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1.
π‐Conjugated organic materials exhibit high and tunable nonlinear optical (NLO) properties, and fast response times. 4′‐Phenyl‐2,2′:6′,2′′‐terpyridine (PTP) is an important N‐heterocyclic ligand involving π‐conjugated systems, however, studies concerning the third‐order NLO properties of terpyridine transition metal complexes are limited. The title binuclear terpyridine CoII complex, bis(μ‐4,4′‐oxydibenzoato)‐κ3O,O′:O′′;κ3O′′:O,O′‐bis[(4′‐phenyl‐2,2′:6′,2′′‐terpyridine‐κ3N,N′,N′′)cobalt(II)], [Co2(C14H8O5)2(C21H15N3)2], (1), has been synthesized under hydrothermal conditions. In the crystal structure, each CoII cation is surrounded by three N atoms of a PTP ligand and three O atoms, two from a bidentate and one from a symmetry‐related monodentate 4,4′‐oxydibenzoate (ODA2−) ligand, completing a distorted octahedral coordination geometry. Neighbouring [Co(PTP)]2+ units are bridged by ODA2− ligands to form a ring‐like structure. The third‐order nonlinear optical (NLO) properties of (1) and PTP were determined in thin films using the Z‐scan technique. The title compound shows a strong third‐order NLO saturable absorption (SA), while PTP exhibits a third‐order NLO reverse saturable absorption (RSA). The absorptive coefficient β of (1) is −37.3 × 10−7 m W−1, which is larger than that (8.96 × 10−7 m W−1) of PTP. The third‐order NLO susceptibility χ(3) values are calculated as 6.01 × 10−8 e.s.u. for (1) and 1.44 × 10−8 e.s.u. for PTP.  相似文献   

2.
A series of compounds, viz. 2‐(3‐(4‐aryl)‐1‐isonicotinoyl‐4,5‐dihydro‐1H‐pyrazol‐4‐yl)‐3‐phenylthiazolidin‐4‐one 4 ( a – n ), have been synthesized by reaction of 3 ( a – n ) with thioglycolic acid in the presence of zinc chloride. Compounds 3 ( a – n ) have been synthesized by amination of formylated pyrazoles 2 ( A – B ), which were synthesized by formylation of 1 ( A – B ) by Vilsmeier–Haack reagent (POCl3/DMF). Compounds 1 ( A – B ) were synthesized by condensation of hydrazide and substituted acetophenones under conventional method and microwave irradiation method. These compounds were identified on the basis of melting point range, Rf values, infrared, 1H NMR, and mass spectral analysis. These compounds were evaluated for their in vitro antimicrobial activity, and their minimum inhibitory concentration was determined. Among them, compound 4b and compound 4l possess appreciable antimicrobial and antifungal activities. Antibacterial activity results showed that compounds containing electron‐withdrawing groups were more active than compounds containing electron‐releasing groups.  相似文献   

3.
A new series of thermotropic liquid‐crystalline (LC) polyesters were prepared from a diacyl chloride derivative of 4,4′‐(terephthaloyldioxy)‐di‐4‐phenylpropionic acid (PTP) and glycols with a different number of methylene groups (n) [HO(CH2)n OH, n = 6–10, 12] by high‐temperature solution polycondensation in diphenyl oxide. PTP6/10 and PTP6/hydroquinone (H) LC copolyesters were also prepared according to a similar procedure. The chemical structure, LC, phase‐transition behaviors, thermal stability, and solubility were characterized by elemental analysis, Fourier transform infrared spectroscopy, 1H and 13C NMR spectra, differential scanning calorimetry (DSC), thermogravimetric analysis, and a polarizing light microscope. The melting and isotropization temperatures decreased in a zigzag manner as the number of n increased. All of the polyesters formed a nematic phase with the exception of PTP8. The temperature ranges of the mesophase (ΔT) were much wider for the polyesters with an odd number of n's than those with an even number. ΔT increased markedly for the PTP6/10 and PTP6/H copolyesters. The in vitro degradations of the polymers were ascertained by enzymatic hydrolysis and alkaline hydrolysis. The model compound, PTP dihexylester, was synthesized and found to be degraded into terephthalic acid, 3‐(4‐hydroxyphenyl)propionic acid, and 1‐hexanol by Rhizopus delemar lipase, but PTPn homopolyesters and PTP6/10 and PTP6/H copolyesters were resistant to Rhizopus delemar hydrolysis. They were degradable in a sodium hydroxide buffer solution of pH 12 at 60 °C, depending on the number of n's and the copolymer composition. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 3043–3051, 2001  相似文献   

