酰胺类喹唑啉酮衍生物的合成及抗菌活性

本文设计并合成了23个含酰胺结构单元的新型喹唑啉酮类化合物,经1 H NMR、13 C NMR和HRMS确证结构.在100μg·mL-1和50μg·mL-1浓度下,评价了它们对水稻白叶枯病菌、猕猴桃溃疡病菌和柑橘溃疡病菌的抑菌活性.结果表明,化合物对柑橘溃疡病菌有较强的抑制活性,并测定了6个化合物对柑橘溃疡病菌的EC5...     

Synthesis and photochromism of spirobenzopyrans and spirobenzothiapyran derivatives bearing monoazathiacrown ethers and noncyclic analogues in the presence of metal ions

Spirobenzopyrans bearing monoazathiacrown ethers and noncyclic analogues were synthesized, and their ion-responsive photochromism depending on the dual metal ion interaction with the crown ether and the phenolate anion moieties was examined using alkali and alkaline-earth metal ions, Ag(+), Tl(+), Pb(2+), Hg(2+), and Zn(2+). The prepared spirobenzopyrans showed a selective binding ability to Mg(2+) and Ag(+) with negative and positive photochromism, respectively. Among the metal ions, only Ag(+) facilitated photoisomerization to the corresponding merocyanine form. Depending on the ring size of the monoazathiacrown ether moieties, soft metal ions such as Hg(2+) and Ag(+) showed significant shifts in the UV-vis absorption spectra, while hard metal ions such as Mg(2+), Zn(2+), and Pb(2+) did not afford any meaningful shift. This result reflects that the monoazathiacrown ether and phenolate anion moieties prefer soft and hard metal ions, respectively. Therefore, the Mg(2+) and Ag(+) selectivities are mainly derived from the phenolate anion and monoazathiacrown ether moieties, respectively. On the other hand, a spirobenzothiapyran bearing 3,9-dithia-6-monoazaundecane showed a remarkable selectivity to Ag(+).     

含N-取代哌嗪片段的查尔酮衍生物的合成及其细胞毒活性

以4-甲氧基苯甲醛与2-溴-4’-氟苯乙酮为原料,经缩合、取代反应后,再与α-溴代酮或α-溴代酯反应,合成得到8个查尔酮哌嗪衍生物(3a~3h),其结构经1H NMR、13C NMR和HRMS确证。采用MTT法初步测试了所合成化合物的体外细胞毒活性,结果表明,哌嗪环上含酮基取代的化合物对肿瘤细胞株A549和SGC7901均表现出良好的抑制活性,特别是化合物3a(IC50=0.28μmol/L,2.53μmol/L)活性最高,值得进一步深入研究。     

Synthesis and characterization of new thiadiazole derivatives bearing a pyrazole moiety

A series of thidiazole derivatives (4, 7) from pyrazole-3-carboxylic acid chloride (2) and pyrazole-3,4-dicarboxylic acid chloride derivatives (6) were synthesized and characterized. The structures of the new compounds were confirmed byelemental analysis, NMR (¹H and ¹³C) and IR spectra. The molecular and crystal structure of 4-benzoyl-N-[5-(methylthio)-1,3,4-thiadiazol-2-yl]-1,5-di-phenyl-1H-pyrazole-3-carboxamide(4d)was determined by single crystal X-ray diffraction method.     

Synthesis and antiviral activities of novel 1,4-pentadien-3-one derivatives bearing an emodin moiety

A series of 1,5-diaryl-1,4-pentadien-3-one derivatives bearing an emodin group were designed and synthesized by the combination of natural products. The antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) in vivo were evaluated. Some of the derivatives displayed promising curative effect and protective activity against TMV. Compound D5 showed appreciable curative bioactivity on TMV approximately of 50% at 306.2 mg/mL, which was superior to ningnanmycin (409.3 mg/mL).     

Synthesis and photochromism of polymer-bound phenoxyquinone derivatives

Acrylate- and styrene-derived polymers having pendant phenoxyquinones for photochromism were prepared by 2,2′-azoisobutyronitrile (AIBN)-initiated radical polymerization. Synthesis of the monomers were straightforward and the polymers were obtained in high yields in spite of the quinone moieties presented in the monomers, which usually can function as radical scavengers and/or catalysts poison. Photo-induced rearrangement from the “trans”-quinone forms to the “ana”-quinone forms readily occurred when the polymer films were irradiated with UV light.     

