15191-68-1Relevant academic research and scientific papers
Synthesis, characterization and cell viability test of six vanadyl complexes with acetylacetonate derivatives
Sgarbossa, Speranza,Diana, Eliano,Marabello, Domenica,Deagostino, Annamaria,Cadamuro, Silvano,Barge, Alessandro,Laurenti, Enzo,Gallicchio, Margherita,Boscaro, Valentina,Ghibaudi, Elena
, p. 26 - 37 (2013)
Vanadium compounds are known to display a number of therapeutic effects, namely insulin-mimetic and cardiovascular effects. Evidence of the antiproliferative and proapoptotic activity of a number of vanadyl complexes, together with their low toxicity, establishes these metal compounds as promising antitumoral therapeutic agents. In the present work, we describe the synthesis and full characterization of six new vanadyl complexes with acetylacetonate derivatives bearing asymmetric substitutions on the β-dicarbonyl moiety: the complexes were characterized in the solid state as well as in solution. Our results show that all complexes are in square pyramidal geometry; cis isomers in the equatorial plane are favored in the presence of strongly coordinating solvents. EPR evidence suggests that all complexes are in the bis-chelate form, although in two cases the mono-chelated complex seems to be present as well. Preliminary tests carried out on non-tumor and tumor cell lines show that these complexes are effective in suppressing cell viability and elicit a distinct response of tumor and non-tumor cells.
A convenient and regioselective synthesis of 4-trifluoromethylpyridines
Katsuyama,Ogawa,Yamaguchi,Funabiki,Matsui,Muramatsu,Shibata
, p. 1321 - 1324 (1997)
Trifluoromethyl-substituted β-diketones regioselectively react with primary enamines such as β-aminocrotononitrile and ethyl β-aminocrotonate, providing moderate to good yields of 4-trifluoromethylpyridines.
Synthesis and photoluminescent properties of Eu (III) complexes with fluorinated β-diketone and nitrogen heterocyclic ligands
Wang, Dan,Luo, Zheng,Liu, Zhao,Wang, Dunjia,Fan, Ling,Yin, Guodong
, p. 398 - 404 (2016)
Two fluorinated β-diketones and their six europium (III) complexes using 2,2-dipyridine, 1,10-phenanthroline or 4′-phenyl-terpyridine as the secondary ligand were synthesized and characterized. The photoluminescence behavior for these complexes was investigated in solid state in detail. Based on the emission spectra and luminescence decay curves of these complexes in solid state, the Judd-Ofelt intensity parameters (Ωt), lifetime (τ) and luminescence quantum efficiency (η) were determined. The Ω2 values indicate that the europium (III) ion is in a highly polarizable chemical environment in these complexes. Europium (III) complexes with the secondary ligands 2,2-dipyridine or 1,10-phenanthroline exhibited much better photoluminescence properties than complexes with the secondary ligand 4′-phenyl-terpyridine. Especially, europium (III) complexes of 4,4,4-trifluoro-1-(4-fluorophenyl)-butane-1,3-dione containing the secondary ligands 2,2-dipyridine or 1,10-phenanthroline showed a longer lifetime (τ = 0.799 and 0.826 ms, respectively) and a higher luminescence quantum efficiency (η = 56.5 and 56.1, respectively) among these complexes.
Reaction of aroyl- and hetaroyltrifluoroacetones with acylhydrazines: Regioselectivity and tautomerism of the condensation products
Pakal'nis,Zerova,Yakimovich
, p. 1732 - 1741 (2007)
Acylhydrazines react with 1,3-diketones of the general formula CF 3COCH2COR (where R is an aryl or hetaryl group) at both carbonyl groups. The reaction at the trifluoroacetyl group is favored by donor substituents in the aromatic ring of the 1,3-diketone or by the 2-furyl and, especially, 2-thienyl group as a hetaryl substituent, as well as by elevated temperature. The condensation products at the carbonyl group contiguous to the aryl or hetaryl ring have the structure of 5-hydroxy-4,5-dihydropyrazoles and do not undergo tautomeric transformations in solution. The condensation products at the trifluoroacetyl group have either 5-hydroxy-4,5-dihydropyrazole or hydrazone structure and give rise to ring-chain tautomeric equilibrium in solution. Electron-withdrawing substituents in the aromatic ring of the 1,3-dicarbonyl fragment and CDCl3 as solvent favor formation of the cyclic tautomer. The state of the tautomeric equilibrium is weakly sensitive to structural variations in the hydrazine component.
Development of celecoxib-derived antifungals for crop protection
Liu, Xiuxiu,Ma, Yihui,Sun, Xianglong,Yang, Jun,Yang, Lirong
, (2020/02/27)
Selective COX-2 inhibitor celecoxib was found directly inhibiting the growth of tested phytopathogenic fungi with the inhibitory rate ranging from 30 to 40% at 100 μg/ml. Lead optimization of celecoxib led to the identification of compound 12 among its derivatives as the most active antifungal candidate. The antifungal effect of compound 12 was supposed to be independent of COX-2 inhibition. Transcriptome profiling analysis of Fusarium graminearium (PH-1) treated with compound 12 brought about 406 up-regulated and 572 down-regulated differentially express genes (DEGs) respectively.
