Fluorescence properties of three potential antitumoral compounds, a 3-(dibenzothien-4-yl)indole 1, a phenylbenzothienoindole 2 and a 3-(dibenzofur-4-yl)indole 3, were studied in solution and in lipid aggregates of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanolamine
(DOPE) and egg yolk phosphatidylcholine (Egg-PC). The 3-(dibenzofur-4-yl)indole 3 exhibits the higher fluorescence quantum yields in all solvents studied (0.32 ≤ ΦF ≤ 0.51). All the compounds present a solvent sensitive emission, with significant red shifts in alcohols. The results point
to an ICT character of the excited state, more pronounced for compound 1. Fluorescence (steady-state) anisotropy measurements of the compounds incorporated in lipid aggregates of DPPC, DOPE and
Egg-PC indicate that the three compounds are deeply located in the lipid bilayer, feeling the difference between the rigid
gel phase and fluid phases. 相似文献
The electronic absorption, fluorescence excitation and emission spectra, and fluorescence quantum yields of novel fused thienobenzofurans,
including thieno[3,2-b][1]benzofuran (1), [1]benzothieno[3,2-b]furan (2), and [1]benzothieno[3,2-b][1]benzofuran (3), were recorded in fourteen solvents of different polarities at room temperature. Compound 2 was not fluorescent. Experimental ground-state dipole moments of compounds 1–3 were measured in benzene at 298 K and compared with the corresponding theoretical dipole moment values. The solvent effects
on the electronic absorption and fluorescence spectra of these thienobenzofurans were quantitatively investigated by means
of solvatochromic correlations based on the Kawski-Chamma-Viallet and McRae equations. A weak negative solvatochromic behavior
was found for these compounds, showing that their dipole moments are slightly lower in the excited singlet-state than in the
ground-state. Kamlet-Abboud-Taft multiparameter relationships were also established for electronic absorption and fluorescence
wavenumbers, and fluorescence quantum yields in most solvents, demonstrating the occurrence of specific solute-solvent interactions. 相似文献
Pyrazolo[3,4-b]pyridines having 4-chloro-5-chloroethyl side chain are synthesized by the reaction of 5-aminopyrazole and cyclic β-formylester
gave aminopyrazolodihydrofuranone intermediate, which on cyclization in phosphorous oxychloride exclusively converted in to
4-chloro-5-chloroethyl pyrazolo[3,4-b]pyridines 4(a-b) in major amount. The side chain with acetic acid, thiourea and aromatic amines are used to form angular ring leads to formation
of tricyclic Furo[2,3-d]pyrazolo[2,3-b]pyridines 5(a-b), pyrazolo[3,4-b]thieno[2,3-d]pyridines 6(a-b) and pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines 7(a-n) respectively. The substituents effect at C4 position on fluorescence properties of pyrazolopyridines has been studied. Moreover the effect of electron donor and halogen
substituents on fluorescence properties of pyrazolopyrrolopyridines 7(a-n) has been investigated along with their fluorescent quantum yield. 相似文献
A practical strategy was developed for the preparation of highly substituted 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones from 4,6-dichloro-5-formylpyrimidine, primary amines, and aldehydes. The key step for this synthesis entails a cyclization
reaction involving an intramolecular amide addition to an iminium intermediate formed in situ from 4-amino-pyrimidine-5-carboxamide
2 and aldehydes to form the pyrimido[4,5-d]pyrimidine core with a strategically placed 5-Cl group for further derivatization. The utility of this methodology was demonstrated
through the preparation of a 27-membered library of representative 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones in moderate to good yields. 相似文献
An efficient and facile green synthesis of spirooxindole derivatives bearing pyrano[2,3-c]pyrazole moiety has been achieved via a \(\mathrm{CeO}_{2}\)-NPs catalyzed four-component reaction in water. The protocol offers an environmentally benign and effective approach to highly functionalized and biologically interesting spiro[indoline-3,4\(^\prime \)-pyrano[2,3-c]pyrazole] derivatives. The synthesized compounds exhibit potent antioxidant and antibacterial activities. 相似文献
