- Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents
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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
- Ali, Yakub,Alam, Mohammad Sarwar,Hamid, Hinna,Husain, Asif,Bano, Sameena,Dhulap, Abhijeet,Kharbanda, Chetna,Nazreen, Syed,Haider, Saqlain
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- Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus
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A total of eighteen piperic acid (PA) and 4-ethylpiperic acid (EPA) amides (C1–C18) with α-, β- and γ-amino acids were synthesized, characterized and evaluated for their efflux pump inhibitory activity against ciprofloxacin resistant Staphylococcus aureus. The amides were screened against NorA overexpressing S. aureus SA-1199B and wild type S. aureus SA-1199 using ethidium bromide as NorA efflux pump substrate. EPI C6 was found to be most potent and reduced the MIC of ciprofloxacin by 16 fold followed by C18 which showed 4 fold reduction of MIC. Ethidium bromide efflux inhibition and accumulation assay proved these compounds as NorA inhibitors.
- Wani, Naiem Ahmad,Singh, Samsher,Farooq, Saleem,Shankar, Sudha,Koul, Surrinder,Khan, Inshad Ali,Rai, Rajkishor
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- The larvicidal activity of natural inspired piperine-based dienehydrazides against Culex pipiens
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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
- Tantawy, Ahmed H.,Farag, Shaimaa M.,Hegazy, Lamees,Jiang, Hong,Wang, Man-Qun
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- Synthetic piperine amide analogs with antimycobacterial activity
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Piperine amide analogs are synthesized by replacement of the piperidine moiety with different types of cyclic amines, including adamantyl and monoterpene-derived fragments. The compounds are screened for activity against Mycobacterium tuberculosis H37Rv. The most potent compounds are the 1-adamantyl and the monoterpene-derived hybrids, which combine nanomolar antimycobacterial activity with low cytotoxicity against human cells. The presence of quaternary carbon atom as main structural requirement for anti-TB activity is pointed out by a QSAR study. The most promising compound is the (+)-isopinocampheylamine-derived amide which is characterized with selectivity index of 1387.8.
- Philipova, Irena,Valcheva, Violeta,Mihaylova, Rositsa,Mateeva, Mina,Doytchinova, Irini,Stavrakov, Georgi
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- Synthesis and antimicrobial evaluation of piperic acid amides and their lower homologues
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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.
- Achanta, Prabhakar S.,Raj, Sneha,Horam, Soyar,Arockiaraj, Jesu,Bobbala, Ravi Kumar,Akkinepally, Raghuram Rao,Pasupuleti, Mukesh,Achanta, Appa Rao V. N.
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- AMIDES OF OTTONIA CORCOVADENSIS
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Key Word Index-Ottonia corcovadensis; Piperaceae; amides; piperovatine; piperlonguminine; isopiperlonguminine; corcovadine; isocorcovadine; 1H NMR and mass spectrometry.Abstract-Five amides were isolated from the roots of Ottonia corcovadensis.Two are the known piperlonguminine and piperovatine.The other three are new and their structures are: (2Z,4Z)-N-isobutyl-5-(3,4-methylenedioxyphenyl)-penta-2,4-dienoic amide for isopiperlonguminine; (2E,4E)-N-(2-methyl-2-acetoxypropyl)-5-(3,4-methylenedioxyphenyl)-penta-2,4-dienoic amide for corcovadine; and (2Z,4Z)-N-(2-methyl-2-acetoxypropyl)-5-(3,4-methylenedioxyphenyl)-penta-2,4-dienoic amide for isocorcovadine.
- Costa, Sonia Soares,Mors, Walter B.
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- Synthesis and insecticidal activity of new amide derivatives of piperine
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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.
- De Paula, Vanderlucia F.,De A Barbosa, Luiz C.,Demuner, Antonio J.,Pilo-Veloso, Dorila,Picanco, Marcelo C.
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- Synthesis, in vitro and in silico anti-bacterial analysis of piperine and piperic ester analogues
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A set of 12 analogues of piperine was designed, replacing the amide functional group of the molecule with different aliphatic and aromatic ester functional groups. Molecular docking studies of these molecules with FDA-approved target proteins for anti-bacterial drugs were done. The binding energy of the proteins and the ligands were low and the analogues were found to be drug-like based on the ADME results; hence, the molecules were synthesized. The synthesized compounds were tested for their anti-bacterial property against six bacterial species via Agar well-diffusion method. Acinetobacter baumannii, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Enterococcus faecalis and Staphylococcus epidermidis were the strains tested. The overall susceptibility is higher in gram-positive. The analogues showed better activity than piperine. The analogues, propyl piperic ester (P3) and 2-fluorophenyl piperic ester (P9) and 4-fluorophenyl piperic ester (P10) showed comparatively bigger inhibition zones for all the strains.
- Sivashanmugam, Arthi,Velmathi, Sivan
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- Synthesis, in vitro and in silico Anti-Proliferative Studies of Novel Piperiene-Oxadiazole and Thiadiazole Analogs
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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.
- Amperayani,Parimi
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- A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues
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A quantitative synthesis of piperine from commercially available starting material is presented. The synthesis relies on a stereoselective nucleophilic attack of an in situ generated cuprate onto a cyclobutene lactone. The so-formed aryl-substituted cyclobutene spontaneously undergoes a conrotatory 4π-electrocyclic ring opening to form the 4-aryl pentadienoic acid as a single diastereoisomer. The high-yielding synthesis can be easily modulated on the aryl and on the amide moiety for the synthesis of a wide range of piperine analogues.
