N-苄叉丹皮酚腙的合成及其抗菌活性研究

以中药有效成分丹皮酚 (2-羟基-4-甲氧基苯乙酮)为原料,与水合肼反应得到中间体丹皮酚腙,然后分别与各种取代苯甲醛反应合成了9个N-苄叉丹皮酚腙,产率为50.5%~91.9%。初步探索了合成条件,目标化合物的结构经FT-IR,1H NMR,13C NMR, LC-MS表征。初步探索了合成条件、测定抗菌活性;结果表明：测定结果表明,部分化合物具有良好的抗菌活性,尤其是化合物N-(4-氟苄叉基)丹皮酚腙 (3c) 对金黄色葡萄球菌的MIC为4μg/mL,化合物N-(2-氟苄叉基)丹皮酚腙 (3b) 对大肠杆菌表现出与阳性对照药利福平相当的抗菌效果。     

N-苄叉丹皮酚腙的合成及其抗菌活性

以丹皮酚(2-羟基-4-甲氧基苯乙酮)(Ⅰ)为原料,与水合肼反应得到中间体丹皮酚腙(Ⅱ),然后Ⅱ分别与各种取代苯甲醛反应合成了9个N-苄叉丹皮酚腙(Ⅲa~Ⅲi),产率为50.5%~91.9%。利用FTIR、1HNMR、13CNMR、LC-MS对目标化合物的结构进行了表征。初步探索了Ⅱ和Ⅲ的合成条件、测定了Ⅲa~Ⅲi的抗菌活性。结果表明:化合物N-(4-氟苄叉基)丹皮酚腙(Ⅲc)对金黄色葡萄球菌的最低抑菌浓度(MIC)为2 mg/L,化合物N-(2-氟苄叉基)丹皮酚腙(Ⅲb)对大肠杆菌的MIC为8 mg/L,与阳性对照药利福平抗菌效果相当。     

Synthesis and Antimicrobial Activity of Some Novel Cross-Linked Chitosan Hydrogels

Four novel hydrogels based on chitosan were synthesized via a cross-linking reaction of chitosan with different concentrations of oxalyl bis 4-(2,5-dioxo-2H-pyrrol- 1(5H)-yl)benzamide. Their structures were confirmed by fourier transform infrared X-ray (FTIR), scanning electron microscopy (SEM) and X-ray diffraction. The antimicrobial activities of the hydrogels against two crop-threatening pathogenic fungi namely: Aspergillus fumigatus (A. fumigatus, RCMBA 06002), and Aspergillus niger (A. niger, RCMBA 06106), and five bacterial species namely: Bacillis subtilis (B. subtilis, RCMBA 6005), Staphylococcus aureus (S. aureus, RCMBA 2004), Streptococcus pneumoniae (S. pneumonia, RCMB 000101) as Gram positive bacteria, and Salmonella typhimurium (S. typhimurium, RCMB 000104), and Escherichia coli (E. coli, RCMBA 5003) as Gram negative bacteria have been investigated. The prepared hydrogels showed much higher antimicrobial activities than that of the parent chitosan. The hydrogels were more potent in case of Gram-positive bacteria than Gram-negative bacteria. Increasing the degree of cross-linking in the hydrogels resulted in a weaker antimicrobial activity.     

Synthesis and Antimicrobial Activity of Boron-doped Titania Nano-materlals

Antibacterial activity of boron-doped TiO2 （B/TiO2） nano-materials under visible light irradiation and in the dark was investigated. A simple sol-gel method was used to synthesize TiO2 nano-materials. X-ray diffraction pattern of B/TiO2 nano-materials represents the diffraction peaks relating to the crystal planes of TiO2 （anatase and rutile）. X-ray photoelectron spectroscopy result shows that part of boron ions incorporates into TiO2 lattice to form a possible chemical environment like Ti-O-B and the rest exist in the form of B2O3. The study on antibacterial effect of B/TiO2 nano-materials on fungal Candida albicans （ATCC10231）, Gram-negative Escherichia coli （ATCC25922） and Gram-positive Staphylococcus aureus （ATCC6538） shows that the antibacterial action is more significant on Candida albicans than on Escherichia coli and Staphylococcus aureus. Under visible light irradiation, the antibacterial activity is superior to that in the dark.     

