1058712-24-5Relevant articles and documents
Synthesis and Spectroscopic Analysis of Piperine- And Piperlongumine-Inspired Natural Product Scaffolds and Their Molecular Docking with IL-1β and NF-κB Proteins
Cornelio, Marinonio L.,Jones, Alan M.,Le Duff, Cécile S.,Povinelli, Ana Paula R.,Tang, Bridget,Zazeri, Gabriel
, (2020/07/02)
Inspired by the remarkable bioactivities exhibited by the natural products, piperine and piperlongumine, we synthesised eight natural product-inspired analogues to further investigate their structures. For the first time, we confirmed the structure of the key cyclised dihydropyrazolecarbothioamide piperine analogues including the use of two-dimensional (2D) 15N-based spectroscopy nuclear magnetic resonance (NMR) spectroscopy. Prior investigations demonstrated promising results from these scaffolds for the inhibition of inflammatory response via downregulation of the IL-1β and NF-κB pathway. However, the molecular interaction of these molecules with their protein targets remains unknown. Ab initio calculations revealed the electronic density function map of the molecules, showing the effects of structural modification in the electronic structure. Finally, molecular interactions between the synthesized molecules and the proteins IL-1β and NF-κB were achieved. Docking results showed that all the analogues interact in the DNA binding site of NF-κB with higher affinity compared to the natural products and, with the exception of 9a and 9b, have higher affinity than the natural products for the binding site of IL-1β. Specificity for the molecular recognition of 3a, 3c and 9b with IL-1β through cation–π interactions was determined. These results revealed 3a, 3c, 4a, 4c and 10 as the most promising molecules to be evaluated as IL-1β and NF-κB inhibitors.
Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature
Tamuli, Kashyap J.,Sahoo, Ranjan K.,Bordoloi, Manobjyoti
supporting information, p. 20956 - 20965 (2020/12/31)
Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.
Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum
Bertoldo, Jean Borges,Chiaradia-Delatorre, Louise Domeneghini,Mascarello, Alessandra,Leal, Paulo César,Cordeiro, Marlon Norberto Sechini,Nunes, Ricardo José,Sarduy, Emir Salas,Rosenthal, Philip Jon,Terenzi, Hernán
, p. 299 - 307 (2015/04/14)
Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkyl-esters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5±0.8μM, 9.5±0.2μM and 4.9±1.3μM, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.
Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents
Monga, Vikramdeep,Goyal, Kamya,Steindel, Mario,Malhotra, Manav,Rajani, Dhanji P.,Rajani, Smita D.
, p. 2019 - 2032 (2014/05/06)
A series of chalcones (1-8) were prepared by Claisen-Schmidt condensation of 3-nitroacetophenone with various aldehydes. These chalcones on cyclization with hydrazine hydrate in the presence of glacial acetic acid, hydrazine hydrate in absolute ethanol an
A novel and efficient direct aldol condensation from ketones and aromatic aldehydes catalyzed by proline-TEA through a new pathway
Wang, Jun-feng,Lei, Meng,Li, Qin,Ge, Ze-mei,Wang, Xin,Li, Run-tao
experimental part, p. 4826 - 4833 (2009/10/02)
A novel and efficient direct aldol condensation from various ketones and a wide range of aldehydes was catalyzed by l-proline-TEA (triethylamine) in MeOH at room temperature, affording the corresponding (E)-α,β-unsaturated ketones in excellent yields. By
Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
Chiaradia, Louise Domeneghini,Mascarello, Alessandra,Purificacao, Marcela,Vernal, Javier,Cordeiro, Marlon Norberto Sechini,Zenteno, Maria Emilia,Villarino, Andrea,Nunes, Ricardo Jose,Yunes, Rosendo Augusto,Terenzi, Hernan
supporting information; experimental part, p. 6227 - 6230 (2009/06/30)
In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were ob