- Bauer, Adriano,Nam, Jun-Hyun,Maulide, Nuno
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- Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi
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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.
- Ribeiro, Tatiana Santana,Freire-De-Lima, Leonardo,Previato, Jose Osvaldo,Mendonca-Previato, Lucia,Heise, Norton,De Lima, Marco Edilson Freire
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- Synthesis and biological activity of piperine derivatives as potential PPARγ agonists
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Introduction: Peroxisome proliferator-activated receptor γ (PPARγ) plays a key role in glucose, which is a ligand-mediated transcription factor. The lipid homeostasis often serves as a pharmacological target for new drug discovery and development. Materials and Methods: In the research, we synthesized a series of piperine derivatives and then used a fluorescence polarization-based PPARγ ligand screening assay to evaluate the agonistic activity of PPARγ. Then, we cultured human normal hepatocytes, which were treated with 100μM compounds 2a, 2t or 3d. Then, the levels of PPARγ gene were determined so as to show whether the compounds could activate or inhibit the expression of PPARγ. Results: A total of 30 piperine derivatives were synthesized and evaluated. Compound 2a was identified as a potential PPARγ agonist with IC50 at 2.43 μM, which is 2 times more potent than the positive control rosiglitazone with IC50 at 5.61μM. The human hepatocytes cells were cultured and treated with compounds 2a, 2t or 3d as described in the “Materials and Methods” section. We found that compounds 2a, 2t and 3d could activate PPARγ by 11.8, 1.9 and 7.0 times compared with the “blank”, with compound 2a activation being the most significant. Molecular docking studies indicated that the piperine derivative 2a stably interacts with the amino acid residues of the PPARγ complex active site, which is consistent with the results of the in vitro PPARγ ligand screening assay.
- Cui, Jian,Lee, David Yue-Wei,Liu, Jing,Liu, Tonghua,Wang, Yanli,Wu, Lili,Yao, Yuan
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- Synthesis, Radical-Scavenging Activities, and Protective Effects against AAPH-Induced Oxidative Damage in DNA and Erythrocytes of Piperine Derivatives
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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.
- Cao, Ruijun,Qin, Bei,Yang, Kuan
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- Synthesis and in vitro and in silico antimicrobial studies of novel piperine–pyridine analogs
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Pepper is used as a food additive and preservatives because of its antimicrobial activity. Piperine, an alkaloid amide derived from pepper, is the cause of its biological activity. Aminopyridine is a well-known antimicrobial agent. In?silico studies proved that conjugation of piperine with substituted aminopyridine results in a new hybrid molecule with improved antimicrobial activity compared with the parent molecules. The present work describes design and synthesis of novel piperine analogs with substituted aminopyridine analogs (PY1–8). The synthesized compounds were characterized by 1H and 13C nuclear magnetic resonance (NMR), infrared (IR), and mass spectroscopy and subjected to antimicrobial testing using bacterial strains Bacillus subtilis, Streptobacillus, Staphylococcus aureus, Escherichia coli, and Salmonella typhi and fungal strains Aspergillus niger, A.?flavus, and A.?fumigatus.
- Amperayani, Karteek Rao,Kumar, Kottakki Naveen,Parimi, Uma Devi
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- Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists
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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.
- Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Ali, Yakub,Dhulap, Abhijeet,Alam, Perwez,Pasha, M. A. Qadar
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- Th1-biased immunomodulation and in vivo antitumor effect of a novel piperine analogue
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Natural products have an important role as prototypes in the synthesis of new anticancer drugs. Piperine is an alkaloid amide with antitumor activity and significant toxicity. Then, the N-(p-nitrophenyl)acetamide piperinoate (HE-02) was synthesized, and t
- Athayde-Filho, Petr?nio,Barbosa-Filho, José Maria,Batista, Tatianne,Brito, Monalisa,Costa, Normando,Cruz, Ryldene,Ferreira, Rafael,Leite, Fagner,Lira, Bruno,Magalh?es, Hemerson,Mangueira, Vivianne,Moura, Ana Paula,Santos, Jephesson,Sobral, Marianna,Sousa, Tatyanna,Souza, Helivaldo,Veras, Robson,Vieira, Giciane
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- Natural inspired piperine-based ureas and amides as novel antitumor agents towards breast cancer
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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.
- Elimam, Diaaeldin M.,Elgazar, Abdullah A.,El-Senduny, Fardous F.,El-Domany, Ramadan A.,Badria, Farid A,Eldehna, Wagdy M.
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- The development of novel cytochrome P450 2J2 (CYP2J2) inhibitor and the underlying interaction between inhibitor and CYP2J2
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Human Cytochrome P450 2J2 (CYP2J2) as an important metabolic enzyme, plays a crucial role in metabolism of polyunsaturated fatty acids (PUFAs). Elevated levels of CYP2J2 have been associated with various types of cancer, and therefore it serves as a potential drug target. Herein, using a high-throughput screening approach based on enzymic activity of CYP2J2, we rapidly and effectively identified a novel natural inhibitor (Piperine, 9a) with IC50 value of 0.44 μM from 108 common herbal medicines. Next, a series of its derivatives were designed and synthesised based on the underlying interactions of Piperine with CYP2J2. As expected, the much stronger inhibitors 9k and 9l were developed and their inhibition activities increased about 10 folds than Piperine with the IC50 values of 40 and 50 nM, respectively. Additionally, the inhibition kinetics illustrated the competitive inhibition types of 9k and 9l towards CYP2J2, and K i were calculated to be 0.11 and 0.074 μM, respectively. Furthermore, the detailed interaction mechanism towards CYP2J2 was explicated by docking and molecular dynamics, and our results revealed the residue Thr114 and Thr 315 of CYP2J2 were the critical sites of action, moreover the spatial distance between the carbon atom of ligand methylene and Fe atom of iron porphyrin coenzyme was the vital interaction factor towards human CYP2J2.
