635-84-7Relevant academic research and scientific papers
Synthesis, characterization, theoretical calculations and biochemical evaluation of a novel oxime ligand with complexes
G?rgülü, Güven?,Dede, Bülent
, p. 473 - 491 (2019)
A novel amine containing ketooxime ligand (HBOX) and its Cu(II) and Mn(II) complexes were synthesized, characterized and tested for some of their biological activities. Structural characterization was carried out by elemental analysis, ICP-OES, 1H and 13C NMR, UV–Vis, FT-IR, XRD, TG-DTG, magnetic susceptibility and molar conductivity measurements. Elemental analyses, stoichiometric and spectroscopic data of the metal complexes indicated that the metal:ligand ratio was found to be 1:2 and the metal ions were coordinated to the oxime oxygen and amine nitrogen atoms. Furthermore, DFT/B3LYP method with 6-311G(d,p) and LANL2DZ basis sets were used for full optimization of molecular geometries of the ligand and complexes, respectively. The vibrational frequencies, isotropic chemical shifts (1H and 13C NMR), electronic transition absorption wavelengths, HOMO and LUMO analyses and molecular electrostatic potential (MEP) properties of the synthesized molecules have been calculated. The results obtained experimentally were confirmed by the theoretical data which are in good agreement. Inhibitory capacity of the HBOX was investigated against neoangiogenic factors, vascular endothelial growth factor receptor-2 (VEGFR-2) and cyclooxygenase-2 (COX-2) by molecular docking studies. HBOX bound to COX-2 protein with 2 hydrogen bonds at the lowest energy level which indicates the most stabilized form of the protein ligand complex. Complexes were also tested for their catecholase and phenoxazinone synthase-like activities using spectrophotometric procedures. Catecholase and phenoxazinone synthase-like enzyme activities were spectrophotometrically followed by the increase in absorbance at 400 and 433 nm resulted from the oxidation reaction of 3,5-di-tert-butylcatechol and 2-aminophenol to 3,5-di-tert-butylquinone and 2-aminophenoxazine-3-one, respectively. According to the calculated kobs values, the Mn(II) complex was found to be more active for both enzymes compared to Cu(II).
Synthesis, characterization, DFT calculations and catalase-like enzymatic activities of novel hexadentate Schiff base and its manganese complexes
Karako?, Murat,Dede, Bülent,Erdem-Tun?men, Mukadder,Karipcin, Fatma
, p. 250 - 262 (2019)
We reported the synthesis of the manganese(II) and manganese(III) complexes of a novel hexadentate Schiff base ligand (HBME) (1) obtained from the condensation of triethylenetetramine and 2 equiv. of 1-(biphenyl)-2-hydroxyimino-2-(morpholino)-1-ethanone.
Poloxamer P85 increases anticancer activity of Schiff base against prostate cancer in vitro and in vivo
Demircia, Selami,Dogana, Aysegül,Türkmend, Nese Basak,Telcia, Dilek,?aglayanc, Ahmet B.,Bekerc, Mustafa ?.,Kili?c, Ertugrul,?zkanb, Ferda,Dedee, Bülent,Sahina, Fikrettin
, p. 869 - 879 (2017)
Prostate cancer is the second most common cancer among men and the leading cause of death after lung cancer. Development of hormone-refractory disease is a crucial step for prostate cancer progression for which an effective treatment option is currently unavailable. Therefore, there is a need for new agents that can efficiently target cancer cells, decrease tumor growth, and thereby extend the survival of patients in late-stage castration-resistant prostate cancer. In the current study, a novel heterodinuclear copper(II)Mn(II) Schiff base complex combined with P85 was used to evaluate anticancer activity against prostate cancer in vitro and in vivo. Cell proliferation and cytotoxicity were evaluated by cell viability, gene, and protein expression assays in vitro. Results showed that the heterodinuclear copper(II)Mn(II) complex-P85 combination decreased cell proliferation by upregulating the apoptotic gene expressions and blocking the cell proliferation-related pathways. Tramp-C1-injected C57/B16 mice were used to mimic a prostate cancer model. Treatment combination of Schiff base complex and P85 significantly enhanced the cellular uptake of chemicals (by blocking the drug transporters and increased life time), suppressed tumor growth, and decreased tumor volume steadily over the course of the experiments. Overall, heterodinuclear copper(II)Mn(II) complex-P85 showed remarkable anticancer activity against prostate cancer in in vitro and in vivo.
NOVEL 5-[4-(2-BIPHENYL-4-YL-2-OXO-ETHOXY)-BENZYLIDENE]-THIAZOLIDINE-2,4-DIONES, THEIR SYNTHESIS AND USES THEREOF
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Page/Page column 21, (2019/02/06)
Disclosed are novel 5-[4-(2-biphenyl-4-yl-2-oxo-ethoxy)-benzylidene]-thiazolidine-2,4-dione compounds of general formula (I), their pharmaceutically acceptable salts, solvates their synthesis and uses thereof, to pharmaceutical compositions containing compounds and to the use of such compounds and composition in medicines either alone or in combination with other compounds.