4.
Eighteen novel 2‐(1‐aryl‐5‐methyl‐1,2,3‐triazol‐4‐yl)‐1,3,4‐oxadiazole derivatives and two acylhydrazone intermediate compounds were synthesized by various pathways starting from 1‐aryl‐5‐methyl‐1,2,3‐triazol‐4‐formhydrazide ( 1 ). All products were identified by spectroscopic analysis, and 2‐(1‐aryl‐5‐methyl‐1,2,3‐triazol‐4‐yl)‐5‐benzalthio‐1,3,4‐oxadiazole was further validated by X‐ray crystallography. Results from primary antibacterial activity tests indicated that most of the compounds were effective against E. coli, P. aeruginosa, B. subtilis and S. aureus.  相似文献   

5.
A series of novel N‐(2‐(pyridine‐4‐yl)‐1H‐pyrrolo[3,2‐c]‐pyridin‐6‐yl‐(substituted)‐sulfonamide derivatives were synthesized from 2‐bromo‐6‐nitro‐1H‐pyrrolo[3,2‐c]pyridine through a series of reactions including Suzuki reaction, reduction, protection, and sulfonamide coupling. All the synthesized compounds were screened for anticancer activity against MCF‐7, HeLa, A‐549, and Du‐145 cancer cell lines by the MTT assay. The preliminary bioassay suggests that most of the compounds show antiproliferation with different degrees. Doxorubicin was used as a positive control. Among the synthesized compounds, 8d and 8h were most active compared with the standard in cell line data. The synthesized compounds 8d and 8h show IC50 values in the range of 1.88–5.16 μM for all the cell lines. Compounds 8d and 8h were further studied for a panel of eight human kinase at 10 μM concentrations and the result shows 64% to 70% inhibitions for both Aurora‐A and Aurora‐B kinase.  相似文献   

6.
The dual inhibitors against aldose reductase (ALR2) and protein tyrosine phosphatase 1B (PTP1B) may present an anti‐diabetic potency in insulin resistance without risks of serious diabetic complications. Therefore, in the present study, we constructed two separate pharmacophore mapping‐based 3D quantitative structure–activity relationship models for ALR2 (AADRR.11093 with standard deviation 0.663, 0.719, F 22.3, root‐mean‐square error 0.705, 0.647, Pearson‐r 0.802) and PTP1B (AARR.155 with standard deviation 0.146, 0.945, F 82.70, root‐mean‐square error 0.351, 0.621, Pearson‐r 0.831) employing the dataset of 54 flavonoids as ALR2 inhibitors and 46 naphthoquinones as PTP1B inhibitors to identify structural features necessary for the inhibition of both enzymes. These models were subsequently used as 3D query search for hierarchical virtual screening‐based designing using the PHASE database of 1.5 million compounds. Designed dual inhibitors were further subjected to GLIDE XP docking analysis using high‐resolution 3D structures of ALR2 (1US0, at resolution of 0.66 Å) and PTP1B (2F71 at resolution of 1.55 Å) available in the Protein Data Bank to authenticate identified structural features with important binding interactions necessary for dual inhibition. Copyright © 2014 John Wiley & Sons, Ltd.  相似文献   

7.
《中国化学会会志》2018,65(7):810-821
A series of coumarin‐substituted 1,3‐thiazine‐2‐thione derivatives ( 4a–m ) were synthesized via the multicomponent reaction of 3‐chloro‐3‐(2‐oxo‐2H‐chromen‐3‐yl)acrylaldehyde ( 1 ) carbon disulfide ( 2 ), and various primary amines ( 3 ), in presence of triethylamine and acetonitrile under stirring with good yields. The structures of all the synthesized compounds were characterized by analytical and spectral studies. Further, the synthesized compounds were screened for their in vitro antiproliferative activities against different cancer cell lines (A549, MDA‐MB‐231, MCF7, HeLa, and B16F10). Studies on the molecular interactions to recognize the hypothetical binding motif of the title compounds with the target Hsp 100 were carried out employing the Schrodinger software. Compounds 4a , 4c and 4m showed activity against all the five cell lines compared with the reference drug, and 4a exhibited the least IC50 concentration of 7.56 ± 1.07 μg/mL against MCF7. This in vitro anticancer result was supported by in silico docking and in silico ADME (absorption, distribution, metabolism, and excretion) studies as well.  相似文献   