- Tian, Xiangge,Zhou, Meirong,Ning, Jing,Deng, Xiaopeng,Feng, Lei,Huang, Huilian,Yao, Dahong,Ma, Xiaochi
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p. 737 - 748
(2021/03/16)
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- Natural inspired piperine-based sulfonamides and carboxylic acids as carbonic anhydrase inhibitors: Design, synthesis and biological evaluation
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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.
- 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.
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- NOVEL COMPOUND FOR PREVENTING OR TREATING NEUROINFLAMMATORY DISEASE AND PHARMACEUTICAL COMPOSITION INCLUDING THE SAME
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The present invention relates to a novel 2 -halogen or haloalkyl 4,5 -dihydroxy pyrronin analogue and a composition for preventing or treating neuroinflammatory diseases comprising the same as an active ingredient. A composition comprising LPS -stimulated
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Paragraph 0090; 0091
(2021/06/01)
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- Structure-based design, synthesis, and biological evaluation of novel piperine-resveratrol hybrids as antiproliferative agents targeting SIRT-2
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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
- Abdelazeem, Ahmed H.,Fouad, Ali,Jiang, Hong,Marzouk, Adel A.,Meng, Xiang-Gao,Tantawy, Ahmed H.,Wang, Man-Qun,Youssif, Bahaa G. M.
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p. 25738 - 25751
(2021/08/05)
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- Disruption of redox homeostasis with synchronized activation of apoptosis highlights the antifilarial efficacy of novel piperine derivatives: An in vitro mechanistic approach
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A series of novel piperine derivatives were synthesized with high yield and were evaluated for its antifilarial potential against the bovine filarial parasite Setaria cervi. Among 21 (3a-3u) compounds screened, three of them (3k, 3l, 3s) showed significan
- Joardar, Nikhilesh,Shit, Pradip,Halder, Satyajit,Debnath, Utsab,Saha, Sudipto,Misra, Anup Kumar,Jana, Kuladip,Sinha Babu, Santi P.
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p. 343 - 360
(2021/05/05)
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- A novel piperine analogue exerts in vivo antitumor effect by inducing oxidative, antiangiogenic and immunomodulatory actions
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Structural diversity characterizes natural products as prototypes for design of lead compounds. The aim of this study was to synthetize, and to evaluate the toxicity and antitumor action of a new piperine analogue, the butyl 4-(4-nitrobenzoate)-piperinoat
- Abrantes, Renata Albuquerque de,Athayde-Filho, Petr?nio Filgueiras de,Batista, Tatianne Mota,Brand?o, Maria Cláudia Rodrigues,Cavalcanti, Raquel Fragoso Pereira,Duarte, Samia Sousa,Farias, Davi Felipe,Ferreira, Rafael Carlos,Leite, Fagner Carvalho,Lisboa, Thaís Mangeon Honorato,Mangueira, Vivianne Mendes,Medeiros, Karina Carla de Paula,Silva, Daiana Karla Frade,Sobral, Marianna Vieira,Sousa, Tatyanna Kélvia Gomes de,Trindade, Emmely Oliveira da
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- New Diesters Derived from Piperine: In silico Study and Evaluation of Their Antimicrobial Potential
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Piperine, previously extracted from black pepper (Piper nigrum L.), was used as a precursor for the synthesis of twelve new diester derivatives. The final products were obtained through the bimolecular nucleophilic substitution reaction (SN2) of the alkyl 2-chloroacetates and the salt of piperic acid, obtained from the basic hydrolysis of piperine. The compounds were synthesized with yields of 55-84% and characterized by infrared spectroscopy and 1H and 13C nuclear magnetic resonance. The evaluation of the compounds’ potential as new drug candidates was done through an in silico study of ADME properties (absorption, distribution, metabolization and excretion) and evaluation of antimicrobial activity against bacterial strains (Staphylococcus aureus and Pseudomonas aeruginosa), yeasts (Candida albicans and Candida tropicalis) and filamentous fungi (Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger). The in silico study showed that the compounds were good drug candidates and antimicrobial evaluation demonstrated that 9 of the 12 compounds exhibited a minimum inhibitory concentration (MIC) ranging 1024-256 μg mL?1
- Barbosa-Filho, José M.,Brand?o, Maria Cláudia R.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes D.,Souza, Helivaldo D. S.,Trindade, Emmely O.,de Athayde-Filho, Petr?nio F.
