Synthesis and photophysical studies of novel 2-[5-(4-diethylaminophenyl)thiophen-2-yl]quinazoline derivatives

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Synthesis,spectral and electrochemical properties of halogenated 6-alkyl-5-aryl-1-(benzo[d]thiazol-2-yl)-3-phenylverdazyls and 5-aryl-1-(benzo[d]thiazol-2-yl)-3-phenyl-6-vinylverdazyls

Chemistry of Heterocyclic Compounds - A sequence of alkylation, cyclization, and oxidation reactions was used to convert 5-aryl-1-(benzo[d]thiazol-2-yl)-3-phenylformazans into...     

Synthesis of 2-N-(benzo[b]thiophen-2-yl)benzo and heterofused-1,2,3-triazoles

A novel efficient synthesis of 2-N-(benzo[b]thiophen-2-yl)benzo and heterofused-1,2,3-triazoles was achieved by the diazotisation of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile and ethyl-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate and coupling with selected aromatic and heterocyclic amines followed by air oxidation in the presence of cupric acetate.     

Synthesis,Crystal Structure and Antiproliferative Activity of 2-（（（5-（（（5,7-Dimethyl-[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl）thio）methyl）-4-phenyl-4H-1,2,4-triazol-3-yl）thio）methyl）-4Hchromen-4-one Methanol Solvate

The novel crystal of the title compound 2-(((5-(((5,7-dimethyl-[1,2,4]triazolo-[1, 5-a]-pyrimidin-2-yl)thio)methyl)-4-phenyl-4H-1,2,4-triazol-3-yl)thio)methyl)-4H-chromen-4-one methanol solvate(C27H25N7O3S2, Mr = 559.66) has been prepared and its structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monocline system, space group P21/c with a = 11.9879(9), b = 14.0743(10), c = 15.9706(11), β = 98.509(2)°, V = 2664.9(3)3, Z = 4, Dc = 1.395 g/cm3, F(000) = 1168, μ = 0.116 mm-1, MoKa radiation(λ = 0.71073), R = 0.0652, and wR = 0.1425 for 5220 observed reflections with I 2σ(I). X-ray diffraction analyses reveal that the molecule adopts a C-shape. The planes of the benzopyrone and triazolopyrimidine were nearly parallel to each other, with a dihedral angle of 1.21(3)°. Intramolecular and intermolecular hydrogen bonds together with π-π interations are found to exist in the structure. The results of MTT assay indicate that the title compound displays excellent antiproliferative activity against two human cancer cell lines.     

5-甲基-2-苯基-3-噻吩基-7-噻吩亚甲基-3,3a,4,5,6,7-六氢吡唑并[4,3-c]吡啶的微波合成和结构表征

标题化合物(C22H21N3S2)以3,5-二-(2-噻吩基)-1-甲基哌啶-4-酮、苯肼为原料,乙二醇为溶剂,在微波辐射下合成得到.其结构通过单晶X射线衍射法确定,属三斜晶系,空间群P1,相对分子质量Mr=391.54,晶胞参数a=0.804 14(10)nm,b=2.993 9(3)nm,c=0.851360(11)nm,V=1.956 9(3)nm3,Z=4,晶胞密度Dc=1.329 g/cm3,吸收系数μ=0.284 mm-1,单胞中电子的数目F(000)=824.晶体结构用直接法解出,经全矩阵最小二乘法对原子参数进行修正,最终的偏离因子为R=0.072 7,ωR=0.087 8.     

Synthesis of 2-[2-(5-phenyl-1,2,4-oxadiazol-3-yl)-ethyl]benzimidazole and its x-ray analysis

Cyclization of O-benzoyl-2-(benzimidazol-1-yl)propioamidoxime under different temperature conditions gave 2-[2-(5-phenyl-1,2,4-oxadiazol-3-yl)ethyl]benzimidazole whose structure has been determined by X-ray analysis. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1057–1061, July, 2006.     

Synthesis and Crystal Structure of (Z)-N-(2-(diethylamino)ethyl)-7-(5-fluoro-2-oxoindolin-3-ylidene)-2-methyl-4,5,6,7-tetrahydro-1H-indole-3-carboxamide Methanol Solvate

The crystal structure of a new compound (Z)-N-(2-(diethylamino)ethyl)-7-(5- fluoro-2-oxoindolin-3-ylidene)-2-methyl-4,5,6,7-tetrahydro-1H-indole-3-carboxamidemethanol solvate (C24H29FN4O2CH4O, Mr = 456.55) has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group P21/c with a = 14.560(3), b = 7.3200(2), c = 22.233(4) , β = 101.78(3)°, V = 2319.7(8) 3 , Z = 4, Dc = 1.307 g/cm 3 , F(000) = 976, μ = 0.092 mm -1 , MoKa radiation (λ = 0.71073), R = 0.0604 and wR = 0.1644 for 4262 observed reflections with I > 2 (I). X-ray diffraction analysis reveals that the indole and pyrrole are almost coplanar. Intramolecular C-H···O and N-H···O hydrogen bonds together with π-π interactions are found in the structure.     