Synthesis and biological activities of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety

A series of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety were designed, synthesized and evaluated for their antibacterial, antifungal and antiviral activities. The bioassay results indicated that most of target compounds showed good antiviral activities against tobacco mosaic virus (TMV) and antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). Especially, the anti-Xoo effect of title compounds 5k (N-(5-methoxybenzo[d]thiazol-2-yl)-2-((5-(2-tolyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) and the anti-Rs effect of title compounds 5a (N-(5-nitrobenzo[d]thiazol-2-yl)-2-((5-(4-(trifluorom ethyl)phenyl)-1,3,4-thiadiazol-2-yl)thio)acetmide) respectively reached 52.4% and 71.6% at 100?µg/mL, which are superior to that of bismerthiazol (32.0% and 52.3%). In addition, the protective and inactivation activities of title compound 5i (N-(5-methoxybenzo [d]thiazol-2-yl)-2-((5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) against TMV were 79.5% and 88.3%, respectively, which are better than that of ningnanmycin (76.4% and 86.8%). The above research showed that benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety may be used as potential molecular templates in searching for highly-efficient antiviral and antibacterial agents.     

Synthesis and antibacterial evaluation of new sulfanyltetrazole derivatives bearing piperidine dithiocarbamate moiety

A series of new alkyl or aryl sulfanyltetrazole derivatives containing dithiocarbamate moiety (5a–6e) were synthesized. The structures of the compounds were characterized by IR, ¹H NMR, ¹³C NMR spectra, and elemental analysis data. The present study examines the antibacterial potential of novel synthetic sulfanyltetrazole compounds against clinically important gram-positive and -negative strains. The results of screening showed that attachment of dithiocarbamate to sulfanyltetrazole derivatives results in enhancement of antibacterial activity. The compound 6d showed the best activity among the tested compounds. Also, the less polar 2,5-disubstituted sulfanyltetrazole regioisomers showed an increased antibacterial activity compared with the corresponding more polar regioisomers.     

Synthesis and antimicrobial activity of some acridone derivatives bearing 1,3,4-oxadiazole moiety

Novel acridone derivatives bearing 1,3,4-moiety were synthesized by intramolecular cyclization of N´-[2-(9-oxoacridin-10(9H)-yl)acetyl]arylhydrazides. Study of antimicrobial activity of the synthesized compounds reveals that some of them are more active than the comparator drug rivanol.     

Oligoether derivatives of 1-phenoxyanthraquinone: Synthesis,photochromism, and complex formation with metal cations

1-Phenoxyanthraquinone isomeric conjugates with tetraethylene glycol were prepared. Their photochromic properties and complex formation in solutions were quantitatively studied by spectrophotometry, quantum yields of the arylotropic photoisomerism and stability constants of complexes between para–ana-quinoid isomers and metal cations. The photochemical migration of a phenyl group considerably affects the complex stability thus providing the possibility to regard the synthesized compounds as photocontrolled ionophores. The structure of some complexes was investigated by X-ray diffraction (XRD) analysis and quantum-chemical simulation.     

Synthesis and cytotoxicity of novel chromenone derivatives bearing 4-nitrophenoxy phenyl acryloyl moiety

This work describes synthesis of novel chromenone derivatives bearing 4-nitrophenoxy phenyl acryloyl moiety through the reaction of 4-(4-nitrophenoxy)benzaldehydes and 3-acetyl-2H-chromen-2-ones in refluxing toluene. Cytotoxicity of all compounds was evaluated using a tetrazolium (MTT) colorimetric assay against human breast cancer cell line, MDA-MB-231.     

Synthesis and in vitro antimicrobial activity of N-arylquinoline derivatives bearing 2-morpholinoquinoline moiety

A new series of N-arylquinoline derivatives 5a-x bearing 2-morpholinoquinoline moiety has been synthesized by one pot base catalyzed cyclocondensation reaction of 2-morpholinoquinoline-3-carbaldehydes 2a-c,malononitrile 3 andβ-enaminones 4a-h. All the synthesized compounds were screened for their in vitro antimicrobial activity against six bacterial pathogens,namely Streptococcus pneumoniae,Clostridium tetani,Bacillus subtilis,Salmonella typhi,Vibrio cholerae,Escherichia coli and against two fungal pathogens,Aspergillus fumigatus and Candida albicans using broth microdilution MIC method.Of the compounds studied,majority of the compounds were found to active against C.tetani,B.subtilis and C.albicans as compared to first-line standard drugs.     

Substituted-nicotinyl thiourea derivatives bearing pyrimidine moiety: synthesis and biological evaluation

A series of substituted-nicotinyl thiourea derivatives containing pyrimidine ring were synthesized in good to excellent yield using PEG-400 as solid?Cliquid phase transfer catalyst under ultrasonic irradiation. The structures of all newly synthesized compounds were elucidated and confirmed by IR, ¹H NMR and elemental analysis. The preliminary biological tests show that some of the target compounds present good inhibitory activities against the root and stalk of dicotyledon plants and are safe for monocotyledon plants.     