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p. 1668 - 1678
(2020/10/09)
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- Synthesis, in silico study and antimicrobial activity of new piperine derivatives containing substituted δ-esters
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A series of fifteen new piperine-derived diesters was synthesized through the substitution reaction between the salt of piperic acid, obtained through piperine basic hydrolysis, with the δ-chloro-esters, obtained through the cleavage of tetrahydrofuran (THF) with acyl chlorides in the presence of ZnCl2. The final compounds were obtained with yields ranging from 50 to 84% and were characterized by infrared (IR) and 1H and 13C nuclear magnetic resonance spectroscopy (NMR). The new compounds were evaluated in silico in regard to their ADME (absorption, distribution, metabolism, and excretion) properties, and in vitro for their antimicrobial activity against bacteria strains (Staphylococcus aureus and Pseudomonas aeruginosas), yeast fungi (Candida albicans and C. tropicalis) and filamentous fungi (Aspergillus fumigatus, A. flavus and A. niger). The results from the in silico studies of Lipinski's rule of five showed that most compounds present good pharmacological possibilities, and the results from in vitro antimicrobial activity showed that 8 of the 15 synthesized compounds displayed antimicrobial activity, inhibiting the growth of 40-80% of tested strains, with a minimum inhibitory concentration (MIC) interval ranging from 1024 to 256 μg mL-1
- Barbosa-Filho, José M.,Brandao, Maria C. R.,De Athayde-Filho, Petr?nio F.,Dutra, Thalisson F.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes Diniz,Trindade, Emmely O.
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p. 2590 - 2602
(2020/11/18)
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- Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl
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Piperine was used in this study in its raw form, and different steps, such as amide hydrolysis and amidation, were used to synthesize piperine derivatives containing a phenolic hydroxyl group. DPPH and ABTS free radical scavenging assays were used to asse
- Cao, Ruijun,Qin, Bei,Yang, Kuan
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- Metabolization of Insecticidal Amides from Leaves of Piper tuberculatum by Heraclydes hectorides and Naupactus bipes
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Amides have been recognized as potent insecticidal natural products but, despite their variety of targets and mechanisms of action, their metabolic fate in insects is virtually unknown. The currently accepted hypothesis is that specialist herbivores are capable of biotransforming xenobiotics rendering them more polar and excretable while generalist insects do not have comparable capacity. The leaves from Piper tuberculatum, rich in insecticide amides, were offered to two insect species found on Piper leaves under natural conditions and also to four generalist grasshoppers in order to compare their capacity of biotransforming xenobiotics. The amides 1-7 were identified in the P. tuberculatum leaves and their corresponding carboxylic acids 8-13 were detected in frass samples of two host insects suggesting that these species promote the amides hydrolysis. The four generalist grasshoppers when offered P. tuberculatum leaves, starved to death after 72 h, indicating a strong antifeedant activity of P. tuberculatum leaves.
- Ramos, Clécio S.,Silva, Marcílio W.F.,Moraes, Marcilio M.,Almeida, Argus V.,Vanin, Sérgio A.,Kato, Massuo J.
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p. 724 - 730
(2020/04/27)
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- A nonpeptidyl molecule modulates apoptosis-like cell death by inhibiting P. Falciparum metacaspase-2
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Metacaspases are novel cysteine proteases found in apicomplexan whose function is poorly understood. Our earlier studies on Plasmodium falciparum metacaspase-2 (PfMCA-2) revealed that the caspase inhibitor, Z-FA-FMK efficiently inhibited PfMCA-2 activity and, expression, and significantly blocked in vitro progression of the parasite developmental cycle via apoptosis-like parasite death. Building on these findings, we synthesized a set of novel inhibitors based on structural modification of Z-FA-FMK with the amides of piperic acid and investigated their effect on PfMCA-2. One of these analogs, SS-5, specifically inhibited the activity and expression of PfMCA-2. The activities of some other known malarial proteases (falcipains, plasmepsins and vivapain), and human cathepsins-B, D and L, and caspase-3 and -7 were not inhibited by SS-5. SS-5 blocked the development of P. falciparum in vitro (IC50 1 μM) and caused prominent morphological distortions. Incubation with SS-5 led to persistent parasite oxidative stress accompanied by depolarization of mitochondrial potential and accumulation of intracellular Ca2+. SS-5 also inhibited the development of P. berghei in a murine model. Our results suggest that the inhibition of PfMCA-2 results in oxidative stress, leading to apoptosis-like parasite death. Thus, SS-5 offers a starting point for the optimization of new antimalarials, and PfMCA-2 could be a novel target for antimalarial drug discovery.
- Kalia, Inderjeet,Kashif, Mohammad,Pandey, Kailash C.,Prasad, Kona Madhavinadha,Rai, Rajkishor,Shankar, Sudha,Singh, Agam P.,Vandana
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p. 1323 - 1344
(2020/06/04)
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- Development of piperic acid-based monoamine oxidase inhibitors: Synthesis, structural characterization and biological evaluation
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A series of piperic acid esters and amides were synthesized using a two-step strategy. Mass spectrometry and unidimensional (1H NMR, 13C NMR, DEPT) and bidimensional (COSY, HSQC, HMBC) NMR methodologies were used to study the molecular structure of the final compounds, resulting in the assignment of all detected signals. Preliminary biological data of piperine and the derivatives thereof showed that piperic acid 2 and amides 3 and 4 did not display significant inhibitory activity at 10 μM against both hMAO-A and hMAO-B. In contrast, the esters 5 and 6 displayed relevant hMAO inhibitory activities, with IC50 values for hMAO-B lower than piperine and within the nanomolar range (compound 1: IC50 = 1.05 μM; compound 6: IC50 = 169 nM; compound 5: IC50 = 156 nM). Moreover, X-ray crystallographic analyses showed relevant differences between amides 3 and 4 and esters 5 and 6 constituting a valuable information to understand the ligand-target interactions. Additional studies are warranted for a systematic lead optimization process that can lead in the future to a more potent and selective hMAO-B inhibitor based on piperine scaffold.
