136-72-1Relevant articles and documents
Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents
Ali, Yakub,Alam, Mohammad Sarwar,Hamid, Hinna,Husain, Asif,Bano, Sameena,Dhulap, Abhijeet,Kharbanda, Chetna,Nazreen, Syed,Haider, Saqlain
, p. 490 - 500 (2015)
Nineteen novel piperine based triazoles have been synthesized using click chemistry approach and were tested for in vivo anti-inflammatory activity. The most active compounds were evaluated for in vitro TNF-α expression. Compounds 3g and 3f were found to
The larvicidal activity of natural inspired piperine-based dienehydrazides against Culex pipiens
Tantawy, Ahmed H.,Farag, Shaimaa M.,Hegazy, Lamees,Jiang, Hong,Wang, Man-Qun
, (2020)
A series of piperine-based dienehydrazide derivatives were designed and synthesized to be used as insecticides against Culex pipiens. The chemical structure of compound 5n was confirmed by single-crystal x-ray diffraction. Their insecticidal activities of
Synthesis and antimicrobial evaluation of piperic acid amides and their lower homologues
Achanta, Prabhakar S.,Raj, Sneha,Horam, Soyar,Arockiaraj, Jesu,Bobbala, Ravi Kumar,Akkinepally, Raghuram Rao,Pasupuleti, Mukesh,Achanta, Appa Rao V. N.
, p. 366 - 373 (2020)
Seven piperic acid amides along with their lower homologs (12) were synthesized using HATU-DIPEA coupling reagent. All the synthesized derivatives were evaluated for their antibacterial activities against Staphylococcus aureus, Pseudomonas aeruginosa, and vancomycin-resistant P. aeruginosa. They were found to be more active on P. aeruginosa than on S. aureus. However, they did not exhibit potent activity on Vancomycin resistant P. aeruginosa. Among the tested compounds, methylenedioxycinnamic acid amide of anthranilic acid (MDCA-AA, 2a) was found to be most active against S. aureus with MIC of 3.125 μg/ml. The PAS and INH amides of piperic acid were screened against Mycobacterium tuberculosis H37Ra strain. They were found to be most active among all the tested compounds but were found to be less active than the standard drug, isoniazid.
Synthesis and insecticidal activity of new amide derivatives of piperine
De Paula, Vanderlucia F.,De A Barbosa, Luiz C.,Demuner, Antonio J.,Pilo-Veloso, Dorila,Picanco, Marcelo C.
, p. 168 - 174 (2000)
The natural lipophilic amides piperine and piperiline were isolated from Piper nigrum L (Piperaceae). Piperine was hydrolysed into piperic acid (85% yield) which was converted into 16 amides (28-89% yield). The contact toxicity of all synthetic amides, and also that of piperine and piperiline, at the dose 10 μg per insect, was evaluated for the Brazilian economically important insects Ascia monuste orseis Latr, Acanthoscelides obtectus Say, Brevicoryne brassicae L, Protopolybia exigua DeSaus and Cornitermes cumulans Kollar. The results demonstrated that the insects have different sensivities to the various amides, with mortality ranging from 0 to 97.5% according to the compound and insect species. (C) 2000 Society of Chemical Industry.
Synthesis, in vitro and in silico Anti-Proliferative Studies of Novel Piperiene-Oxadiazole and Thiadiazole Analogs
Amperayani,Parimi
, p. 2301 - 2307 (2019)
Piperine is a component of pepper which has earlier been reported as anticancer active compound. This work is emphasized on the design and synthesis of new hybrid piperine analogs by coupling piperine with the amine group of oxadiazoles and thiadiazoles.
Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi
Ribeiro, Tatiana Santana,Freire-De-Lima, Leonardo,Previato, Jose Osvaldo,Mendonca-Previato, Lucia,Heise, Norton,De Lima, Marco Edilson Freire
, p. 3555 - 3558 (2004)
We describe herein an evaluation of trypanocidal effects of the natural alkaloid piperine and twelve synthetic derivatives against epimastigote and amastigote forms of the protozoan parasite Trypanosoma cruzi, the causative agent of the incurable human disease, Chagas' disease. The results obtained point to piperine as a suitable template for the development of new drugs with trypanocidal activity.