Synthesis,photophysical and electrochemical properties of novel 6,12-di(thiophen-2-yl) substituted indolo[3,2-b]carbazoles

Novel 5,11-dialkyl-6,12-di(thiophen-2-yl) substituted 5,11-dihydroindolo[3,2-b]carbazoles have been obtained and plausible ways for their further modifications via the Friedel–Crafts reaction are presented. The formylation of these indolo[3,2-b]carbazoles with dichloromethyl alkyl esters catalysed by Lewis acids leads to the formation of the corresponding 2,8-diformyl derivatives. Applicability of this formylation method for modification of indolo[3,2-b]carbazoles bearing electron-rich aromatic substituents at C-6 and C-12 has also been demonstrated. The Knoevenagel condensation of 2,8-dialdehydes with active methylene nitriles has been studied. The measurements of optical and redox properties for a number of new indolo[3,2-b]carbazoles have been performed.     

A Homoleptic KrF2 Complex, [Hg(KrF2)8][AsF6]2⋅2 HF

The reaction of Hg(AsF₆)₂ with a large molar excess of KrF₂ in anhydrous HF has afforded the first homoleptic KrF₂ coordination complex of a metal cation, [Hg(KrF₂)₈][AsF₆]₂?2 HF. The [Hg(KrF₂)₈]²⁺ dication is well‐isolated in the low‐temperature crystal structure of its HF‐solvated [AsF₆]^? salt, and consists of eight KrF₂ molecules that are terminally coordinated to Hg²⁺ by means of Hg?F(KrF) bonds to form a slightly distorted, square‐antiprismatic coordination sphere around mercury. The Raman spectrum of [Hg(KrF₂)₈]²⁺ was assigned with the aid of calculated gas‐phase vibrational frequencies. Computational studies indicate that both electrostatic and orbital interactions are important for metal–ligand bonding and provide insight into the geometry of the [Hg(KrF₂)₈]²⁺ cation and the nature of noble‐gas difluoride ligand bonding.     

Synthesis and Molecular Structure of 5-Amino-7-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydro-1H-indene-4,6-dicarbonitrile

The title compound, C18H13N3O2, has been synthesized for the first time by the multicomponent reaction of cyclopentanone, malononitrile and benzo[d][1,3]dioxole-5-carbalde-hyde in the presence of triethylamine. The structure has been determined by NMR, MS and single-crystal X-ray diffraction. The crystal belongs to the triclinic system, space group P with a = 10.476(5), b = 10.973(5), c = 13.825(5), α = 87.244(5), β = 73.296(5), γ = 82.097(5)°, C18H13N3O2, Mr = 303.31, V = 1507.6(11) 3, Z = 4, Dc = 1.336 g/cm3, F(000) = 632, μ = 0.090 mm-1, R = 0.0431 and wR = 0.1051. There exist intermolecular N-H…N hydrogen bonds in the title compound.     

Synthesis,computational, molecular docking studies and photophysical properties of (Z)-N-(pyrimidin-2-yl)-4-(thiophen-2-ylmethylene)amino) benzenesulfonamide

The (Z)-N-(pyrimidin-2-yl)-4-(thiophen-2-ylmethylene)amino) benzenesulfonamide (TH2DA) were synthesized and characterized by the Infrared, UV–Visible, and NMR analysis. Using density functional theory, the current work is a set of theoretical studies on TH2DA. The compound molecular structure and geometry were defined using DFT. Topological studies, like ELF, LOL, ALIE, and RDG studies, were done with the Multiwfn-3.8 to find the main binding areas and weak interactions in the molecule. Using the IEFPCM solvation model were used to study the calculated UV–Visible spectrum. The HOMO-LUMO, MEP, and NLO properties were carried out in the gas phase. The NBO calculations are used to study how charges move between and within the molecule and stability of this molecule. A pharmacological analysis is done using online tool like Swiss-ADME, to see if the molecule could be potential drug candidate; this evaluation looks at the drug-likeness, ADME and eco-friendly toxicity properties of the TH2DA molecule. Auto-dock suite and Discovery studio Visualizer are used to do molecular docking studies.     

Synthesis of 5-phenylpyrrolo[1,2-b][1,2,5]-triazepin-2(3H)-ones

The synthesis of a series of 5-phenylpyrrolo[1,2-b][1,2,5]triazepin-2(3H)-ones 1 as potential anxiolytic agents is described. Benzoylation of 1-phthalimidopyrrole, followed by hydrolysis, gave the 1-amino-2-benzoylpyrroles 3 . These were further functionalized to give the penultimate 1-aminoacetamido-2-benzoylpyrroles 8 and 9 , which were cyclized to the target pyrrolotriazepines 1.     