An Integrated Continuous Flow Micro-Total Ultrafast Process System (μ-TUFPS) for the Synthesis of Celecoxib and Other Cyclooxygenase Inhibitors
Sthalam, Vinay Kumar,Singh, Ajay K.,Pabbaraja, Srihari
supporting information, p. 1892 - 1899 (2019/10/11)
Integrated continuous manufacturing has emerged as a promising device for the rapid manufacturing of active pharmaceutical ingredients (APIs). We herein report a newly designed continuous flow micro-total process system platform for the rapid manufacturing of celecoxib, a selective nonsteroidal anti-inflammatory drug. This approach has been proven generally for the synthesis of several alkyl and aryl substituted pyrazoles. In order to minimize the tedious work-up process of potential reaction intermediates/products, we have developed a continuous flow extraction and separation platform to carry out the entire reaction sequence resulting in a short residence time with good yield. The present process was further extended to gram-scale synthesis of the COX-2-related API, viz. celecoxib, in the continuous flow process.
Application of 1,5-diaryl-3-pyrazole compound in prevention and control of agricultural fungal diseases
-
Paragraph 0020, (2018/12/13)
The invention belongs to the technical field of pesticides, and particularly relates to application of 1,5-diaryl-3-pyrazole compound in prevention and control of agricultural fungal diseases. The general structural formula of the 1,5-diaryl-3-pyrazole compound is as shown in the description, wherein R1 is selected from fluorine, methoxyl or methyl; and R2 is selected from -CHOOH, -SO2NH2, -NO2, -F,-C1 or -Br. Compared with a traditional agricultural fungicide, the 1,5-diaryl-3-pyrazole compound provided by the invention is unique in structure, adopts an action mechanism different from that ofa traditional fungicide, and has no cross resistance risks on resistance strains generated by an existing fungicide.
Design and synthesis of novel benzenesulfonamide containing 1,2,3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors
Kumar, Rajiv,Vats, Lalit,Bua, Silvia,Supuran, Claudiu T.,Sharma, Pawan K.
, p. 545 - 551 (2018/06/18)
In a quest to discover new biologically active compounds, a series of twenty novel heterocyclic derivatives substituted at position 5 with -H (7a-7j) or -CF3 (8a-8j), bearing benzenesulfonamide at N-1 position and various aroyl groups at position 4 of the 1,2,3-triazole ring was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibition potential against four human (h) isoforms hCA I, II, IV and IX. All the compounds (7a-7j and 8a-8j) were synthesized via [3+2] cycloaddition reaction from 4-azidobenzenesulfonamide. Interestingly, compounds 7a-7j were prepared in one pot manner via enaminone intermediate using novel methodology. All the newly synthesized compounds (7a-7j & 8a-8j) were found to be excellent inhibitors of edema related isoform hCA I with their inhibition constant (Ki) ranging from 30.1 to 86.8 nM as compared to standard drug acetazolamide (AAZ) with Ki = 250 nM. Further it was found that most of tested compounds were weaker inhibitors of isoform, hCA II although compounds 7b, 7d-7e, 8a, 8d-8f, 8i (mostly with electron withdrawing substituents) have shown better inhibition potential (Ki i = 52.4 nM) than AAZ (Ki = 74 nM) while against tumor associated hCA IX, all the compounds have shown moderate inhibition potential. Present study have added one more step in exploring the 1,2,3-triazlole moiety in the medicinal field.
An SAR study of hydroxy-trifluoromethylpyrazolines as inhibitors of Orai1-mediated store operated Ca2+ entry in MDA-MB-231 breast cancer cells using a convenient Fluorescence Imaging Plate Reader assay
Stevenson, Ralph J.,Azimi, Iman,Flanagan, Jack U.,Inserra, Marco,Vetter, Irina,Monteith, Gregory R.,Denny, William A.
, p. 3406 - 3413 (2018/05/24)
The proteins Orai1 and STIM1 control store-operated Ca2+ entry (SOCE) into cells. SOCE is important for migration, invasion and metastasis of MDA-MB-231 human triple negative breast cancer (TNBC) cells and has been proposed as a target for cancer drug discovery. Two hit compounds from a medium throughput screen, displayed encouraging inhibition of SOCE in MDA-MB-231 cells, as measured by a Fluorescence Imaging Plate Reader (FLIPR) Ca2+ assay. Following NMR spectroscopic analysis of these hits and reassignment of their structures as 5-hydroxy-5-trifluoromethylpyrazolines, a series of analogues was prepared via thermal condensation reactions between substituted acylhydrazones and trifluoromethyl 1,3-dicarbonyl arenes. Structure-activity relationship (SAR) studies showed that small lipophilic substituents at the 2- and 3-positions of the RHS and 2-, 3- and 4-postions of the LHS terminal benzene rings improved activity, resulting in a novel class of potent and selective inhibitors of SOCE.
A Sequential Route to Cyclopentenes from 1,6-Enynes and Diazo Ketones through Gold and Rhodium Catalysis
Kale, Balaji S.,Lee, Hsin-Fu,Liu, Rai-Shung
supporting information, p. 402 - 409 (2017/02/10)
This work reports the construction of cyclopentene cores from 1,6-enynes and aryl diazo ketones through two new reaction sequences involving initial gold-catalyzed cyclization of 1,6-enynes with diazo species, followed by rhodium-catalyzed skeletal rearrangement of the resulting 3-cyclopropyl-2-en-1-ones. In most instances the rhodium-catalyzed reactions afforded cyclopentene derivatives whereas several n-alkyl- or ortho-substituted phenyl ketones delivered seven-membered oxacycles. A plausible mechanism provides rationales for these two distinct products. (Figure presented.).
