Spectroscopic,anti-bacterial,anti-cancer and molecular docking of Pd(II) and Pt(II) complexes with (E)-4-((dimethylamino)methyl)-2-((4,5-dimethylthiazol-2-yl)diazenyl)phenol ligand

New ligand (E)-4-((dimethylamino)methyl)-2-((4,5-dimethylthiazol-2-yl)diazenyl)phenol (HDmazo) was prepared by the coupling reaction between 4,5-dimethylthiazol-2-amine and 4-((dimethylamino)methyl)phenol. Moreover, the [MCl₂(HDmazo)] and [M(HDmazo)₂] [M^II = Pd and Pt] were prepared using the direct reaction of equivalent molar of HDmazo and Na₂PdCl₄ or K₂PtCl₄. The HDmazo and its complexes were investigated by different spectroscopic techniques. In complexes (1–2) HDmazo ligand behaves as bidentate style through the nitrogen of azo group and nitrogen of thiazole ring towards Pd(II) and Pt(II). Or in a bidentate fashion via the oxygen atom of the hydroxylate group and nitrogen atom of azo group as mono-anion in complexes (3–4). Further, the study of biological activity against four pathogenic bacteria showed that compound (3) exhibited good activity compared to other compounds. Additional the anti-tumor action against A2870 cell lines was screened, and the complexes (1) and (2) displayed good activity with 7.45 ± 0.98 µM and 13.23 ± 1.43 µM, respectively. The binding mechanism of the prepared compounds with EGFR tyrosine kinase, was investigated using molecular docking experiments.     

Synthesis, characterization and spectroscopic properties of some new phenylazo-6-aminouracil

In this study, a series of new 5-phenylazo-6-aminouracil dyes were prepared by linking m-,p-nitroaniline, m-,p-chloroaniline, m-,p-anisidine, m-,p-toluidine, m-,p-cyanoaniline, p-ethoxyaniline, p-phenoxyaniline, p-ethylaniline, p-acetamidoaniline, p-acetylaniline, p-carboxyaniline and aniline to 6-aminouracil. The prepared dyes were characterized by UV-vis, FT-IR, ¹H NMR spectroscopic techniques and elemental analysis. The effect of acid and base upon the UV-vis spectra of these dyes were investigated. In addition, the solvatochromic behaviors and substituent effects in various solvents were evaluated.      

2-(p-取代苯乙烯基)噻唑碘盐的电子光谱研究

本文测定八种2-(p-取代苯乙烯基)噻唑碘盐染料的电子光谱。研究其吸收光谱的λ_(max)与取代基常数σ之间的定量关系,以λ_(max)值对Δσ(σρ-σm)作图呈线性趋势。并发现这些染料吸收带的溶剂效应符合 Nicol 理论。     

Utilization of DmbNHNH2 in the synthesis of amino-substituted 4-((3,5-diamino-1H-pyrazol-4-yl)diazenyl)phenols

(2,4-Dimethoxybenzyl)hydrazine (DmbNHNH₂) was utilized in the synthesis of Dmb-protected 4-((3,5-diamino-1H-pyrazol-4-yl)diazenyl)phenols. This unambiguous protection of the pyrazole endocyclic nitrogen atom enabled the preparation of amino-substituted 4-((3,5-diamino-1H-pyrazol-4yl)diazenyl)phenols that were inaccessible through direct substitution. The Boc group could be selectively cleaved in the presence of the Dmb group.     

溶剂效应和取代基效应对2-(2-氨基苯基)苯并噻唑光谱性质及激发态分子内质子转移的影响

合成了多种2-(2-氨基苯基)苯并噻唑(APBT)氨基氢原子被供电子及吸电子基团取代的衍生物, 并用紫外光谱﹑荧光光谱等方法和密度泛函理论(DFT)计算研究了溶剂效应和取代基效应对衍生物的光谱性质及激发态分子内质子转移(ESIPT)的影响规律. 结果表明, 相比于非极性溶剂环己烷, 随溶剂极性的增加及APBT-溶剂分子间氢键的形成, APBT的紫外-可见最大吸收峰和荧光最大发射峰均发生了一定程度的红移, 并对APBT的ESIPT产生了影响. 在APBT分子的氨基氮原子上引入不同的吸电子或斥电子取代基, 对氮原子的电荷性质有较大的影响. 在环己烷溶剂中, 甲基取代后的APBT仅有单重荧光发射峰, 体系未发生ESIPT过程; 而COCH₂Cl等吸电子基团能促进APBT的ESIPT, 其荧光发射光谱出现了明显的双重峰, 表明体系发生了激发态分子内质子转移反应. 量子化学的理论计算较好地验证了光谱实验结果.     

Synthesis and mesomorphic properties of n-butyl-4- [4-((4-n-alkoxyl-tetrafluorophenyl)ethynyl)benzyloxy]benzoates

A homologous series of n-butyl-4-[4-((4-n-alkoxyl-tetrafluorophenyl)ethynyl)benzyloxy]benzoates have been synthesized.Their phase transition temperatures have also measured by polarizing textural observation and confirmed by DSC.     