新型双酰胺衍生物的合成及抗癌活性

以取代苯甲酸为起始原料,设计合成了10个含苯并噻唑基双酰胺类化合物,其结构经1HNMR、13CNMR、IR及元素分析确证。采用MTT法进行化合物抑制PC3、BGC-823癌细胞体外活性测试,结果表明,所合成的化合物具有不同程度地抑制癌细胞活性,其中化合物N-[2-(6-甲基苯并噻唑-2-氨基甲酰基)-4-甲基苯基]-4-氯苯甲酰胺(Ⅳa)和N-[2-(4-甲基苯并噻唑-2-氨基甲酰基)-4-甲基苯基]-2-甲基苯甲酰胺(Ⅳe)在10μmol/L浓度下对PC3的抑制率为70.8%和68.4%,N-[2-(苯并噻唑-2-氨基甲酰基)-4-甲基苯基]-2-甲基苯甲酰胺(Ⅳd)在10μmol/L浓度下对BGC-823的抑制率为65.9%。     

芳基胍碳酸盐的合成及抗菌活性初步研究

以芳胺为原料在酸性条件下与单氰胺作用得到11个芳基胍碳酸盐。化合物结构经IR、MS和1H NMR确证。抗菌活性实验表明此类化合物有一定的抑菌作用,供电子基团有利于抑菌活性的提高。     

Synthesis,Surface Activity and Aggregation Behavior of Novel Gemini Pyridinium Amphiphiles

A series of novel pyridinium cationic gemini amphiphiles, 3,3′-(carbonyldiimino)bis (1-n-alkylpyridinium) dibromides, having octyl, decyl, dodecyl, tetradecyl alkyl chains were synthesized. The surface properties and aggregation behavior in aqueous solution were evaluated by surface tension, dynamic light scattering (DLS), and transmission electron microscopy (TEM) measurement. The adsorption at the air/solution interface of all the compounds were quantitative described using the Frumkin model, and the effect of alkyl chain length on surface activity and aggregate behavior was analyzed. It was found that all the gemini amphiphiles possess surface activity and low critical micellization concentration (CMC) values. The values of log CMC depended linearly on the carbon number of the alkyl chains, but the surface tension at the CMC (γ_cmc) showed a minimum for the compound with dodecyl chains. Combinations of DLS and TEM observations showed the existence of vesicles with a broad size distribution in aqueous solution. Meanwhile, vesicles formed below the CMC could be a possible reason for the observed deviation of surface tension curves from the Frumkin model.     

新型双季铵盐杀菌剂的合成和杀菌性能研究

本文合成了以两个吡啶环为核心,通过链桥结构联接,每个分子含有两个正电荷N 离子,及两个亲水和疏水基团的一种新型双季铵盐,通过微生物杀菌试验,表现出良好的杀菌性能。     

Antimicrobial and Anticancer Properties of Synthetic Peptides Derived from the Wasp Parachartergus fraternus

Agelaia-MPI and protonectin are antimicrobial peptides isolated from the wasp Parachartergus fraternus that show antimicrobial and neuroactive activities. Previously, two analogues of these peptides, neuroVAL and protonectin-F, were designed to reduce nonspecific toxicity and improve potency. Here, the three-dimensional structures of neuroVAL, protonectin and protonectin-F were determined by using circular dichroism and NMR spectroscopy. Antibacterial, antifungal, cytotoxic and hemolytic activities were tested for the parent peptides and analogues. All peptides showed moderate antimicrobial activity against Gram-positive bacteria, with agelaia-MPI being the most active. Protonectin and protonectin-F were found to be toxic to cancerous and noncancerous cell lines. Internalization experiments revealed that these peptides accumulate inside both cell types. By contrast, neuroVAL was nontoxic to all tested cells and was able to enter cells without accumulating. In summary, neuroVAL has potential as a nontoxic cell-penetrating peptide, while protonectin-F needs further modification to realize its potential as an antitumor peptide.     