Synthesis, Radical-Scavenging Activities, and Protective Effects against AAPH-Induced Oxidative Damage in DNA and Erythrocytes of Piperine Derivatives
Cao, Ruijun,Qin, Bei,Yang, Kuan
, (2020)
Piperine amino acid derivatives containing phenolic hydroxyl groups were synthesized using piperine as the raw material by amide hydrolysis, amidation, ester hydrolysis, and deacetalization. The obtained products were characterized by mass spectrometry and nuclear magnetic resonance. The antioxidant activity of the piperine derivatives was evaluated by the DPPH and ABTS scavenging rates and the total antioxidant capacity. The results showed that the piperine amino acid (4a-4d) had relatively weak radical-scavenging ability, while the piperine amino acid derivatives (5a-5d) containing phenolic hydroxyl groups had significant radical-scavenging effects. In addition, the total reducing ability of 5a-5d was better than that of piperine. The study also found that piperine derivatives containing phenolic hydroxyl groups played an important role in inhibiting oxidative damage in DNA and erythrocytes.
Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists
Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Ali, Yakub,Dhulap, Abhijeet,Alam, Perwez,Pasha, M. A. Qadar
, p. 354 - 362 (2016)
Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ-induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a-h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR-γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side-effects.
Natural inspired piperine-based ureas and amides as novel antitumor agents towards breast cancer
Elimam, Diaaeldin M.,Elgazar, Abdullah A.,El-Senduny, Fardous F.,El-Domany, Ramadan A.,Badria, Farid A,Eldehna, Wagdy M.
, p. 39 - 50 (2021/12/21)
In this work, the natural piperine moiety was utilised to develop two sets of piperine-based amides (5a–i) and ureas (8a–y) as potential anticancer agents. The anticancer action was assessed against triple negative breast cancer (TNBC) MDA-MB-231, ovarian A2780CP and hepatocellular HepG2 cancer cell lines. In particular, 8q stood out as the most potent anti-proliferative analogue against TNBC MDA-MB-231 cells with IC50 equals 18.7 μM, which is better than that of piperine (IC50 = 47.8 μM) and 5-FU (IC50 = 38.5 μM). Furthermore, 8q was investigated for its possible mechanism of action in MDA-MB-231 cells via Annexin V-FITC apoptosis assay and cell cycle analysis. Moreover, an in-silico analysis has proposed VEGFR-2 as a probable enzymatic target for piperine-based derivatives, and then has explored the binding interactions within VEGFR-2 active site (PDB:4ASD). Finally, an in vitro VEGFR-2 inhibition assay was performed to validate the in silico findings, where 8q showed good VEGFR-2 inhibitory activity with IC50 = 231 nM.
Natural inspired piperine-based sulfonamides and carboxylic acids as carbonic anhydrase inhibitors: Design, synthesis and biological evaluation
Elimam, Diaaeldin M.,Elgazar, Abdullah A.,Bonardi, Alessandro,Abdelfadil, Mohamed,Nocentini, Alessio,El-Domany, Ramadan A.,Abdel-Aziz, Hatem A.,Badria, Farid A.,Supuran, Claudiu T.,Eldehna, Wagdy M.
, (2021/09/06)
The natural product piperine, the major bioactive alkaloid present in black pepper fruits, has the ability to modulate the functional activity of several biological targets. In this study, we have utilized the natural piperine as a tail moiety to develop new SLC-0111 analogues (6a-d, 8 and 9) as potential carbonic anhydrase inhibitors. Thereafter, different functionalities, free carboxylic acid (11a-c), acetyl (13a) and ethyl ester (13b-c), were exploited as bioisosteres of the sulfamoyl functionality. All piperine-based derivatives were assessed for their inhibitory actions against four human (h) CA isoforms: hCA I, II, IX and XII. The best hCA inhibitory activity was observed for the synthesized primary piperine-sulfonamides (6a-d and 8). In particular, both para-regioisomers (6c and 8) emerged as the most potent hCA inhibitors in this study with two-digit nanomolar activity against hCA II (KIs = 93.4 and 88.6 nM, respectively), hCA IX (KIs = 38.7 and 68.2 nM, respectively), and hCA XII (KIs = 57.5 and 45.6 nM, respectively). Moreover, piperine-sulfonamide 6c was examined for its anti-cancer and pro-apoptotic actions towards breast MCF-7 cancer cell line. Collectively, piperine-based sulfonamides could be considered as a promising scaffold for development of efficient anticancer candidates with potent CA inhibitory activities.
Structure-based design, synthesis, and biological evaluation of novel piperine-resveratrol hybrids as antiproliferative agents targeting SIRT-2
Abdelazeem, Ahmed H.,Fouad, Ali,Jiang, Hong,Marzouk, Adel A.,Meng, Xiang-Gao,Tantawy, Ahmed H.,Wang, Man-Qun,Youssif, Bahaa G. M.
, p. 25738 - 25751 (2021/08/05)
A series of novel piperine-resveratrol hybrids5a-hwas designed, synthesized, and structurally elucidated by IR, and1H,13C, and19F NMR. Antiproliferative activities of5a-hwere evaluated by NCI against sixty cancer cell line