8.
A series of novel N‐(4‐(2‐aryloxythiazol‐5‐yl)but‐3‐yn‐2‐yl)benzamide derivatives were designed and synthesized. Their structures were identified by 1H NMR and elemental analyses. Preliminary bioassays indicated that some title compounds provided >80% control of Sclerotinia sclerotiorum at 50 µg/mL and >70% herbicidal activities against B. campestris at 100 µg/mL. Their structure‐activities relationships were also discussed.  相似文献   

9.
As a powerful synthon, N ′‐(2‐alkynylbenzylidene)hydrazides have been utilized efficiently for the construction of N‐heterocycles. Since N ′‐(2‐alkynylbenzylidene)hydrazides can easily undergo intramolecular 6‐endo cyclization promoted by silver triflate or electrophiles, the resulting isoquinolinium‐2‐yl amides can proceed through subsequent transformations including [3 + 2] cycloaddition, nucleophilic addition, and [3 + 3] cycloaddition. Several unexpected rearrangements via radical processes were observed in some cases, which afforded nitrogen‐containing heterocycles with molecular complexity. Reactive partners including internal alkynes, arynes, ketenimines, ketenes, allenoates, and activated alkenes reacted through [3 + 2] cycloaddition and subsequent aromatization, leading to diverse H‐pyrazolo[5,1‐a]isoquinolines with high efficiency. Nucleophilic addition to the in situ generated isoquinolinium‐2‐yl amide followed by aromatization also produced H‐pyrazolo[5,1‐a]isoquinoline derivatives when terminal alkynes, carbonyls, enamines, and activated methylene compounds were used as nucleophiles. Isoquinoline derivatives were obtained when indoles or phosphites were employed as nucleophiles in the reactions of N ′‐(2‐alkynylbenzylidene)hydrazides. A tandem 6‐endo cyclization and [3 + 3] cycloaddition of cyclopropane‐1,1‐dicarboxylates with N ′‐(2‐alkynylbenzylidene)hydrazides was observed as well. Small libraries of these compounds were constructed. Biological evaluation suggested that some compounds showed promising activities for inhibition of CDC25B, TC‐PTP, HCT‐116, and PTP1B.

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10.
Starting from 1H‐pyrazol, a wide number of 1‐alkyl‐1H‐pyrazol‐4‐yl and 1‐alkyl‐1H‐pyrazol‐5‐ylboronic acids and their pinacol esters were synthesized and characterized. The key step in the described methodology is the regioselective lithiation of the pyrazole ring. The synthesized pinacolates are stable under prolonged storage and can be used as convenient reagents in organic synthesis.  相似文献   

11.
Synthesis of a series of novel class of N‐substituted‐2‐(benzo[d]isoxazol‐3‐ylmethyl)‐1H‐benzimidazoles ( 4 ) by the condensation of o‐phenylenediamine ( 1 ) with benzo[d]isoxazol‐3‐yl‐acetic acid ( 2 ) and subsequent reactions with different types of electrophiles have been reported. Some compounds exhibited promising anti‐bacterial activity against Salmonella typhimurium, however poor activity against Staphylococcus aureus. The compound 4t was found to have high activity even at 1 μg/ml compared to Cephalexin against S. aureus. The biological activity against PDE‐IV for potential anti‐asthmatic effect and against DP‐IV and PTP‐1B for potential anti‐diabetic effects was disappointing.  相似文献   

