56019-71-7Relevant articles and documents
Synthesis, in vitro and in silico anti-bacterial analysis of piperine and piperic ester analogues
Sivashanmugam, Arthi,Velmathi, Sivan
, p. 19 - 29 (2021/04/27)
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.
Mild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones
Subramani, Muthuraman,Rajendran, Saravana Kumar
, p. 3677 - 3686 (2019/06/08)
Amides are indispensable building blocks of biological systems, pharmaceuticals, and materials. We report a highly selective method for the synthesis of amides via transamidation process. Transamidation of N-acyl-2-piperidones with a broad range of amines is demonstrated under exceedingly mild and metal-free reaction condition that relies on the amide bond twist to weaken the amidic resonance. Transamidation proceeds under the neat condition at room temperature, in short reaction times (30–90 min) with good yields. Considerable variation is tolerated with both amine and imide substrates. Of note, amines bearing carboxylic acids (glycine and serine) and hydroxyl groups (dopamine, tyramine, etc.) are well tolerated which are otherwise problematic under the metal-catalyzed protocol. Our current method is applicable for transamidation of both alkyl and aryl-N-acyl-2-piperidones. The practical value of the method is highlighted by the synthesis of four natural product amide alkaloids in high yields under mild reaction conditions. In the absence of nucleophilic amines, N-acyl-2-piperidones undergoes esterification with EtOH at elevated temperature. Single crystal X-ray analysis of an N-acyl-2-piperidone shows amide bond twist, τ = –20.39° and pyramidalization, χN = –11.73°. This weakens the amidic conjugation and might be the factor controlling the reactivity and selectivity of these imides. We envision that the N-acyl-2-piperidone scaffold would be useful in the synthesis of pharmaceuticals and materials.
Biology-oriented synthesis (BIOS) of piperine derivatives and their comparative analgesic and antiinflammatory activities
Yasir, Ammar,Ishtiaq, Saiqa,Jahangir, Muhammad,Ajaib, Muhammad,Salar, Uzma,Khan, Khalid M.
, p. 269 - 280 (2018/05/23)
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.
New potent and selective polyfluoroalkyl ketone inhibitors of GVIA calcium-independent phospholipase A2
Magrioti, Victoria,Nikolaou, Aikaterini,Smyrniotou, Annetta,Shah, Ishita,Constantinou-Kokotou, Violetta,Dennis, Edward A.,Kokotos, George
supporting information, p. 5823 - 5829 (2013/09/12)
Group VIA calcium-independent phospholipase A2 (GVIA iPLA 2) has recently emerged as an important pharmaceutical target. Selective and potent GVIA iPLA2 inhibitors can be used to study its role in various neurological diso
Synthesis and inhibitory effect of piperine derivates on monoamine oxidase
Mu, Li-Hua,Wang, Bo,Ren, Hao-Yang,Liu, Ping,Guo, Dai-Hong,Wang, Fu-Meng,Bai, Lin,Guo, Yan-Shen
, p. 3343 - 3348 (2012/06/29)
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.
A simple synthesis of piperlonguminine
Seung, Ho Lee,Dong, Hyun Kim,Jeong, Ah Kim,Jahng, Yurngdong
, p. 407 - 410 (2007/10/03)
A simple and practical method for the synthesis of an alkaloid piperlongumine, an efficient inhibitor of α-melanocyte stimulating hormone, was established by employing Wadsworth-Horner modified Wittig reaction as a key step.
Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation
Venkatasamy, Radhakrishnan,Faas, Laura,Young, Antony R.,Raman, Amala,Hider, Robert C.
, p. 1905 - 1920 (2007/10/03)
A wide range of piperine analogues has been synthesised in order to undertake a structure-activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2E,4E-dienoic acid methyl ester (5a), 1-E,E-piperinoyl-isobutylamine (4f) and 1-(3,4- methylenedioxyphenyl)-pentanoic acid cyclohexyl amide (20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds.
Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg-Baecklund reaction
Li, Yang,Zhang, Yu,Huang, Zhi,Cao, Xiaoping,Gao, Kun
, p. 622 - 630 (2007/10/03)
A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a-1n by the recently developed one-flask Ramberg-Baecklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of sulfide 6 gave the corresponding sulfone 2. Treatment of the sulfone 2 with the dibromodifluoromethane in the presence of alumina-supported potassium hydroxide in dichloromethane solution afforded unsaturated amide alkaloids 1a-1n. To the best of our knowledge, the synthesis of 1e and 1i was reported for the first time.
Amide derivatives and 5-lipoxygenase inhibitors containing the same as an active ingredient
-
, (2008/06/13)
According to the invention, there are provided novel amide derivatives and 5-lipoxygenase inhibitors containing the same as an effective ingredient. The above-mentioned compounds of the invention have been demonstrated to posses 5-lipoxygenase-inhibiting activities. These compounds can inhibit the production of leucotrienes such as LTC4 and LTD4 which are allergy-inducing factors by inhibiting the activity of 5-lipoxygenase. Accordingly, the amide derivatives can be used as 5-lipoxygenase inhibitors effective for allergic asthma, allergic rhinitis and the like.