Synthesis and antimicrobial activities evaluation of some new thiadiazinone and thiadiazepinone derivatives bearing sulfonamide moiety

A new series of novel functionalized 1,3,4-thiadiazin-5-ones and 1,3,4-thiadi-azepin-5-ones bearing sulfonamide moieties were synthesized via 1,3-dipolar cyclocondensation reaction of nitrilimines with α-mercaptoesters and mercaptosuccinic acid respectively. The structures of the prepared compounds were confirmed by spectral methods (IR, ¹H-NMR, ¹³C-NMR and MS spectroscopy) and elemental analysis. The newly synthesized compounds were screened for their in vitro antimicrobial activity. Some of titled compounds exhibited significant antimicrobial activity on several strains of microbes.     

Synthesis and insecticidal activities of novel neonicotinoid analogs bearing an amide moiety

A series of novel neonicotinoid analogs containing an amide moiety were synthesized, characterized, and subsequently evaluated for their insecticidal activity. According to the preliminary bioassay, the compounds 6c , 6e , 6f , 6j , 6n , and 6r exhibited > 50% activity against Nilaparvata lugens at 100 mg/L. Amongst the active compounds, 6f and 6r revealed insecticidal activities similar to that displayed by standard buprofezin. J. Heterocyclic Chem., (2011)     

Synthesis and in vitro anticancer activity of some novel tetrahydroquinoline derivatives bearing pyrazol and hydrazide moiety

A new series of tetrahydroquinoline derivatives having pyrazol and hydrazide moieties were synthesized for the purpose of anticancer cell line evaluation. Syntheses of these compounds were firstly achieved by one pot four reactions. The reaction of 3-amino-tetrahydro-1H-pyrazolo [3,4-b]quinolin with aldehydes, indoline-2,3-dione derivatives to give 9a-c , 11a-c , and 13a,b , respectively. In similar manner for biological comparison, the reactions of compound 5 with the same aldehydes and indoline-2,3-dione derivatives to give 19a-c and 20a-c . The newly synthesized compounds were examined in vitro for their cytotoxic activity against HepG-2 and A549 cancer cells. The compounds 11a-c and 20a-c showed promising activity as anticancer agents against HepG-2 and A549 cancer cells.     

Synthesis and the effects of substitution upon photochromic diarylethenes bearing an isoxazole moiety

A new class of unsymmetrical photochromic diarylethenes bearing an isoxazole moiety was synthesized and the effects of substitution on their optical and electrochemical properties were investigated systematically. Each of the compounds exhibited remarkable photochromism and functioned as a fluorescent photoswitch both in solution and in poly(methyl methacrylate) films. The electron-donating substituents effectively shifted the absorption maximum and the emission peak to a longer wavelength direction, while the electron-withdrawing substituents notably enhanced the fluorescent quantum yields and oxidation onsets of these diarylethene derivatives. As compared to the unsubstituted parent diarylethene, introduction of the electron-donating/withdrawing substituents could efficiently modulate the optical and electrochemical properties of the diarylethenes bearing an isoxazole moiety. All results indicated that the isoxazole moiety and the substitution effects played a very important role during the process of photochromic reaction for these diarylethene derivatives.     

Synthesis and characterization of p-phenylenediamine derivatives bearing an electron-acceptor unit

[reaction: see text] Two series of aniline oligomers bearing fused heterocycles as an electron-acceptor unit were synthesized. They consist of aniline or its derivatives as an electron donor and benzothiadiazole (BT) or quinoxaline (QX) as an electron-acceptor unit. Benzothiadiazoles 1-3 were synthesized by palladium-catalyzed amination. Quinoxalines 4-6 were prepared by palladium-catalyzed amination or transformation from the benzothiadiazoles. These compounds showed a HOMO-LUMO gap smaller than those of their analogues such as thiophene-substituted BT/QXs. Cyclic voltammetry revealed that the electrochemical behavior is dependent on the position of the acceptor heterocycle. Chemical oxidation with Ag2O afforded the corresponding 1,4-quinonediimine derivatives as an E,E-isomer, stereoselectively. As for the BT pentamer analogues 2 and 3, the first oxidation selectively occurred at the amino group adjacent to the benzothiadiazole unit, giving the regiospecific half-oxidized derivatives. Furthermore, the fully oxidized derivative 24 was isolated and characterized.     

Synthesis and biological evaluation of colchicine and thiocolchicine derivatives bearing a Michael acceptor moiety in ring A

Russian Chemical Bulletin - A series of colchicine and thiocolchicine derivatives bearing a Michael acceptor moiety in ring A were synthesized. Some of these compounds exhibit cytotoxic activity in...