反丁烯二酸桂醇甲酯的合成及抗菌活性研究

以α,β-不饱和羰基结构为母体合成对皮肤无致敏性的反丁烯二酸桂醇甲酯(CMF)。合成实验表明:顺丁烯二酸酐与肉桂醇等摩尔混合,90℃反应2.5h后加入异构化催化剂在90℃反应4h转型,甲酯化反应以甲醇与桂醇单酯的摩尔比为6:1,在90℃恒温反应4h得率较高。抗菌活性实验表明:反丁烯二酸桂醇甲酯不但杀菌谱广,而且有效作用浓度低。在食品加工、保藏中具有广阔的开发应用前景。     

Polyetherketones: Synthesis,Characterization and Antimicrobial Activity

ABSTRACT

Friedel-Crafts polyetherketones were prepared from o-chlorophenol, 1,4-phenylenedioxy diacetylchloride (1,4-PDC), chloroacetyl chloride (CAC), 1,2-dichloroethane (DCE), and dichloromethane (DCM) using anhydrous aluminium chloride (AlCl₃) as catalyst and carbon disulfide (CS₂) as solvent. These resins were characterized by IR spectroscopy and gel permeation chromatography. Carius method was employed to obtain the percentage of chlorine content in the resins. The kinetic parameters for the thermal behavior of the resins were evaluated from thermogravimetry (TG) using Broido method. Differential scanning calorimetry (DSC) thermograms of these resins were also obtained. All the polyetherketones were tested for their antimicrobial properties against bacteria, fungi, and yeast. It was observed that most of the polyetherketones synthesized could be used as antibacterial and antifungal agents.     

香草醛缩2，4-二硝基苯腙的合成和抑菌性研究

利用香草醛和2,4-二硝基苯肼的缩合反应合成香草醛缩2，4-二硝基苯腙，利用红外、紫外光谱和元素分析进行了结构表征。采用琼脂扩散法，以金黄色葡萄球菌、短小芽孢杆菌、大肠杆菌、沙门氏菌为生物指标，研究了香草醛缩2，4-二硝基苯腙对4种菌种的抑制作用，结果表明，在一定的浓度范围内，目标产物对所受试菌种具有一定的抑制作用。     

Design,Synthesis, Antibacterial,Antifungal and Anticancer Evaluations of Novel β-Pinene Quaternary Ammonium Salts

β-pinene is a monoterpene isolated from turpentine oil and numerous other plants’ essential oils, which has a broad spectrum of biological activities. In the current work, six novel β-pinene quaternary ammonium (β-PQA) salts were synthesized and evaluated in vitro for their antifungal, antibacterial and anticancer activities. The in vitro assay results revealed that compounds 4a and 4b presented remarkable antimicrobial activity against the tested fungi and bacteria. In particular, compound 4a showed excellent activities against F. oxysporum f.sp. niveum, P. nicotianae var.nicotianae, R. solani, D. pinea and Fusicoccumaesculi, with EC₅₀ values of 4.50, 10.92, 9.45, 10.82 and 6.34 μg/mL, respectively. Moreover, compound 4a showed the best antibacterial action against E. coli, P. aeruginosa, S. aureus and B. subtilis, with MIC at 2.5, 0.625, 1.25 and 1.25 μg/mL, respectively. The anticancer activity results demonstrated that compounds 4a, 4b, 4c and 4f exhibited remarkable activity against HCT-116 and MCF-7 cell lines, with IC₅₀ values ranged from 1.10 to 25.54 μM. Notably, the compound 4c displayed the strongest cytotoxicity against HCT-116 and MCF-7 cell lines, with the IC₅₀ values of 1.10 and 2.46 μM, respectively. Furthermore, preliminary antimicrobial mechanistic studies revealed that compound 4a might cause mycelium abnormalities of microbial, cell membrane permeability changes and inhibition of the activity of ATP. Altogether, these findings open interesting perspectives to the application of β-PQA salts as a novel leading structure for the development of effective antimicrobial and anticancer agents.     