A new series of quinolotacrine hybrids including cyclopenta- and cyclohexa-quinolotacrine derivatives were designed, synthesized, and assessed as anti-cholinesterase (ChE) agents. The designed derivatives indicated higher inhibitory effect on the acetylcholinesterase (AChE) with IC50 values of 0.285–100 µM compared to butyrylcholinesterase (BChE) with IC50 values of?>?100 µM. Of these compounds, cyclohexa-quinolotacrine hybrids displayed a little better anti-AChE activity than cyclopenta-quinolotacrine hybrids. Compound 8-amino-7-(3-hydroxyphenyl)-5,7,9,10,11,12-hexahydro-6H-pyrano[2,3-b:5,6-c'] diquinolin-6-one (6m) including 3-hydroxyphenyl and cyclohexane ring moieties exhibited the best AChE inhibitory activity with IC50 value of 0.285 µM. The kinetic and molecular docking studies indicated that compound 6m occupied both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of AChE as a mixed inhibitor. Using neuroprotective assay against H2O2-induced cell death in PC12 cells, the compound 6h illustrated significant protection among the assessed compounds. In silico ADME studies estimated good drug-likeness for the designed compounds. As a result, these quinolotacrine hybrids can be very encouraging AChE inhibitors to treat Alzheimer’s disease.
Graphic abstract
A novel series of quinolotacrine hybrids were designed, synthesized, and evaluated against AChE and BChE enzymes as potential agents for the treatment of AD. The hybrids showed good to significant inhibitory activity against AChE (0.285–100 μM) compared to butyrylcholinesterase (BChE) with IC50 values of?>?100 μM. Among them, compound 8-amino-7-(3-hydroxyphenyl)-5,7,9,10,11,12-hexahydro-6H-pyrano[2,3-b:5,6-c′] diquinolin-6-one (6 m) bearing 3-hydroxyphenyl moiety and cyclohexane ring exhibited the highest anti-AChE activity with IC50 value of 0.285 μM. The kinetic and molecular docking studies illustrated that compound 6 m is a mixed inhibitor and binds to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of AChE.
Summary The phosphorus ylide obtained from the reaction between 2-aminobenzo[d]isothiazol-3-one and dimethyl acetylenedicarboxylate in the presence of triphenylphosphine undergoes a smooth intramolecular
Wittig-type reaction to produce, in a one-pot reaction, 3-H-benzo[d]pyrazolo[1,5-b]isothiazole-2,3a-dicarboxylic acid dimethyl ester, a novel functionalized heterocyclic compound. 相似文献
A facile method for the synthesis of substituted pyrrolo[2,3-c]pyridine-7-ones is developed that applies an acid-promoted intramolecular cyclization of 2-pyrrolecarboxylic acid amidoacetals as key step. The synthesis is easily scaled up to 1.5?mol quantity with no yield decrease. The alkylation/arylation reaction of the pyrrolo[2,3-c]pyridine-7-ones proceeds regioselectively giving N6-substituted derivatives. 相似文献
The utilization of an ionic liquid, [bmim][BF4] as both reaction medium and promoter for a multi-component reaction of aldehyde (1) and 5-amino-3-methyl-1-phenylpyrazole (2) with Meldrum acid (3) or dimedone (5) is studied. From this reaction, pyrazolo[3,4-b]pyridinone (4) and pyrazolo[3,4-b]quinolinone (6) derivatives were prepared in high yields. This novel procedure showed such advantages as environmentally benign nature,
enhanced efficiency, simple operation process, and mild reaction conditions. As an application, the procedure was successfully
used in the preparation of a set of pyrimidine nucleoside–pyrazolo[3,4-b]pyridine and pyrazolo[3,4-b]quinolinone hybrids with potential biological activities. 相似文献
A large library of diversified compounds (pyrano [2,3-d]pyrimidines, pyrido[2,3-d] pyrimidines and a variety of spirooxindoles) were synthesized through a very efficient, economical and environmentally benign
process utilizing magnetic nanoparticles. Ease of recovery using an external magnetic field is an additional ecofriendly attribute
of this catalytic system. Most of the compounds are new; therefore, could be further explored for their pharmaceutical application.