Micro-electro-flow reactor (μ-EFR) system for ultra-fast arene synthesis and manufacture of daclatasvir
Mahajan, Bhushan,Mujawar, Taufiqueahmed,Ghosh, Subhash,Pabbaraja, Srihari,Singh, Ajay K.
, p. 11852 - 11855 (2019/10/11)
The World Health Organization (WHO) has listed daclatasvir (DCV), symmetrical arene, as one of the essential medicines for human health. DCV manufacturing is usually carried out in a non-continuous or "batch" approach over multiple locations and is severely limited by long production times (3-10 days), resulting in non-affordability (highly expensive) and disruption of the potential chain supply. Here, we report the total process system including the development of a novel electro-flow reactor containing patterned electrodeposited Ni or Pt nanoparticles over a copper electrode for a C-C coupling reaction in a co-reductant/oxidant-free, ultra-fast process for symmetrical substituted/unsubstituted biphenyl synthesis. This method was further extended to a new generation commercial batch synthetic route for continuous flow ultra-fast daclatasvir synthesis in 33.2 min. We envisage that this micro-electro-flow reactor (μ-EFR) system platform will substantially enable advances in continuous-μ-flow fine chemical manufacturing, multistep reaction sequences, reaction devising equipment, and real-time extraction.
Photochemical reactions of halogenated aromatic 1,3-diketones in solution studied by steady state, one- and two-color laser flash photolyses
Yamaji, Minoru,Suwa, Yurie,Shimokawa, Rieko,Paris, Cecilia,Miranda, Miguel ángel
, p. 1673 - 1684 (2015/09/07)
Photochemical processes of 4-tert-butyl-4′-methoxydibenzoylmethane (Avobenzone, AB), 4-phenylbenzoylbenzoyl-, 4-phenylbenzoyl-2′-furanyl- and 4-phenylbenzoyl-2′-thenoylmethanes (PB@Ph, PB@F and PB@T, respectively) substituted with Br and Cl at the C2 position were studied by stationary and laser flash photolyses in solution. The absorption spectral features showed that the molecular structures of the halogenated diketones are in the keto forms while those of halogen-free diketones are in the enol forms. The excited singlet and triplet state energies were determined from the absorption and emission spectra. From the absorption spectral changes upon steady state photolysis of brominated diketones in ethanol, the corresponding halogen-free diketones were formed due to Br elimination being the major photochemical process. The determined quantum yields for the formation of the halogen-free diketones were independent of the amount of dissolved oxygen, indicating that the elimination process is an event in the excited singlet (S1) states. In contrast, from the observed absorption spectra obtained upon photolysis of chlorinated AB and PB@Ph, it was inferred that Norrish type I is the major photochemical reaction in the S1 states in acetonitrile. Chlorinated PB@F and PB@T were found to undergo Cl elimination in the S1 states in cyclohexane to form the corresponding halogen-free diketones. Laser photolysis studies of brominated AB in acetonitrile and ethanol provided a transient absorption spectrum ascribable to the Avobenzone radical (ABR) produced by debromination as the initial intermediate, followed by the AB formation in ethanol. The quenching rate constant of ABR by ethanol and the quantum yield of the AB formation via ABR were determined. These observations provided evidence that H-atom abstraction of ABR from ethanol is responsible for the AB formation. Conversely, laser flash photolysis of brominated and chlorinated PB@Ph, PB@F and PB@T demonstrated the formation of the triplet-triplet absorption spectra. No chemical reactions were found to occur in the triplet (T1) states. Two-color two-laser photolysis studies were carried out on the T1 state of chlorinated PB@Ph, PB@F and PB@T, resulting in the formation of the corresponding halogen-free diketones. These observations confirmed the occurrence of Cl elimination in the highly excited triplet (Tn, n ≥ 2) states. Based on the computed bond dissociation energies for the C-halogen and C-C bonds, switching mechanisms of dehalogenation and α-cleavage were discussed.
Design, synthesis, pharmacological evaluation and computational studies of 1-(biphenyl-4-yl)-2-[4-(substituted phenyl)-piperazin-1-yl]ethanones as potential antipsychotics
Bhosale, Sharad H.,Kanhed, Ashish M.,Dash, Radha Charan,Suryawanshi, Mugdha R.,Mahadik
, p. 358 - 365 (2014/02/14)
This article describes the design of biphenyl moiety linked with aryl piperazine and syntheses of fourteen 1-(biphenyl-4-yl)-2-[4-(substituted phenyl)-piperazin-1-yl]ethanone derivatives along with their pharmacological evaluation for antipsychotic activity and computational studies including quantitative structure activity relationship (QSAR) and descriptor based similarity study. All compounds were found to exhibit considerable anti-dopaminergic and anti-serotonergic activity in behavioural models. Among all derivatives, compound 1-(biphenyl-4-yl)-2-[4-(2-methoxyphenyl)-piperazin-1- yl]ethanone (3c) and 1-(biphenyl-4-yl)-2-[4-(2,3-dichlorophenyl)-piperazin-1-yl] ethanone (3k) showed impressive antipsychotic profile with lower potency for catalepsy induction. These results were found to be sturdily matching with docking study in designing of compounds with homology model of human dopamine D2 receptor. Also the QSAR study strongly supports the obtained results.