1-芳胺羰基-3-苄硫基-4-乙氧羰基(或氰基)-5-氨基吡唑的合成及生物活性

利用5-氨基-4-乙氧羰基(或氰基)-3-苄硫基吡唑与异氰酸酯的加成反应合成了一系列1-芳胺羰基-3-苄硫基-4-乙氧羰基(或氰基)-5-氨基吡唑。利用分子力学计算,解释了¹HNMR谱中的取代基效应。生物活性测定结果表明部分化合物具有良好的除草活性。     

Synthesis of Novel New 2-(2-(4-((3,4-Dihydro-4-oxo-3-aryl quinazolin-2-yl)methyl)piperazin-1-yl)acetoyloxy)-2-phenyl Acetic Acid Esters

Stereoselective diazotization of (S)-2-amino-2-phenyl acetic acid (L-phenyl glycine) (4) with NaNO₂ in 6% H₂SO₄ in a mixture of acetone and water gave optically pure (S)-2-hydroxy-2-phenyl acetic acid (L-mandelic acid) (5). Esterification, gave (S)-2-hydroxy-2-phenyl acetic acid esters (6). The latter was treated with chloroacetyl chloride in the presence of triethylamine (TEA) in dichloromethane (DCM) to yield (S)-2-chloroacetyloxy phenyl acetic acid ester (2). In another sequence, the reaction of 2-(chloromethyl)-3-arylquinazolin-4(3H)-one (9) treated with N-Boc piperazine, followed by deprotection of the Boc group, to obtain 3-aryl-2-((piperazin-1-yl)methyl) quinazolin-4(3H)-one (3). Reaction of 2 with 3 in the presence of K₂CO₃ and KI gave the title compound, 2-(2-(4-((3,4-dihydro-4-oxo-3-arylquinazolin-2-yl)methyl)piperazin-1-yl) acetoyloxy)-2-phenyl acetic acid esters (1). The structures of all the new compounds obtained in the present work are supported by spectral and analytical data.     

Synthesis of some 3-aryl-4-oxothiazolin-2-yl-[3-(2-aryl)indolyl]hydrazories

Several 4-aryl-l-[3-(2-aryl)indolyl]-3-thiosemiearbazones and 3-aryl-4-oxothiazolin-2-yl-[3-(2-aryl)indolyl] hydrazones were synthesized as possible antilertility agents. J. Heterocyclic Chem., 15 , 677 (1978)     

Synthesis and antimicrobial properties of new 2-((4-ethylphenoxy)methyl)benzoylthioureas

New acylthiourea derivatives, 2-((4-ethylphenoxy)methyl)-N-(phenylcarbamothioyl)benzamides, were tested by qualitative and quantitative methods on various bacterial and fungal strains and proved to be active at low concentrations against Gram-positive and Gram-negative bacteria as well as fungi. These compounds were prepared by the reaction of 2-((4-ethylphenoxy)methyl)benzoyl isothiocyanate with various primary aromatic amines, and were characterised by melting point and solubility. The structures were identified by elemental analysis, ¹H and ¹³C NMR, and IR spectral data. The level of antimicrobial activity of the new 2-((4-ethylphenoxy)methyl)benzoylthiourea derivatives was dependent on the type, number and position of the substituent on the phenyl group attached to thiourea nitrogen. The iodine and nitro substituents favoured the antimicrobial activity against the Gram-negative bacterial strains, while the highest inhibitory effect against Gram-positive and fungal strains was exhibited by compounds with electron-donating substituents such as the methyl and ethyl groups.     

Synthesis and mesomorphic properties of 4-n-alkoxy 4'-[4-((4-n-alkoxy-2,3,5,6-tetrafluoro-phenyl)ethynyl)benzyloxy]benzoates

Two series of tolane-based liquid crystals have been prepared that incorporate a tetrafluorophenyl moiety and a flexible methyl ether bond into the core structure. The mesomorphic properties have been studied by polarizing microscopic textural observation and DSC measurements. By comparison with their non-fluorinated analogues, the effect of tetrafluorophenylene on mesomorphic behaviour has been discussed in this paper.     

Synthesis and epimerization studies of 1-alkyl-2-carbomethoxy-(benzyloxy)-4-methylazetidines

A number of 1-alkyl-2-carbomethoxy(benzyloxy)-4-methylazetidines have been prepared by reaction of primary amines with α,γ-dibromo esters. Only one isomer was isolated from the reaction mixture. α-Aminolactones can also be obtained as the minor product of the reaction sequence.     

