20426-49-7Relevant academic research and scientific papers
Orthorhombic polymorphs of 1-phenyl-3-(3-Hydroxyphenyl)-2-propen-1-one
Jennings, Geremia,Smith, Mark D.,Kuang, Shan-Ming,Mark Hodges,Tyrell, John,Thomas Williamson,Seaton, Pamela
, p. 159 - 164 (2012)
Chalcones, 1,3-diphenyl-2-propene-1-ones, exist naturally and synthetically, and are characterized by the linkage of two aromatic rings joining a three carbon α-β-unsaturated carbonyl entity. We report the observation of two new polymorphs of a hydroxy ch
Chiral pincer-like compound and palladium or nickel complex and synthesis method thereof
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Paragraph 0061-0062, (2021/01/15)
The invention relates to a chiral pincer-like compound and a palladium or nickel complex and a synthetic method thereof in the field of catalysts, the chemical formulas of the chiral pincer-like compound and the palladium or nickel complex are shown as (I
Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents
Zhong, Hui,Zhou, Jia,An, Xiao-Hong,Hua, Ying-Rong,Lai, Yi-Fan,Zhang, Rui,Ahmad, Owais,Zhang, Ye,Shang, Jing
, p. 523 - 533 (2019/04/01)
A bioactive component, 2′,3,4,4′-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1–RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.
Structure-activity relationship with pyrazoline-based aromatic sulfamates as carbonic anhydrase isoforms I, II, IX and XII inhibitors: Synthesis and biological evaluation
Moi, Davide,Nocentini, Alessio,Deplano, Alessandro,Balboni, Gianfranco,Supuran, Claudiu T.,Onnis, Valentina
, (2019/08/30)
Four new series of aromatic sulfamates were synthesized and investigated for the inhibition of four human (h) isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), hCA I, II, IX, and XII. The reported derivatives, obtained by a sulfamoylation reaction of the corresponding phenolic precursors, bear 3,5-diarylpyrazoline moieties as spacers between the benzenesulfamate fragment which binds the zinc ion from the active site, and the tail of the inhibitor. Pyrazolines are biologically privileged scaffolds, endowed with versatile biological activity, such as an anti-proliferative action. The derivatives were tested for the inhibition of the cytosolic, hCA I and II (off target isoforms) and the trans-membrane, tumor-associated hCA IX and XII enzymes (anticancer drug targets). Generally, hCA I was not effectively inhibited, whereas many low nanomolar inhibitors were evidenced against hCA II (KIs in the range of 0.42–90.1 nM), IX (KIs in the range of 0.72–63.6 nM), and XII (KIs in the range of 0.88–85.2 nM). The best substitution fragments at the pyrazoline ring included for CA II a 4-sulfamic group on the 3-aryl and halogens on the 5-aryl or a methoxy group on the 3-aryl and a 4-sulfamate group on the 5-aryl; for CA IX and CA XII they included the sulfamic group on the 3- or 4-position of the 5-aryl and an electronwithdrawing group on the 4-postion of the 3-aryl ring.
Design, Synthesis, and Biological Evaluation of Pyrazoline-Based Hydroxamic Acid Derivatives as Aminopeptidase N (APN) Inhibitors
Cao, Jiangying,Zang, Jie,Ma, Chunhua,Li, Xiaoguang,Hou, Jinning,Li, Jin,Huang, Yongxue,Xu, Wenfang,Wang, Binghe,Zhang, Yingjie
supporting information, p. 431 - 436 (2018/02/21)
Aminopeptidase N (APN) has been recognized as a target for anticancer treatment due to its overexpression on diverse malignant tumor cells and association with cancer invasion, metastasis and angiogenesis. Herein we describe the synthesis, biological evaluation, and structure–activity relationship study of two new series of pyrazoline analogues as APN inhibitors. Among these compounds, 5-(2-(2-(hydroxyamino)-2-oxoethoxy)phenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (compound 13 e) showed the best APN inhibition with an IC50 value of 0.16±0.02 μm, which is more than one order of magnitude lower than that of bestatin (IC50=9.4±0.5 μm). Moreover, compound 13 e was found to inhibit the proliferation of diverse carcinoma cells and to show potent anti-angiogenesis activity. At the same concentration, compound 13 e presents significantly higher anti-angiogenesis activity than bestatin in human umbilical vein endothelial cells (HUVECs) capillary tube formation assays. The putative binding mode of 13 e in the active site of APN is also discussed.
QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase
Yaeghoobi, Marzieh,Frimayanti, Neni,Chee, Chin Fei,Ikram, Kusaira K.,Najjar, Belal O.,Zain, Sharifuddin M.,Abdullah, Zanariah,Wahab, Habibah A.,Rahman, Noorsaadah Abd.
, p. 2133 - 2142 (2016/10/25)
Thirty three chalcones were synthesized and tested on viral H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure?activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure?activity relationships of these chalcone derivatives. Result from the 2D-quantitative structure?activity relationship model indicates that electrostatic parameter enhanced bioactivity of the chalcones while steric substituents diminished their potency as H1N1 neuraminidase inhibitors. 3D-quantitative structure?activity relationship model showed the importance of the position of the hydroxyl group in chalcone derivatives which can influence on hydrophobicity, hydrogen bond donor and aromatic ring features that enhance the biological activity. Finally, docking studies showed that chalcones MC8 and MC16 with low C docker interaction energies and higher numbers of hydrogen bonding have better inhibitory activity against viral H1N1 neuraminidase.
Synthesis and screening of antimicrobial activity of novel pyrrolylpyrazole derivatives
Hallikeri,Joshi, Shrinivas D.,Kumar, Devendra,Kulkarni,Selvam, Theivendren Paneer
, p. 261 - 264 (2019/01/21)
Novel pyrrolyl-pyrazole derivatives (5a-k) were synthesized by reacting substituted chalcones (3a-k) and 4-pyrrol-1-yl benzoic acid hydrazide (4) in ethanol. Purity of newly synthesized compounds were confirmed by TLC and melting point. The structures of all newly synthesized compounds were confirmed by spectral study such as IR, 1H NMR and Mass spectroscopy. The title compounds were screened for their antibacterial and antitubercular activities.
Synthesis and evaluation of chalcone derivatives as inhibitors of neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species
Bukhari, Syed N. A.,Tajuddin, Yasmin,Benedict, Vannessa J.,Lam, Kok W.,Jantan, Ibrahim,Jalil, Juriyati,Jasamai, Malina
, p. 198 - 206 (2014/02/14)
Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti-inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol- and lucigenin-based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4-methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators. Chalcone derivatives were synthesised and evaluated for their inhibitory effects on PMNs chemotaxis, phagocytosis and intracellular and extracellular ROS productions. It was observed that phenyl-4-methylaminoethanol and dimethoxy substituents contributed to these effects.
Evaluation of the radical scavenging activity of a series of synthetic hydroxychalcones towards the DPPH radical
Todorova, Iva T.,Batovska, Daniela I.,Stamboliyska, Bistra A.,Parushev, Stoyan P.
body text, p. 491 - 497 (2012/01/06)
Sixteen hydroxychalcones were synthesized in sufficient purity by the Claisen-Schmidt condensation between appropriate acetophenones and aromatic aldehydes. All the compounds were evaluated for their ability to scavenge the stable free 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Important structure-activity relationships were observed that strongly contribute to the knowledge for the design of DPPH radical scavenging chalcones. Relevant theoretical parameters were computed in an attempt to understand and explain the obtained experimental results.
Synthesis and biological evaluation of anti-inflammatory activity of 1,3 diphenyl propenone derivatives
Yadav, Hardwari L.,Gupta, Pankaj,Pawar,Singour,Patil
experimental part, p. 461 - 465 (2012/04/04)
A series of five chalcone derivatives were synthesized by Claisen-Schmidt condensation of acetophenone with appropriately substituted benzaldehyde in the presence of aqueous alkali. The synthesized compounds were characterized by their IR, NMR, and Mass s