12.
Two series of novel 4‐acyl‐2,5‐disubstituted‐3‐hydroxypyrazoles 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h and 4‐arylcarbonyl‐3‐substitutedisoxazol‐5‐ones 7a , 7b , 7c , 7d , 7e , 7f , 7g , 7h , 7i were synthesized by the Scotton–Baumann reaction of 2,5‐disubstituted‐2,4‐dihydro‐pyrazol‐3‐ones 1 or 3‐substituted‐4H‐isoxazol‐5‐ones 6 and various acyl chlorides, followed by the Fries rearrangement in the presence of calcium hydroxide and calcium oxide as the catalyst. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. 1H NMR indicated that compounds 3 existed in enol forms and compounds 7 in keto configurations. The results of preliminary bioassays showed that some of the title compounds 3 and 7 exhibited moderate to good herbicidal activities against Brassica campestris L. at the concentration of 100 mg/L. Isoxazole compounds 7 showed better herbicidal activity against B. campestris L. than pyrazole compounds 3 did at the concentration of 100 mg/L. Moreover, most of the isoxazole compounds displayed higher herbicidal activity against B. campestris L. than Echinochloa crus‐galli. However, these compounds showed weak herbicidal activities at the concentration of 10 mg/L.  相似文献   

13.
Series of star‐shaped three arms oligoimides (SOI) with terminal amino groups with narrow MWD ((Mw/Mn = 1.1–2) was synthesized by the one‐stage high‐temperature polycondensation in molten benzoic acid at 140 °C. The (B3+AB′) approach with the “slow addition of monomer” method was used for this synthesis, where B3 is 2,4,6‐tris(4‐aminophenoxy)toluene and AB′ is 3‐aminophenoxy phthalic acid. The SOI arm's length was controlled by the AB′/B3 mole ratio of 10:1, 20:1, 40:1, and 100:1. By the reaction of SOI's terminal amino groups with acetic anhydride, corresponding acetamide derivatives were obtained. SOI synthesized are soluble in selected organic solvents. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56, 2004–2009  相似文献   

14.
A series of new 5‐(1‐aryl‐1H‐pyrazole‐4‐yl)‐1H‐tetrazoles 4a‐l were synthesized via [3 + 2] cycloaddition reaction from 1‐aryl‐1H‐pyrazole‐4‐carbonitriles 3a‐l , sodium azide and ammonium chloride, using dimethylformamide (DMF) as solvent, in good yields: 64–85%. The structures of these newly synthesized compounds were determined from the IR, 1H‐ and 13C‐NMR spectroscopic data and elemental analyses.  相似文献   

15.
This article reports on developing an efficient synthesis approach to aliphatic polyester dendrimer, poly(thioglycerol‐2‐propionate) (PTP), by combination of thio‐bromo “Click” chemistry with atom transfer nitroxide radical coupling (ATNRC). Through the one‐pot two‐step method, linear polystyrene with hydroxyl end groups (l‐PS‐2OH) was obtained by first atom transfer radical polymerization of styrene and following termination using 4‐(2,3‐dihydroxypropoxy)‐TEMPO (DHP‐TEMPO) to capture the PS macroradicals via ATNRC method. Using l‐PS‐2OH as support, the dendritic repeating units divergently were grown from the hydroxyl end groups via esterification and thio‐bromo “Click” reaction two‐step process. In every generation, the resulting intermediates l‐PS‐d‐PTP (G1‐G4) can be easily isolated from the excessive unreacted monomers by simple precipitation in ethanol without help of time, labor and solvent consuming column chromatographic purification. At last, cleavage of the alkoxyamine group between the PS support and dendrimer at elevated temperature (125 °C) provided the targeted polyester dendrimer PTP up to the fourth generation. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015 , 53, 1762–1768  相似文献   

16.
5,6‐Dichloro‐2‐hydroxymethyl‐1H‐benzimidazole ( 1 ) was prepared by the cyclization of 4,5‐dichloro‐o‐phenylenediamine with glycolic acid, then, alcohol group of 1 was converted to carboxylic acid ( 2 ). The final products 5,6‐dichloro‐1H‐benzimidazole‐2‐carboxamides ( 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 13 , 14 ) were prepared by the amidification of compounds 2 with several amines by using O‐(benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium hexafluorophosphate. Compound 12 was prepared by the reaction of compound 6 with methanolic HCl. The relations between the tautomer and nontautomer types of imidazole moiety are discussed with NMR spectroscopy. The in vitro antibacterial and antifungal activity of the synthesized compounds against S. aureus, E. coli, B. subtilis, and C. albicans were evaluated with the disc diffusion techniques. The synthesized compounds were more active against the bacteria than fungi. Compound 3 exhibited best inhibitory activity against S. aureus. J. Heterocyclic Chem., (2011).  相似文献   