Moreover, column chromatography and recrystallisation of the products is not required as the crude products are already highly
pure and hence can be used for target oriented synthesis on a wide scale. 相似文献
Summary A versatile route to 40-membered library of 2-long alkyl chain substituted benzoazoles (1 and 2) and azole[4,5-b]pyridines (3 and 4) via microwave-assisted combinatorial synthesis was developed. The reactions were carried out in both monomode and multimode microwave
oven. With the latter, all reactions were performed in high-throughput experimental settings consisting of an 8×5 combinatorial
library designed to synthesize 40 compounds. Each step, from the addition of reagents to the recovery of final products, was
automated. The microwave-assisted N-long chain alkylation reactions of 2-alkyl-1H-benzimidazole (1) and 2-alkyl-1H-benzimidazole[4,5-b] pyridines (3) were also studied. 相似文献
Electrochemically induced catalytic multicomponent transformation of isatins, 3-methyl-2-pyrazolin-5-ones and malononitrile
in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles
with fused functionalized pyrano[2,3-c]pyrazole system in 78–99} yields. The developed efficient electrocatalytic approach to medicinally relevant spirocyclic [indole-3,4′-pyrano[2,3-c]pyrazoles] is beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel example of
facile environmentally benign synthetic concept for electrocatalytic multicomponent reaction strategy. 相似文献
A protocol for the synthesis of N-substituted 2-hydro-4-amino-pyrido[2,3-d]pyrimidin-7(8H)-ones (11) is described. Thus, the formylation of a 2-aminopyridone 12 in 85% formic acid/Ac2O, proceeding via in situ cyclization to the intermediate formamide 13, affords the corresponding 2-hydro-4-oxo-pyridopyrimidine 14, which is converted to a 4-chloro-pyridopyrimidine 15 upon treatment with POCl3. The subsequent transformation to the title compounds is carried by treatment with the corresponding amine in MeOH under
microwave irradiation conditions. 相似文献
Novel fluorescing dyes 1,3,4-triphenyl-6-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-ylmethyl)-1H-pyrazolo[3,4-b]quinoline (K1) and 2-[(2-hydroxyethyl)-(1,3,4-triphenyl-1H-pyrazolo[3,4-b]quinolin-6-ylmethyl)-amino]ethanol (L1) have been synthesized and investigated by the means of steady state and time-resolved fluorescence techniques. These compounds
act as sensors for the fluorescence detection of small inorganic cations (lithium, sodium, barium, magnesium and calcium)
in solvents of different polarities (THF and acetonitrile). The mechanism, which allows application of these compounds as
sensors, is an electron transfer from the electro-donative part of molecule to the acceptor part (fluorophore), which is retarded
upon complexation of the electro-donative part by inorganic cations. We found that crown ether-containing compound is very
sensitive to the addition of any investigated ions but amino alcohol-containing one exhibits better selectivity to the addition
of two-valued cations. Two kinds of the complexes (LM+ and L2M+) were found in the investigated systems. In addition, the dyes may be used as fluorescence indicators in solvents of lower
polarity like tetrahydrofuran. 相似文献
Multibilayer structures of hydrated phospholipids, often considered as model biological membranes, are, from the physical viewpoint, lyotropic liquid crystalline systems undergoing temperature-induced mesomorphic phase transitions. Effects of silver nitrate and urocanic acid on lyotropic phase states of hydrated L-α-dipalmitoylphosphatidylcholine (DPPC) have been studied by small-angle X-ray scattering and differential scanning calorimetry (DSC). Both methods show increase of the main phase-transition temperature (Tm) of hydrated DPPC upon introduction of AgNO3 or urocanic acid, decrease of pre-transition temperature (Tp) in the presence of urocanic acid and its increase in the presence of AgNO3. Thus, urocanic acid widened the ripple-phase temperature region. Silver nitrate caused the appearance of an additional high-temperature peak on DSC thermograms, evidencing phase separation in the system. Both agents caused minor effects on DPPC lipid bilayer repeat distance (D) in gel phase, but resulted in noticeable increase of D in the liquid crystal phase with temperature as compared to undoped DPPC structures. 相似文献
Electron paramagnetic resonance study of the single crystals of two PROXYLs, trans-2,5-bis(4-methylphenyl)-2,5-dimethylpyrrolidine-1-oxy [(±)-1] and trans-2-(4-methylphenyl)-2,5-dimethyl-5-phenylpyrrolidine-1-oxy [(±)-2] was conducted. The obtained spectra were always fitted well by a single Lorentzian. The principal g-values (gx, gy, gz) of (±)-1 and (±)-2 were determined as (2.00990, 2.00639, 2.00266) and (2.01106, 2.00742, 2.00389), respectively. The profiles of half width
at half maximum (HWHM) depending on two polar angles, θ and ϕ, were measured in all directions. The angular profiles of the
exchange interaction (|J0|) were attempted to be estimated by dividing the experimental HWHM by the calculated total second moment (M2tot) with the crystallographic data. For (±)-1, |J0| along the c-axis was estimated to be much larger than that along the a- or b-axis. This suggests that (±)-1 is a one-dimensional magnet along the c-axis.