Electrochemical behavior and differential pulse voltammetric detection of thiobencarb on 2-(4-((4-ethoxyphenyl)diazenyl)phenylamino)ethanol-modified carbon paste electrode

Cyclic voltammetry, chronoamperometry, and rotating disk electrode voltammetry were used to investigate the electrochemical behavior of thiobencarb (TB) at carbon paste electrode modified with an azo dye, 2-(4-((4-ethoxyphenyl)diazenyl)phenylamino)ethanol (EDPE), EDPE/modified carbon paste electrode (MCPE). The modified electrode showed high electrocatalytic activity toward thiobencarb. The current was enhanced significantly relative to the situation prevailing when a bare glassy carbon electrode was used. The kinetics parameters of this process were calculated, the apparent electron transfer rate constant k _s and α (charge transfer coefficient between electrode and EDPE) were 14.6 s⁻¹ and 0.48, respectively. The experimental parameters were optimized, and the mechanism of the catalytic process was discussed. The best defined cathodic peak was obtained with 0.1 M acetate buffer (pH 3.0). The response of the sensor was very quick, and response time was approximately 5 s. The differential pulse voltammetry response of the MCPE was linear against the concentration of TB in the range of 0.96 to 106 μg L⁻¹. The limit of detection was found to be 0.025 μg L⁻¹. The precision was examined by carrying out eight replicate measurements at a concentration of 25 μg L⁻¹ TB; the relative standard deviation was 2.9%.     

Synthesis of (R)-2-(benzyloxy)-tetrahydro-5,5-dimethylfuran by a new oxidative rearrangement

The rearrangement under oxidative conditions of 3-(benzyloxy)-tetrahydro- 2,6,6-trimethyl-2H-pyran-2-carbaldehydes to afford a chiral protected tetrahydrofuran lactol is described.     

Studies on the solvatochromism of Fe(CN)2(phen)2

Summary The influence of organic solvents on the electronic spectra of Fe(CN)₂(phen)₂ has been investigated by trichromatic colorimetry. The color parameters of these solutions have been calculated on the basis of the absorption spectra and are described in the CIE and CIELAB color spaces. It has been shown that one of the parameters (the so-called hue angle) could be related to some acidity parameters of solvents. Thus, it is possible to calculate the hue angle and, therefore, to predict the color of solution if the solvent acceptor number is known, or vice versa.

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Untersuchung zur Solvatochromie von Fe(CN)₂(phen)₂

Zusammenfassung Der Einfluß organischer Lösungsmittel auf die UV-Spektren von Fe(CN)₂-(phen)₂ wurde mittels trichromatischer Kolorimetrie untersucht. Die Farbparameter der Lösungen wurden aus den Absorptionsspektren berechnet und werden in den CIE- und CIELAB-Farbräumen beschrieben. Es konnte gezeigt werden, daß einer der Farbparameter (der sogenannte Farbtonwinkel) zu den Aciditätsparametern des jeweiligen Lösungsmittels in Beziehung gesetzt werden kann. Es ist daher z.B. möglich, die Farbe der Lösung vorherzusagen, wenn die Akzeptorzahl des Lösungsmittels bekannt ist und umgekehrt.

     

1-苯基-3-(3'-吲哚基)-5-取代苯基-2-吡唑啉的合成及1H NMR和MS中的取代基效应

J-(3'-吲哚基)-3-取代苯基-2-丙烯-1-酮与茉肼反应,合成了10种新的1-苯基-3-(3'-吲哚基)-5-取代苯基-2-吡唑啉衍生物,其结构通过各种波谱证实.讨论了此系列化合物¹HNMR和Ms中的取代基效应,得出取代基常数σ或σ⁺与质子化学位移,碎片相对丰度之间存在着良好的线性关系.     

The effect of solvent on the reactions of allyltin (IV) compounds with singlet oxygen, 4-phenyl-1,2,4-triazoline-3,5-dione and diethyl azodicarboxylate

The effect of the influence on the increase of polarity of the solvent on the selectivity and rate of metalloene reactions of different allyltin compounds with singlet oxygen, 4-phenyl-1,2,4-triazoline-3,5-dione (TD) and diethyl azodicarboxylate has been studied.     

Synthesis of diverse (E)-2-((1H-imidazol-1-yl)methyl)-2-((benzyloxy)methyl)-2,3-dihydro-1H-inden-1-one O-benzyl oxime derivatives as potent antileishmanial agents

A series of (E)-2-((1H-imidazol-1-yl)methyl)-2-((benzyloxy)methyl)-2,3-dihydro-1H-inden-1-one O-benzyl oximes ( 6a-j ) were prepared and evaluated for their in vitro antileishmanial potency against Leishmania donovani (in promastigote and amastigote models). At a concentration of 05-μg/mL, compounds 3a-d , 4a-d , 5a , 5b , 6a-d, and 7a-d exhibited 97% to 100% and 87% to 100% inhibition against promastigotes and amastigotes, respectively. Compounds 6a , 6d-6j and 6a , 6i , 6j exhibited equal antileishmanial potency to that of SSG and Pentamidin at lower values of IC₅₀.