- Chavarria, Daniel,Cagide, Fernando,Pinto, Miguel,Gomes, Lígia R.,Low, John N.,Borges, Fernanda
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p. 298 - 307
(2019/02/07)
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- Synthesis and antimicrobial activity of piperine analogues containing 1,2,4-triazole ring
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A series 1,2,4-triazole piperine analogues (TP1-TP6) were designed and synthesized. The structures were confirmed using 1H NMR and 13C NMR. Antibacterial study was done using Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative microorganisms (E. coli and Pseudomonas aeruginosa) by disc diffusion method. Compound containing chloro substitution (TP6) showed the highest effect, while compound TP1, TP3, TP4, TP5 showed the moderate activity.
- Kumar, Kottakki Naveen,Amperayani, Karteek Rao,Ummdi, V. Ravi Sankar,Parimi, Uma Devi
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p. 1077 - 1080
(2019/04/05)
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- PROCESS FOR THE PREPARATION OF PIPERINE
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The present application relates to a process for the preparation of piperine of high purity having low concentrations of isomeric impurities.
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(2019/05/02)
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- Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies
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Piperine has been associated with neuroprotective effects and monoamine oxidase (MAO) inhibition, thus being an attractive scaffold to develop new antiparkinsonian agents. Accordingly, we prepared a small library of piperine derivatives and screened the inhibitory activities towards human MAO isoforms (hMAO-A and hMAO-B). Structure-activity relationship (SAR) studies pointed out that the combination of α-cyano and benzyl ester groups increased both potency and selectivity towards hMAO-B. Kinetic experiments with compounds 7, 10 and 15 indicated a competitive hMAO-B inhibition mechanism. Compounds 15 and 16, at 10 μM, caused a small but significant decrease in P-gp efflux activity in Caco-2 cells. Compound 15 stands out as the most potent piperine-based hMAO-B inhibitor (IC50 = 47.4 nM), displaying favourable drug-like properties and a broad safety window. Compound 15 is thus a suitable candidate for lead optimization and the development of multitarget-directed ligands.
- Borges, Fernanda,Chavarria, Daniel,Fernandes, Carlos,Gil-Martins, Eva,Oliveira, Paulo J.,Remi?o, Fernando,Silva, Catia,Silva, Renata,Silva, Tiago,Silva, Vera,Soares, Pedro
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- Piperine synthesis method
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The invention discloses a piperine synthesis method. According to the synthesis method, 5-(1,2-methylenedioxyphenyl)-2-pentenal is taken as the primary raw material; a palladium catalyst is used, oxygen is taken as the oxidizing agent, trifluoroacetic acid is taken as the additive, in a polar organic solvent, one-step oxidation-dehydrogenation is performed to obtain 5-(1,2-methylenedioxyphenyl)-2,4-dipentenal, then oxidation and amidation are carried out to obtain piperine, and the yield is high. The key step namely palladium is used to catalyze oxidation-dehydrogenation is realized, and piperine can be synthesized efficiently and concisely. Compared with a conventional method, the operation is simple, the reaction yield is higher, the method is environmentally friendly, the yield is high,and the atom utilization rate is high.
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- A piperine quaternary ammonium salt derivative and its preparation method and application (by machine translation)
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The invention discloses a piperine quaternary ammonium salt derivative or its pharmaceutically acceptable hydrate, the formula (I) of the formula (II) is shown. Its preparation comprises the steps of: piperazine [...] acid salt with dihalogen serotonin reuptake reaction to make double-piperazine quaternary ammonium salt (III); pepper compounds prepared by first hydrolyzing the corresponding piperic acid, then with methanol to form methyl ester (IV) obtained; (IV) and (III) reaction, [...] (I); formula (I) (II) removing methylene [...]. The piperine quaternary ammonium salt derivatives of this invention with an anti-cancer effect. (by machine translation)
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Paragraph 0013
(2018/05/30)
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- Cyclodipeptide c(Orn-Pro) Conjugate with 4-Ethylpiperic Acid Abrogates Cancer Cell Metastasis through Modulating MDM2
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The present work describes the synthesis, characterization, and anticancer properties of c(Lys-Pro), P1; c(Orn-Pro), P2; and conjugates PA-c(Lys-Pro), C1; PA-c(Orn-Pro), C2; EPA-c(Lys-Pro), C3; and EPA-c(Orn-Pro), C4. Among all, conjugate C4 displays pote
- Shankar, Sudha,Faheem, Mir Mohd,Nayak, Debasis,Wani, Naiem Ahmad,Farooq, Saleem,Koul, Surrinder,Goswami, Anindya,Rai, Rajkishor
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p. 164 - 175
(2018/01/26)
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- Biology-oriented synthesis (BIOS) of piperine derivatives and their comparative analgesic and antiinflammatory activities
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Background: Serious side effects such as gastric intestinal ulcer, bleeding etc. are associated with most of the antiinflammatory and analgesic drugs. So, there is a need to search novel, potent, and safer antiinflammatory and analgesic drug. Method: Based on “biology-oriented synthesis approach”, piperine alkaloid was isolated from Piper nigrum L. and some derivatives of piperine having azomethine, sulfamoyl, propanoyl, acetamoyl and heterocyclic oxadiazole were synthesized. The structures of synthetic derivatives were confirmed by using different spectroscopic techniques such as1H-,13C-NMR, EI-MS, and IR. Melting points were also determined for all compounds. Piperine and its all the synthetic derivatives were subjected to comparative in vivo evaluation of analgesic and antiinflammatory activities at the oral dose of 6 mg/kg/day. Analgesic activity was evaluated by tail immersion, hot plate and acetic acid writhing methods. While, antiinflammatory activity was evaluated by carrageenan-induced paw inflammation. In silico studies of all synthetic compounds was also conducted on COX-2 and adenosine kinase enzymes. Results: A number of derivatives showed enhanced antiinflammatory and analgesic activities as compared to piperine and standard drug diclofenac. Conclusion: The newly identified molecules may serve as lead for the future research in connection of potent and safer antiinflammatory and analgesic drug candidate.