17.
15‐Cyano‐12‐oxopentadecano‐15‐lactone was synthesized in 59% total yield starting from 2‐nitrocyclododecanone by Michael addition to acrylaldehyde, followed by reaction with trimethylsilylcyanide, hydrolysis, ring‐expansion, and Nef reaction. A two‐step, one‐pot synthesis of intermediate 2‐hydroxy‐4‐(1‐nitro‐2‐oxycyclododecyl)butanenitrile from 3‐(1‐nitro‐2‐oxocyclododecyl)propanal was developed and the conditions for the Nef reaction were studied. 15‐Cyano‐12‐oxopentadecano‐15‐lactam was synthesized in 40% total yield starting from 2‐nitrocyclododecanone by Michael addition to acrylaldehyde, followed by Strecker reaction, ring‐expansion, and Nef reaction. The conditions for the Strecker and Nef reactions were studied. The structures of the target compounds, intermediates, and by‐product were characterized by IR, 1H‐ and 13C‐NMR, and elemental analysis or MS.  相似文献   

18.
The novel heterocyclizations of ethyl 5‐(hydrazinocarbonyl)‐2,4‐dimethyl‐1H‐pyrrole‐3‐carboxylate are developed. New derivatives of ethyl esters of 4‐R‐6,8‐dimethyl‐1‐oxo‐1,2‐dyhidropyrrolo[1,2‐d][1,2,4]triazine‐7‐carboxylic acids were obtained. The in vitro anticancer and antibacterial activities of the synthesized compounds were revealed. The most potent antibacterial compound appeared to be 1.3 inhibiting Staphylococcus aureus. Pyrrolo[1,2‐d][1,2,4]triazine 2.15 showed significant antifungal activity against Candida tenuis. The anticancer activity of the synthesized compounds was determined.  相似文献   

19.
A series of novel pyrrolo‐allocolchicine derivatives (containing a 1‐methyl‐1H‐indol‐5‐yl moiety replacing ring C) was synthesized. The tetracyclic ring system was constructed by Suzuki–Miyaura cross‐coupling of a 1‐methylindole‐5‐boronate with an ortho‐iodo‐dihydrocinnamic acid derivative and subsequent intramolecular Friedel–Crafts acylation. After reduction of the resulting ketone, the nitrogen functionality was introduced in a Mitsunobu‐type reaction by using zinc azide followed by LiAlH4 reduction. Structural assignments were supported by X‐ray crystallography. The compounds synthesized were then tested against BJAB tumor cells and found to exhibit pronounced cytotoxic activity (proliferation inhibition and apoptosis induction). The ketone 24 b was even active at sub‐nanomolar concentration. In addition, the antitumor potential of the compounds was confirmed by using B lymphoid cell lines.  相似文献   

20.
The chemical reactivity of 4,9‐dimethoxy‐5‐oxo‐5H‐furo[3,2‐g ]chromene‐6‐carboxaldehyde (6‐formylkhellin) ( 1 ) was studied toward a diversity of nitrogen nucleophilic reagents. Reaction of carboxaldehyde 1 with some primary amines and heterocyclic amines afforded the corresponding Schiff bases. Also, the reactivity of carboxaldehyde 1 was studied toward some hydrazine derivatives, namely 7‐chloro‐4‐hydrazinoquinoline, 3‐hydrazino‐5,6‐diphenyl‐1,2,4‐triazine, N4‐phenylthiosemicarbazide, and S‐benzyldithiocarbazate. 6‐Formylkhellin ( 1 ) underwent ring transformation upon treatment with hydroxylamine hydrochloride producing 5‐hydroxy‐4,9‐dimethoxy‐7‐oxo‐7H‐furo[3,2‐g ]chromene‐6‐carbonitrile ( 22 ). Some pyrimidine, [1,2,4]triazolo[4,3‐a ]pyrimidine, tetrazolo[1,5‐a ]pyrimidine, and diazepine derivatives linked benzofuran were efficiently synthesized. Reaction of carboxaldehyde 1 with a variety of 1,4‐binucleophiles produced furochromone‐fused benzodiazepine, pyridotriazepine, benzoxazepine, and benzothiazepine derivatives. Some unsymmetrical thiocarbohydrazones were also synthesized. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.  相似文献   

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