Synthesis, electrochemical properties, and thermal transformations of 1-(5-nitropyrimidin-2-yl)[60]fullereno[1,2-b]aziridine

The reaction of fullerene C₆₀ with 2-azido-5-nitropyrimidine afforded 1-(5-nitropyrimidin-2-yl)[60]fullereno[1,2-b]aziridine, whose electrochemical reduction proceeds more easily than the reduction of nonmodified C₆₀. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 484–488, March, 2006.     

New 3-(4-arylpiperazin-1-yl)-1-(benzo[b]thiophen-3-yl)-2-methylpropanol derivatives:Synthesis and evaluation for dual 5-HT1A/SSRI activities

A series of 3-(4-arylpiperazin-1-yl)-l-(benzo[b]thiopben-3-yl)-2-methylpropanol derivatives were designed and synthesized based on 5-HT1A/SSRI drugs design strategies.The synthesized compounds were evaluated for their dual 5-HT1A/5-HTT activities.     

New 3-（4-arylpiperazin-1-yl）-1-（benzo[b]thiophen-3-yl）-2-methylpropanol derivatives：Synthesis and evaluation for dual 5-HT1A/SSRI activities

A series of 3-（4-arylpiperazin-1-yl）-1-（benzo[b]thiophen-3-yl）-2-methylpropanol derivatives were designed and synthesized based on 5-HT1A/SSRI drugs design strategies.The synthesized compounds were evaluated for their dual 5-HT1A/5-HTT activities.     

Light-induced structural changes in (HgBr2)3(As4S4)2: An X-ray single-crystal diffraction,Raman spectroscopy and ab initio study

To investigate the behaviour of the As₄S₄ molecule within a crystal-chemical environment differing from realgar, α-As₄S₄, and its high-temperature polymorph, β-As₄S₄, the effects of the light exposure on the structure of the (HgBr₂)₃(As₄S₄)₂ adduct have been studied. Differently from the cases previously studied, the action of the light filtered using a 550 nm long-wavelength pass filter did not produce any evident effect on the unit-cell. On the other hand, employing the 440 nm long-wavelength pass filter, remarkable variations of the unit-cell parameters were observed. In particular, an increase of the a, c, and β, and a decrease of the b parameter, producing on the whole an expansion of the unit-cell volume, is observed as a function of the light exposure times. Structure refinements indicated that the increase of the unit-cell volume is to ascribe to the formation of an increasing fraction (up to 20%) of pararealgar-type replacing the realgar-type molecule. Further light-exposure did not cause any further increase of the lattice parameters. On the contrary, a decrease of the unit-cell volume occurred by keeping the crystal in the dark (46 days): due to the loss of the crystallinity, only the core of the crystal, less altered and with smaller unit-cell volume, contributes to the diffraction effects. Micro-Raman spectra were collected on crystals exposed to the above mentioned wavelength light for increasing times. The peak at 275(±1) cm⁻¹ whose intensity increases as a function of the exposure time confirms the transition from a realgar- to a pararealgar-type molecule in the (HgBr₂)₃(As₄S₄)₂ adduct. Relativistic DFT-GGA ab initio band structure calculations reveal a direct band gap of 2.04 eV and quite flat valence and conduction bands around the Fermi level. According to analyses of the atomic orbital contributions to the electronic band structures the highest occupied states are attributed to non-bonding p-states of As.     

(5-氨基-[1,3,4]噻二唑-2-基)-丙酸乙酯的合成工艺改进

以丁二酸酐为起始原料,经醇解和酰化反应制得丁二酸单乙酯酰氯(3);3经甲烷磺酸催化与氨基硫脲环合合成了重要药物中间体——(5-氨基-[1,3,4]噻二唑-2-基)-丙酸乙酯,其结构经~1H NMR,IR和MS确证。运用正交试验对环合反应条件进行优化。最优反应条件为:3 132 mmol,n(氨基硫脲)∶n(3)∶n(甲烷磺酸)=1∶3∶3,于110℃反应3 h,总收率51.3%。     

Chiral photochromic 2-(N-acyl-N-arylaminomethylene)benzo[b]thiophen-3(2H)-ones

Photochromic 2-(N-acyl-N-arylaminomethylene)benzo[b]thiophen-3(2H)-ones containing ortho-substituents in the N-phenyl ring were studied by X-ray diffraction analysis and ¹H NMR spectroscopy. It was established that these compounds have stable chiral structures due to hindered rotation of the phenyl ring around the C—N bond. The energy barrier to racemization evaluated by dynamic NMR spectroscopy is G ^# _{428 K} = 98 kJ mol^–1.