- Yasir, Ammar,Ishtiaq, Saiqa,Jahangir, Muhammad,Ajaib, Muhammad,Salar, Uzma,Khan, Khalid M.
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p. 269 - 280
(2018/05/23)
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- Structure–activity relationship of piperine and its synthetic amide analogs for therapeutic potential to prevent experimentally induced ER stress in vitro
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Endoplasmic reticulum (ER) is the key organelle involved in protein folding and maturation. Emerging studies implicate the role of ER stress in the development of chronic kidney disease. Thus, there is an urgent need for compounds that could ameliorate ER
- Hammad, Ayat S.,Ravindran, Sreenithya,Khalil, Ashraf,Munusamy, Shankar
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p. 417 - 428
(2017/08/29)
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- Medicinal compound pepper acid hexamethylene diamine and preparation process thereof
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The invention discloses a medicinal compound pepper acid hexamethylene diamine and a preparation process thereof. The pepper acid hexamethylene diamine has a chemical structural formula shown as below. The process comprises the following steps: (1) preparation of potassium piperate; (2) preparation of pepper acid; (3) preparation of ethyl piperate; and (4) preparation of pepper acid hexamethylene diamine. The invention has the following advantages: 1, piperic acid hexamethylene diamine is a semi-natural compound with significant hypolipidemic effect, and is a novel compound; the mice administration test proves that the pepper acid hexamethylene diamine has significant effect in reducing serum total cholesterol, triglyceride and the low density lipoprotein in animals with hyperlipemia; and no toxic reaction is found in the acute toxicity and cell experiments; 2, the pepper acid hexamethylene diamine as a substitute for statin drugs can create annual revenue of 2-5 billion U.S. dollars by just occupying 1/10 of the international market share, so as to achieve great economic benefits; and 3, the synthesis and production technology of pepper acid hexamethylene diamine have not been found home and abroad, and the invention is a pioneering innovation.
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- Synthesis, antimicrobial, antioxidant and nematicidal activity of (2E,4E)-5-(Benzo[d] [1,3]dioxol-5yl)penta-2,4-dienamides
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The amides of piperic acid have been synthesized via the condensation of piperic acid with amines. The structural characterization was done by IR, 1H-NMR, EI-MS and elemental analysis. The amides 3a-3o were evaluated for their biological activity. It has been found that among others the newly synthesized compound 3f, 3k, 3m, and 3o have great potential against root-knot nematode Meloidogyne incognita that usually affect tomato crop. These compounds exhibited 92, 96, 82 and 95% mortality rate at lethal concentration (LC50) 4.4, 3.4, 4.5 and 3.5 mg/mL, respectively. Conventionally used nematicide furadan was taken as standard. Compound 3h, 3c and, 3j exhibited significant anti-oxidant activities against 1,1-diphenylpicrylhydrazil (DPPH) radical with 80, 70 and 72% inhibition (EC50 = 625, 937 and 937.5 μg/mL), respectively. Ascorbic acid was used as standard. When tested for antimicrobial activity 3m was found to be the most active one showing zone of inhibition in the range of 18-30 mm against all tested microbial strains. Good biological activities of synthetic amides indicate their ability to behave as a good antimicrobial and nematicidal agent.
- Wahab, Aneela,Sultana, Amina,Khan, Khalid Mohammed,Sherwani, Sikandar K.,Perveen, Zeba,Taha, Muhammad,Karim, Aneela
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p. 1008 - 1014
(2016/01/12)
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- Synthesis and biological evaluation of piperic acid amides as free radical scavengers and αglucosidase inhibitors
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A series of piperic acid amides (4-24, 29, 30) were synthesized and their 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and α-glucosidase inhibitory activities were evaluated. Among the synthesized compounds, the amides 11, 13 and 15, which contain o-methoxyphenol, catechol or 5-hydroxyindole moieties, showed potent DPPH free radical scavenging activity (11: EC50 140 μM; 13: EC50 28 μM; 15: EC50 20 μM). The amides 10, 18 and 23 showed higher inhibitory activity of α-glucosidase (10: IC50 21 μM; 18: IC50 21 μM; 23: IC50 12 μM). These data suggest that the hydrophobicity of the conjugated amines is an important determinant of α-glucosidase inhibitory activity. In addition, the amides 13 and 15 showed both potent DPPH free radical scavenging activity and α-glucosidase inhibitory activity (13: IC50 46 μM; 15: IC50 46 μM). This is the first report identifying the DPPH free radical scavenging and α-glucosidase inhibitory activities of piperic acid amides and suggests that these amides may serve as lead compounds for the development of novel αglucosidase inhibitors with antioxidant activity.