Authors' address: Yohei Noda, Electron Spin Chemistry Laboratory, Department of Chemistry, Graduate School of Science, Kyoto
University, 606-8502 Kyoto, Japan 相似文献
In this paper are presented absorption and fluorescence emission properties of 3-styrylindoles viz. 3-(2-phenylethenyl-E)-NH-indole (1), 3-[2-(4-nitrophenyl)ethenyl-E)-NH-indole (2), 3-[2-(4-cyanophenyl)ethenyl-E]-N-ethylindole (3) and 3-[2-(4-cyanophenyl)ethenyl-E]-NH-indole (4) in organic solvents, 1,4-dioxane-water binary mixtures and micelles (SDS, CTAB and Triton-X-100). The fluorescence properties
of 2-4 have been utilized to probe the microenvironment (binding constant, CMC, micropolarity and solubilization site) of the micelles. 相似文献
A rapid and efficient method for the synthesis of novel dipyrazolo[3,4-b:3′,4′-d]pyridines (DPP) from pyrazolo[3,4-b]pyridine was successfully developed. The DPP derivative was further N-alkylated (6, 8) as well as N-linked with amino acids (13) and their photophysical properties were studied along with N-aryl DPP 4 and observed that the chromophores at C4 position in the aryl ring changed the absorption and emission λmax. 相似文献
Design of stable heavier carbene analogues M(II) (M = Ge, Sn, Pb) with structural motifs different from the traditional di-coordinate analogues is extremely of interest and challengeable. In this paper, we computationally designed a novel class of tri-coordinate cyclic heavier analogues of carbenes covering a number of substituents, i.e., RM(μ-R)2AlR2 (M = Ge, Sn, Pb) 1, in which two sets of inter-molecular donor–acceptor interactions were formed between the di-coordinate carbene MR2 and the AlR3 moiety. The M-centre was found to undergo both the nucleophilic and insertion reactions, indicative of the ‘carbene’ character. We also designed c-1 starting from the known di-coordinate cyclic MR2 and AlR3 under 16 kinds of substituents [NR′2, OR′, PR′2, SR′(R′ = H, Me, iPr, Ph)]; c-1 also has favourable thermodynamic stability. After the only known cyclic tri-coordinate M(II) [M2,R4] inter-molecularly formed between two di-coordinate MR2, the presently designed new tri-coordinate cyclic heavier carbene analogues should expand the higher coordinate M(II) family and await future laboratory synthesis. 相似文献
A 1H-azeto[2,1-d][1,5]benzothiazepin-1-one, -lactam derivatives of dihydrobenzothiazepines library derived from reactions of 2,4-disubstituted 2,3-dihydro-1,5-benzothiazepines and acyl chlorides, including phthalimidoacetyl chloride, chloroacetyl chloride, dichloroacetyl chloride and phenoxyacetyl chloride, was built up through parallel solution-phase synthesis. Stereochemistry of 1H-azeto[2,1-d][1,5]benzothiazepin-1-ones in the reaction process is discussed. 相似文献