santi-TB drug, antitubercular activities, five-membered ring, MDR-TB, tuberculosis

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Design, synthesis and antitubercular evaluation of novel series of N-[4-(piperazin-1-yl)phenyl]cinnamamide derivatives

Cited by 29 publications

References 18 publications

Synthesis and characterization of unsaturated diacyl and alkyl-acyl piperazinederivatives

Synthesis and characterization of unsaturated diacyl and alkyl-acyl piperazinederivatives

Piperazine scaffold: A remarkable tool in generation of diverse pharmacological agents

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

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