- Takao, Koichi,Miyashiro, Takaki,Sugita, Yoshiaki
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p. 326 - 333
(2015/09/08)
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- NOVEL PIPERINE DERIVATIVES AND USES THEREOF
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The present invention provides novel piperine derivatives. The present pharmaceutical or food composition containing a piperine derivative as an active ingredient is very effective in preventing or treating metabolic diseases including obesity, diabetes, dyslipidemia, fatty liver and insulin resistance syndrome. Piperine derivatives of the present invention useful as pharmaceuticals compositions or functional food compositions has therapeutic efficacies for metabolic syndrome selected from the group consisting of obesity, diabetes, hyperlipidemia, fatty liver and insulin resistance syndrome, and also suppress the differentiation of progenitor cells and reduce the accumulation of triglycerides.
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Paragraph 0067; 0068
(2015/01/06)
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- NOVEL PIPERINE DERIVATIVE AND USE THEREFOR
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The present invention provides novel piperine derivatives. The present pharmaceutical or food composition containing a piperine derivative as an active ingredient is very effective in preventing or treating metabolic diseases including obesity, diabetes,
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Paragraph 0051; 0052
(2015/01/16)
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- Natural-product-based insecticidal agents 14. Semisynthesis and insecticidal activity of new piperine-based hydrazone derivatives against Mythimna separata Walker in vivo
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In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, twenty-six new piperine-based hydrazone derivatives were synthesized from piperine, an alkaloid isolated from Piper nigrum Linn. The single-crystal structures of 6c, 6q and 6w were unambiguously confirmed by X-ray crystallography. Their insecticidal activity was evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 6b, 6i and 6r, the final mortality rates of which, at the concentration of 1 mg/mL, were 62.1%, 65.5% and 65.5%, respectively, exhibited more pronounced insecticidal activity compared to toosendanin at 1 mg/mL, a commercial botanical insecticide isolated from Melia azedarach. It suggested that introduction of the substituents at the C-2 position on the phenyl ring of the hydrazone derivatives was important for their insecticidal activity.
- Qu, Huan,Yu, Xiang,Zhi, Xiaoyan,Lv, Min,Xu, Hui
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supporting information
p. 5552 - 5557
(2013/10/01)
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- Design, synthesis and trypanocidal evaluation of novel 1,2,4-triazoles-3- thiones derived from natural piperine
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The work reported herein describes the synthesis and the assessment of the trypanocidal activity of thirteen new 1,2,4-triazole-3-thiones obtained from natural piperine, the main constituent of the dry fruits of Piper nigrum. It is part of a research program aiming to use abundant and easily available natural products as starting materials for the design and synthesis of new molecules potentially useful as antiparasitic drugs. The variously substituted triazole derivatives were synthesized from the natural amide in four steps with the use of microwave irradiation on overall yields ranging from 32% to 51%. The cyclohexyl substituted derivative showed the best trypanocidal profile on proliferative forms of Trypanosoma cruzi (Y strain), with IC50s = 18.3 and 8.87 μM against epimastigotes and amastigotes, respectively.
- Franklim, Tatiany Nunes,Freire-De-Lima, Leonardo,De Nazareth Sa Diniz, Julliana,Previato, Jose Osvaldo,Castro, Rosane Nora,Mendonca-Previato, Lucia,De Lima, Marco Edilson Freire
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p. 6366 - 6382
(2013/07/26)
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- Sodium Piperonyl Pentadienoate and Use of the Same for Lowering Blood Lipid
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The invention discloses sodium piperonyl pentadienoate, and pharmaceutical compositions or health care products containing sodium piperonyl pentadienoate, as well as a method of the preparation of sodium piperonyl pentadienoate, and the use of sodium piperonyl pentadienoate for lowering blood lipid, including the use of sodium piperonyl pentadienoate in the preparation of medicaments or health care products for lowering serum total cholesterol, lowering low density lipoprotein cholesterol, lowering triglyceride as well as preventing decrease of high density lipoprotein cholesterol.
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- Synthesis, anticancer and antibacterial activities of piperine analogs
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A series of piperine analogs were synthesized by the condensation of piperic acid with different aminoacids and substituted aniline. The synthesized compounds (4a-4e) were evaluated for their anticancer activity against human cancer cell lines (MCF-7, Breast Cancer cell line, and Hela cervix cell line) and antibacterial activity against human pathogens (Escherichia coli, Klebsiella pneumoniae, Salmonella typhi, Shigella dysenteriae, Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa). The efficacies of the synthesized compounds were superior to those of piperine in all tested human cancer cell lines. Among the tested conjugates, 4c showed significant anticancer activity against Hela cervix cell line with IC50 of 0.736 μmol and 4a showed significant activity against breast cancer cell line. The antibacterial activity of the tested compounds was also found to be superior to that of piperine. The approach is novel as the abundantly available natural product piperine is utilized as precursor for the synthesis of new potential antimicrobial and anticancer agents.
- Umadevi, Parimi,Deepti, Kolli,Venugopal, Durvasula V. R.
