20890-16-8Relevant academic research and scientific papers
Antimicrobial activity of some N-alkyl substituted of (E)-4-azachalconium and (E)-3'-hydroxy-4-azachalconium bromides.
Nowakowska, Zdzislawa,Wyrzykiewicz, Elzbieta,Kedzia, Bogdan
, p. 657 - 661 (2002)
Twelve new N-substituted (E)-azachalconium bromides were synthesized and tested for antimicrobial and antifungal activities. Compounds 5c, 5d and 5h-5l showed very good antimicrobial activity against Staphylococcus aureus, Enterococcusfaecalis as well as
Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds
Nagendra Chowdary,Umashankara,Dinesh,Girish,Ramesha Baba
, p. 45 - 50 (2018/12/11)
A series of 16 chalcone compounds were synthesized by Claisen-Schmidt condensation of various aldehydes with acetophenone using KOH as a base in ethanol. The reaction affords the desired products in good yields. Then all the 16 compounds were converted into pyrazoles by treating with hydrazine hydrate in ethanol under reflux condition. Both chalcones and pyrazoles were screened for their in vitro antibacterial (Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa) and antifungal (Aspergillus flavus, Chrysosporium keratinophilum and Candida albicans) activity. Biological activities of these compounds were compared with those of commercially available antibiotic ampicillin and antifungal agent miconazole. Pyrazoles were found to be most active and effective than corresponding chalcones for antimicrobial activity. Out of the 7 pyrazole compounds tested for antibacterial and antifungal activity, 5 compounds, 4h, 4j, 4l, 4m and 4n are turned out to be potent antimicrobial agents. Therefore these derivatives could serve as a highly promising molecules for further development.
High-Throughput Screening and Hit Validation of Extracellular-Related Kinase 5 (ERK5) Inhibitors
Myers, Stephanie M.,Bawn, Ruth H.,Bisset, Louise C.,Blackburn, Timothy J.,Cottyn, Betty,Molyneux, Lauren,Wong, Ai-Ching,Cano, Celine,Clegg, William,Harrington, Ross. W.,Leung, Hing,Rigoreau, Laurent,Vidot, Sandrine,Golding, Bernard T.,Griffin, Roger J.,Hammonds, Tim,Newell, David R.,Hardcastle, Ian R.
supporting information, p. 444 - 455 (2016/08/16)
The extracellular-related kinase 5 (ERK5) is a promising target for cancer therapy. A high-throughput screen was developed for ERK5, based on the IMAP FP progressive binding system, and used to identify hits from a library of 57-617 compounds. Four distinct chemical series were evident within the screening hits. Resynthesis and reassay of the hits demonstrated that one series did not return active compounds, whereas three series returned active hits. Structure-activity studies demonstrated that the 4-benzoylpyrrole-2-carboxamide pharmacophore had excellent potential for further development. The minimum kinase binding pharmacophore was identified, and key examples demonstrated good selectivity for ERK5 over p38α kinase.
Application of bis(oxazoline) in asymmetric β-amination of chalcones
Deng, Tao,Wang, Hongjun,Cai, Chun
supporting information, p. 102 - 105 (2015/02/19)
An effective enantioselective β-amination of chalcones with N-bromosuccinimide into β-imidoketones using a bis(oxazoline) ligand is described. A wide variety of β-imidoketone derivatives containing various functional groups can be obtained with high enantioselectivities. The products are highly valuable molecules regarding their vast applications as building blocks of drugs and biologically active compounds.
Chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal with aldehydes and ketones
Zhang, Jiantao,Xu, Jiaxi
, p. 1733 - 1739 (2013/10/21)
The chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal (1) with aldehydes and ketones in the presence of Et3N was investigated. The results indicate that 1 reacts with aromatic aldehydes with weak electron-donating substituents and cyclic ketones under formation of 6-phenyl-4H-1,3-dioxin-4-one derivatives. However, it reacts with aromatic aldehydes with electron-withdrawing substituents to yield 1,3-diaryl-3-hydroxypropan-1-ones, accompanied by chalcone derivatives in some cases. It did not react with linear ketones, aliphatic aldehydes, and aromatic aldehydes with strong electron-donating substituents. A mechanism for the formation of 1,3-diaryl-3-hydroxypropan-1-ones and chalcone derivatives is proposed. We also tried to react 1 with other unsaturated compounds, including various olefins and nitriles, and cumulated unsaturated compounds, such as N,N′-dialkylcarbodiimines, phenyl isocyanate, isothiocyanate, and CS2. Only with N,N′-dialkylcarbodiimines, the expected cycloaddition took place. Copyright
Ferrocenyl chalcones versus organic chalcones: A comparative study of their nematocidal activity
Attar, Saeed,O'Brien, Zachary,Alhaddad, Hasan,Golden, Melissa L.,Calderón-Urrea, Alejandro
supporting information; experimental part, p. 2055 - 2073 (2011/04/27)
A series of 30 organic chlacones and 33 ferrocenyl (Fc) chalcones were synthesized and characterized by melting point, elemental analysis, spectroscopy (1H NMR and FTIR) and, in two cases, by X-ray crystallography. The biological activity of each compound (10-4 M in DMSO) against the model nematode Caenorhabditis elegans was examined in terms of % mortality (percent nematodes that died) and % fecundity (percent nematodes that reproduced) and compared to that obtained for the control medium (1% DMSO) over a 14-day period. Detailed conformational analyses for two Fc-chalcones (studied also by X-ray crystallography) were performed via molecular modeling studies. In general, the organic chalcones were found to be less polar than their Fc analogs. Some structure-activity relationships (SARs) were determined: (a) The nematocidal activities of the organic chalcones in this series were found to be much greater than those of their ferrocenyl analogs. (b) The position of the carbonyl group played a central role in the biological activity of both classes of chalcones studied. (c) For both classes of chalcones, lipophilicity of a compound seemed to play a significant role in its nematocidal activity. (d) The planarity of a ferrocenyl-chlacone seems to play a role in its activity.
Cooperative N -heterocyclic carbene/lewis acid catalysis for highly stereoselective annulation reactions with homoenolates
Cardinal-David, Benoit,Raup, Dustin E. A.,Scheidt, Karl A.
supporting information; experimental part, p. 5345 - 5347 (2010/07/03)
A new approach that takes advantage of N-heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivity and enantioselectivity. T
Solution-phase parallel synthesis of substituted chalcones and their antiparasitary activity against Giardia lamblia
Montes-Avila, Julio,Diaz-Camacho, Sylvia P.,Sicairos-Felix, Josefina,Delgado-Vargas, Francisco,Rivero
experimental part, p. 6780 - 6785 (2009/12/06)
A library of 25-membered chalcones was prepared by parallel synthesis. Substituted acetophenones and benzaldehydes were condensed using the Claisen-Schmidt base-catalyzed aldol condensation. Several chalcones showed in vitro antiparasitic activity against Giardia lamblia. The highest activity observed for the IC50 values were 12.72, 15.05 and 15.31 μg/mL, respectively; these are potential leads for the development of antigiardial compounds.
2,4,6-Trisubstituted pyridines: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship
Basnet, Arjun,Thapa, Pritam,Karki, Radha,Na, Younghwa,Jahng, Yurngdong,Jeong, Byeong-Seon,Jeong, Tae Cheon,Lee, Chong-Soon,Lee, Eung-Seok
, p. 4351 - 4359 (2008/03/12)
Designed and synthesized were a series of pyridines substituted at 2, 4, and 6 positions with various 5- or 6-memberd heteroaromatics as antitumor agents. They were evaluated their topoisomerase I and II inhibitory activities along with cytotoxicities against several human cancer cell lines. Among the prepared compounds, 10-20 showed significant topoisomerase I or II inhibitory activities, and 21-26 showed considerable cytotoxicities against several human cancer cell lines. Structure-activity relationship study indicates that 4′-pyridine at 6-position of central pyridine plays a key role in biological activity.
Coupling-isomerization-Stetter and coupling-isomerization-Stetter-Paal- Knorr sequences - A multicomponent approach to furans and pyrroles
Braun, Roland U.,Mueller, Thomas J. J.
, p. 2391 - 2406 (2007/10/03)
2,3,5-Trisubstituted furans 6 and 1,2,3,5-tetrasubstituted pyrroles 8 can be synthesized in good yields in a one-pot three-step three- or four-component process by a coupling-isomerization-Stetter-Paal-Knorr sequence of an electron-poor (hetero)aryl halid