Synthesis,Surface and Antimicrobial Activities of Novel Cationic Gemini Surfactants

A series of novel cationic gemini surfactants [C_nH_2n+1–O–CH₂–CH(OH)–CH₂–N⁺(CH₃)₂–(CH₂)₂]₂·2Br^? [ 3a (n = 12), 3b (n = 14) and 3c (n = 16)] having a 2‐hydroxy‐1,3‐oxypropylene group [?CH₂–CH(OH)–CH₂–O–] in the hydrophobic chain have been synthesized and characterized. Their water solubility, surface activity, foaming properties, and antibacterial activity have been examined. The critical micelle concentration (CMC) values of the novel cationic gemini surfactants are one to two orders of magnitude smaller than those of the corresponding monomeric surfactants. Furthermore, the novel cationic gemini surfactants have better water solubility and surface activity than the comparable [C_nH_2n+1–N⁺(CH₃)₂–(CH₂)₂]₂·2Br^? (n‐4‐n) geminis. The novel cationic gemini surfactants 3a and 3b also exhibit good foaming properties and show good antibacterial and antifungal activities.     

有机-无机复合抗菌剂的制备及抗菌性能

依次将无机抗菌离子(锌离子)和有机抗菌离子(十四烷基三丁基季鏻盐)插入到蒙脱土中制备出有机-无机复合抗菌剂,其中锌和季鏻盐的含量分别为2.60%(质量分数)和22.31%(质量分数)。热重(TG)、X-射线衍射(XRD)分析结果表明,锌离子和季鏻盐确实交换到蒙脱土中,并且复合抗菌剂中有机物的热分解起始温度为220℃左右,具有较好的热稳定性。抗菌试验的结果表明,复合抗菌剂具有较好的抗菌性能,对S.aereus和E.coli的最小抑菌浓度(MIC)分别为100μg.mL-1和300μg.mL-1。将100mg复合抗菌剂在100mL蒸馏水中浸20d后,季鏻盐阳离子和Zn2 的释放量均很小,分别为4.831mg.L-1和1.896mg.L-1,表明复合抗菌剂具有良好的耐水性。     

Synthesis and Antimicrobial Activity of p-tetranitrocalix[4]arene Derivative

The present study demonstrates the synthesis and antimicrobial activity of the p-tetranitrocalix[4]arene (3). The microbial activity was determined against a variety of microorganisms, i.e., Gram-positive and Gram-negative bacterial strains such as Staphylococcus aureus ATCC 10231, Streptococcus viridans ATCC 12392, Escherichia coli ATCC 8739, as well as some fungal species including Aspergillus niger ATCC 16404, Aspergillus flavus ATCC 90906, and Candida albicans ATCC 32333. Kirby-Bauer well agar diffusion method was employed for the determination of antimicrobial activity. All the microorganisms were applied to a selective agar medium (Mueller Hinton Agar) for growth. It was observed that compound 3 is considerably effective against selected microorganisms. The MIC values were also evaluated. Thus, from the results it could be deduced that compound 3 may be a valuable addition to the therapeutic index.     

N,N-二甲基十四烷基对乙烯基苄基氯化铵的合成及抑菌性能研究

以对乙烯基苄基氯和N,N-二甲基十四烷基叔胺(14DMA)为原料,合成了含有乙烯基的低毒高效的新型抗菌剂N,N-二甲基十四烷基对乙烯基苄基氯化铵。通过单因素实验确定优化的合成条件为:反应温度40～60℃、对乙烯基苄基氯与14DMA摩尔比1∶1.2、反应时间3h、20mL石油醚作溶剂、0.01g铜作催化剂,在此条件下产物收率达82.57%。产物的结构通过IR、1 HNMR确证。采用抑菌圈法研究了产物对金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌的抑菌活性,结果表明其抑菌效果良好。     

含噻二唑环噻吩并[2,3-d]嘧啶类含氟衍生物的合成及抗肿瘤活性

通过2-氨基-3-氰基噻吩与三氟乙酸、三氯氧磷反应"一锅法"制得2-三氟甲基-4-氯噻吩并[2,3-d]嘧啶,收率为60%,再与2-氨基-5-(取代苄硫基)-1,3,4-噻二唑发生芳香族亲核取代反应合成10个含噻二唑环噻吩并[2,3-d]嘧啶类含氟衍生物,收率为64%~75%。目标化合物的结构经红外光谱、核磁共振氢谱、质谱与元素分析表征,并采用MTT法对其进行初步的体外抗肿瘤活性筛选。结果表明,化合物Ⅳc和Ⅳf对Hep G2和BGC-823细胞的抑制活性高于对照样吉非替尼。