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p. 5466 - 5471
(2013/12/04)
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- Synthesis of piperine-amino acid ester conjugates and study of their cytotoxic activities against human cancer cell lines
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A series of piperine-amino acid ester conjugates (4a-4r) were synthesized under mild conditions and screened for their cytotoxic activities against a panel of human cancer cell lines (IMR-32, MCF-7, PC-3, DU-145, Colo-205, and Hep-2). The parent compound
- Rao, V. Rama Subba,Suresh,Rao, R. Ranga,Babu, K. Suresh,Chashoo,Saxena,Rao, J. Madhusudana
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experimental part
p. 38 - 46
(2012/06/01)
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- Synthesis and inhibitory effect of piperine derivates on monoamine oxidase
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A series of piperine derivates (1-19) have been designed, synthesized and evaluated in vitro for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. It is worth noting that most of the small amine moieties substituted on the piperidine ring proved to be potent and selective inhibitors of MAO-B rather than of MAO-A. 5-(3,4-methylenedioxyphenyl)-2E,4E-pentadienoic acid n-propyl amide (3) showed the greatest MAO-B inhibitory activity (IC 50(MAO-B) = 0.045 μM) and good selectivity (IC50(MAO-A) = 3.66 μM). The conjugated double bond and carbonyl group of piperine are proved to be an essential feature for piperine and related alkylamides to exhibit MAO-inhibitory activity. Binding mode of the titled compounds was predicted using FlexX algorithm. The design and optimization of novel small molecule monoamine oxidase inhibitors will be guided by the results of this report.
- Mu, Li-Hua,Wang, Bo,Ren, Hao-Yang,Liu, Ping,Guo, Dai-Hong,Wang, Fu-Meng,Bai, Lin,Guo, Yan-Shen
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scheme or table
p. 3343 - 3348
(2012/06/29)
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- NOVEL PIPERINE DERIVATIVES AS GABA-A RECEPTORS MODULATORS
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The present invention encompasses novel piperin compounds of general formula (I) wherein R1, R2, R3, m and n are defined as in claim 1, which are suitable for the prevention and/or treatment of diseases mediated by modulation of GABAA receptor and the use thereof for preparing a medicament having the above mentioned properties.
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Page/Page column 23
(2011/07/30)
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- Synthesis and Antileishmanial activity of Piperoyl-Amino Acid Conjugates
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Based on reported antileishmanial activity of naturally occurring alkaloid piperine and amino acid esters,their conjugates were synthesized by the hydrolysis of piperine to piperic acid followed by reaction with amino acid methyl esters. These conjugates were further converted to compounds with free carboxyl group and those with reduced double bonds. The synthesized compounds were evaluated for activity against promastigote and amastigote forms of L. donovani in vitro. All the compounds showed better activity than either piperine or the amino acid methyl esters. Piperoyl-valine methyl ester was the most active compound showing an IC50 of 0.075 mM against the amastigotes. Two active compounds were evaluated for in vivo activity in golden hamster model of leishmaniasis.
- Singh, Inder Pal,Jain, Shreyans Kumar,Kaur, Amandeep,Singh, Sukhvinder,Kumar, Rajender,Garg, Prabha,Sharma, Shyam Sundar,Arora, Sunil Kumar
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experimental part
p. 3439 - 3445
(2010/08/19)
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- In vitro TRPV1 activity of piperine derived amides
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A series of natural and synthetic piperine amides were evaluated for activity on the human TRPV1 expressed in HEK293 cells. The agonistic effect of piperine amides was mainly dependent on the length of the carbon chain. Structural changes of double bonds and stereochemistry in the aliphatic chain of these compounds did not change their potency or efficacy, indicating that increased rigidity or planarity of the piperine structure does not affect the activity. The opening of the methylenedioxy ring or changes in the heterocyclic ring of the piperine molecule reduced or abolished activity. Furthermore, inactive compounds did not display functional antagonistic activity.
- Correa, Edwin Andrés,H?gest?tt, Edward D.,Sterner, Olov,Echeverri, Fernando,Zygmunt, Peter M.
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experimental part
p. 3299 - 3306
(2010/07/04)
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- Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: Chemical and biological studies
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We herein describe the synthesis and characterization of nine new 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine. We evaluate their toxic effects against the different evolutive forms of Trypanosoma cruzi, and the host cell (murine macrophages). The results obtained show that mesoionic hydrochloride MI possesses the best activity profile. Compound MI may be a prototype for use in the development of a new chemotherapeutic agent with high efficiency, which may be employed in the treatment of Chagas' disease.
- da Silva Ferreira, Welisson,Freire-de-Lima, Leonardo,Saraiva, Victor Barbosa,Alisson-Silva, Frederico,Mendonca-Previato, Lucia,Previato, Jose Osvaldo,Echevarria, Aurea,de Lima, Marco Edilson Freire
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p. 2984 - 2991
(2008/09/19)
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- Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors
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Based on our recent findings that piperine is a potent Staphylococcus aureus NorA efflux pump inhibitor (EPI), 38 piperine analogs were synthesized and bioevaluated for their EPI activity. Twenty-five of them were found active with potentiating activity equivalent or more than known EPIs like reserpine, carsonic acid and verapamil. The inhibitory mechanism of the compounds was confirmed by efflux inhibition assay using ethidium bromide as NorA substrate. The present communication describes the synthesis, bioevaluation and structure related activity of these efflux pump inhibitors.
- Sangwan, Payare L.,Koul, Jawahir L.,Koul, Surrinder,Reddy, Mallepally V.,Thota, Niranjan,Khan, Inshad A.,Kumar, Ashwani,Kalia, Nitin P.,Qazi, Ghulam N.
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experimental part
p. 9847 - 9857
(2009/04/11)
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