1475-91-8Relevant academic research and scientific papers
Structure-Activity Relationship and Pharmacokinetic Studies of 1,5-Diheteroarylpenta-1,4-dien-3-ones: A Class of Promising Curcumin-Based Anticancer Agents
Wang, Rubing,Chen, Chengsheng,Zhang, Xiaojie,Zhang, Changde,Zhong, Qiu,Chen, Guanglin,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi,Chen, Qiao-Hong
, p. 4713 - 4726 (2015/06/25)
Forty-three 1,5-diheteroaryl-1,4-pentadien-3-ones were designed as potential curcumin mimics, structurally featuring a central five-carbon dienone linker and two identical nitrogen-containing aromatic rings. They were synthesized using a Horner-Wadsworth-Emmons reaction as the critical step and evaluated for their cytotoxicity and antiproliferative activities toward both androgen-insensitive and androgen-sensitive prostate cancer cell lines and an aggressive cervical cancer cell line. Most of the synthesized compounds showed distinctly better in vitro potency than curcumin in the four cancer cell lines. The structure-activity data acquired from the study validated (1E,4E)-1,5-dihereroaryl-1,4-pentadien-3-ones as an excellent scaffold for in-depth development for clinical treatment of prostate and cervical cancers. 1-Alkyl-1H-imidazol-2-yl, ortho pyridyl, 1-alkyl-1H-benzo[d]imidazole-2-yl, 4-bromo-1-methyl-1H-pyrazol-3-yl, thiazol-2-yl, and 2-methyl-4-(trifluoromethyl)thiazol-5-yl were identified as optimal heteroaromatic rings for the promising in vitro potency. (1E,4E)-1,5-Bis(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one, featuring thiazole rings and trifluoromethyl groups, was established as the optimal lead compound because of its good in vitro potency and attractive in vivo pharmacokinetic profiles. (Chemical Equation Presented).
A remarkable cis- and trans-spanning dibenzylidene acetone diphosphine chelating ligand (dbaphos)
Jarvis, Amanda G.,Sehnal, Petr E.,Bajwa, Somia E.,Whitwood, Adrian C.,Zhang, Xiangbiao,Cheung, Man Sing,Lin, Zhenyang,Fairlamb, Ian J. S.
supporting information, p. 6034 - 6043 (2013/06/27)
A multidentate and flexible diolefin-diphosphine ligand, based on the dibenzylidene acetone core, namely dbaphos (1), is reported herein. The ligand adopts an array of different geometries at Pt, Pd and Rh. At PtII the dbaphos ligand forms cis- and trans-diphosphine complexes and can be defined as a wide-angle spanning ligand. 1H NMR spectroscopic analysis shows that the β-hydrogen of one olefin moiety interacts with the PtII centre (an anagostic interaction), which is supported by DFT calculations. At Pd0 and RhI, the dbaphos ligand exhibits both olefin and phosphine interactions with the metal centres. The Pd0 complex of dbaphos is dinuclear, with bridging diphosphines. The complex exhibits the coordination of one olefin moiety, which is in dynamic exchange (intramolecular) with the other "free" olefin. The Pd0 complex of dbaphos reacts with iodobenzene to afford trans-[PdII(dbaphos)I(Ph)]. In the case of RhI, dbaphos coordinates to form a structure in which the phosphine and olefin moieties occupy both axial and equatorial sites, which stands in contrast to a related bidentate olefin, phosphine ligand ("Lei" ligand), in which the olefins occupy the equatorial sites and phosphines the axial sites, exclusively. Copyright
CuI complexes containing a multidentate and conformationally flexible dibenzylidene acetone ligand (dbathiophos): Application in catalytic alkene cyclopropanation
Jarvis, Amanda G.,Whitwood, Adrian C.,Fairlamb, Ian J. S.
supporting information; experimental part, p. 3695 - 3702 (2011/07/30)
The synthesis and characterisation of a multidentate conformationally flexible ligand based on the dibenzylidene acetone core structure, dbathiophos (1), is described. Ligand 1 has a high affinity for cationic and neutral Cu I species. Three unique CuI complexes (4-6) are reported showing that the ligand backbone of dbathiophos is hemilabile, and able to adopt different 1,4-dien-3-one conformational geometries around CuI. Complexes 4 and 6 both effectively catalyse the cyclopropanation of styrene with ethyl diazoacetate at low catalyst loadings (1 mol% Cu). The Royal Society of Chemistry 2011.
An Efficient Synthesis of Dialkyl 2-Oxoalkanephosphonates and Diphenyl-2-oxoalkylphosphine Oxides from 1-Chloralkyl Ketones
Corbel, Bernard,Medinger, Luc,Haelters, Jean Pierre,Sturtz, Georges
, p. 1048 - 1051 (2007/10/02)
The synthesis of dialkyl 2-oxoalkanephosphonates and diphenyl-2-oxoalkylphosphine oxides, via an Arbuzov reaction of trialkyl phosphites or ethoxydiphenylphosphine with methoxycarbonylhydrazono derivatives of 1-chloroalkyl ketones followed by carbonyl deprotection, is described.