N-BIPHENYLACYL THIAZOLIDINE-2,4-DIONE DERIVATIVES, THEIR SYNTHESIS AND USES
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Page/Page column 30-31, (2010/08/08)
N- Biphenylacyl-thiazolidine-2,4-dione derivatives of the general formula (I); where in, Z1 and Z2 represent H, or together forms a chemical bond; R1 represents H, alkoxy, nitro, halo, hydroxy, optionally substituted amino group, - O- (CH2)n-N(R7)(R8), -O-(CH2)n-R9, wherein n is 0 to 5, -COOH, -CN, linear or branched alkyl, substituted alkyl, cycloalkyl, -S- R11 alkyl thio, acyl, aroyl, substituted or unsubstituted heterocyclic, alkoxy carbonyl, aryloxy, aryloxy carbonyl; R2 represents H, halo, hydroxy, linear or branched alkyl, substituted alkyl; R3, R4, R5 independently represents H, alkoxy, hydroxy, linear or branched alkyl, substituted alkyl; R6 represents H, -COOH, linear or branched alkyl, -CN, -SO3H, optionally substituted amino group; R7 represents H, linear or branched alkyl, cyclo alkyl, acyl, aroyl, aralkyl where in aryl moiety is substituted or unsubstituted, or an aryl; R8 represents a substituted or unsubstituted heterocyclic, linear or branched alkyl, substituted alkyl; R9 represents a substituted or unsubstituted heterocyclic, substituted or unsubstituted aromatic, substituted or unsubstituted cycloalkyl, fused aryl-heterocyclyl; when R1 represents alkoxy group, and Z1 and Z2 together forms a chemical bond then, R2 or R3 or R4 or R5 is other than H, and when R1, R2, R3, R4, R5 are each independently represents H, and Z1 and Z2 together forms a chemical bond then R6 is not H; And when R1, R2, R3, R4, R5 represents independently or together halo group and - Z1 and Z2 together forms a chemical bond, then R6 is not H; are novel compounds, their isomers and their enantiomers and their pharmaceutically acceptable salts or solvates and their pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicines and process for preparing the same.
Synthesis of (2-hydroxo-5-chlorophenylaminoisonitrosoacetyl)phenyl ligands and their complexes: Spectral, thermal and solvent-extraction studies
Karipcin, Fatma,Dede, Bülent,Cengiz, Mustafa
experimental part, p. 530 - 540 (2010/08/04)
Four different types of new ligands Ar[COC(NOH)R] n (Ar=biphenyl, n = 1 H2L1; Ar=biphenyl, n = 2 H 4L2; Ar=diphenylmethane, n = 1 H2L3; Ar=diphenylmethane, n = 2 H4L4; R=2-amino-4-chlorophenol in all ligands) have been obtained from 1 equivalent of chloroketooximes Ar[COC(NOH)Cl] n (HL1-H2L4) and 1 equivalent of 2-amino-4-chlorophenol (for H2L1 and H 2L3) or 2 equivalent of 2-amino-4-chlorophenol (for H 4L2 and H4L4). (Mononuclear or binuclear cobalt(II), nickel(II), copper(II) and zinc(II) complexes were synthesized with these ligands.) These compounds have been characterized by elemental analyses, AAS, infra-red spectra and magnetic susceptibility measurements. The ligands have been further characterized by 1H NMR. The results suggest that the dinuclear complexes of H2L1 and H2L3 have a metal:ligand ratio of 1:2; the mononuclear complexes of H4L2 and H4L4 have a metal:ligand ratio of 1:1 and dinuclear complexes H4L2 and H4L4 have a metal:ligand ratio of 2:1. The binding properties of the ligands towards selected transition metal ions (Mn II, CoII, NiII, CuII, Zn II, PbII, CdII, HgII) have been established by extraction experiments. The ligands show strong binding ability towards mercury(II) ion. In addition, the thermal decomposition of some complexes is studied in nitrogen atmosphere.
Synthesis and characterization of some Borylated (4-Biphenyl)(N-arylamino) glyoxime complexes
Karipcin,Erdem-Tuncmen,Baskale-Akdogan,Dede
body text, p. 525 - 535 (2010/02/28)
A series of Cu(II), Ni(II) and Co(III) complexes of the type [M(L n)2(H2O)2(BF2) 2] and [Co(Ln)2PyCl(BF2) 2] (where M = Cu(II) or Ni(II); n = 1,2; L = bidentate dioxime ligands) have been synthesized by the reactions of dioxime complexes with boron trifluoride diethyl ether complex in acetonitrile under nitrogen atmosphere. In all these reactions, the bridging protons of the dioxime complexes replace BF2 groups. These complexes have been characterized by elemental analyses, FT-IR, ICP-OES, 1H NMR together with magnetic susceptibility measurements. In particular, the thermal decomposition of all the complexes was studied in nitrogen atmosphere.
