N-[1-(取代苯基)乙基]-2-羟基苯甲酰肼的合成、表征及抑菌活性

依据邻羟基二苯醚及芳香肼类化合物的抗菌特性, 以邻羟苯基为分子核心, 酰肼键为桥基, 设计合成了7种未见报道的N-(取代苯基)乙基-2-羟基苯甲酰肼类化合物. 以水杨酸甲酯为原料, 经肼解反应后与取代苯乙酮缩合, 再与硼氢化钠反应制得目标化合物, 化合物结构经IR, ¹H NMR和元素分析等证实. 抗菌活性测试结果表明, 该类化合物对不同菌株的抑菌活性具有明显的选择性和特异性. 当质量浓度为1×10^-4 g/mL时, 化合物3b和3e对大肠杆菌和白色念珠菌的抑菌率高达100%, 有极强的抑菌活性; 所有化合物对金黄色葡萄球菌的抑菌率均大于70%, 有一定的抑菌活性. 构效关系分析结果表明, 苯基中引入Cl或Br等卤原子能显著增强化合物的抑菌活性, 而引入-NO₂及-CH₃基团则会降低其抑菌活性.     

5-溴-2-羟基苯甲酰基取代芳醛腙的合成、表征及抑菌活性

以水杨酸甲酯为原料,先经溴化反应制得5-溴水杨酸甲酯,再经肼解反应制得5-溴-2-羟基苯甲酰肼,再与取代芳香醛缩合反应,制得7种5-溴-2-羟基苯甲酰基取代芳醛腙,其中3种为新化合物. 化合物的结构经IR、1H NMR、MS与元素分析测试技术表征确证. 抑菌测试表明,该类化合物对不同菌株的抑菌活性具有明显的选择性;在质量浓度为0.05%时,上述化合物对白色念珠菌、枯草芽孢杆菌的抑菌率高达100%,具有强抑菌活性,是一类极具潜力的抗真菌、抗革兰氏阳性菌的化合物. 5-溴-2-羟基苯基-3′,5′-二溴-2-羟基苯甲醛腙的抗菌活性接近广谱高效杀菌剂三氯生. 构效分析表明,化合物的抑菌活性与Ar环及其取代基性质有关,引入呋喃环、Ar环邻、对位引入-OH、-OCH_3等供电基容易导致化合物抑菌活性降低,Ar环的间位引入Cl、Br等卤素原子能够提高化合物的抑菌活性.     

N-取代苯基-卤代邻羟基苄胺的合成、表征及抑菌活性

通过卤代水杨醛与取代芳胺缩合、NaBH4还原, 合成了15种N-取代苯基-卤代邻羟基苄胺化合物, 其中14种未见报道. 化合物的结构经IR, 1H NMR, MS与元素分析表征确证. 抑菌测试表明, 在质量浓度为0.05%时, 化合物对白色念珠菌的抑菌率高达100%, 具有强抑菌活性, 对金黄色葡萄球菌、大肠杆菌有一定的抑菌活性. 该类化合物对不同菌株的抑菌活性具有明显的选择性和特异性, 是一类极具潜力的抗真菌化合物. 构效分析表明, 胺基苯环上取代基的类型对化合物抑菌活性有重要影响, 引入F, Cl等卤原子, 能显著增强化合物的抑菌活性, 而引入NO2, OCH3等强吸、供电基团, 能显著降低其抑菌活性; 邻羟基苯环上引入卤原子的类型和数量对化合物抑菌活性有一定影响, 5-溴代化合物比5-氯代化合物、3,5-二溴代化合物对大肠杆菌的抑菌活性更高.     

Two New Metabolites,Epoxydine A and B,from Phoma sp.

The new compounds, epoxydines A and B ( 1 and 2 , resp.), along with the known and related metabolites, 3 – 6 , were isolated from the fungal endophyte Phoma sp. The structures of the new compounds were elucidated by detailed spectroscopic analysis, and the relative configuration of 1 was confirmed by ROESY experiments. Preliminary studies indicated that compounds 2 – 5 possess good antibacterial, antifungal, and algicidal properties. Similarly, compound 1 showed antifungal and algicidal, and compound 6 antibacterial and algicidal properties.     

Preparation of Some Thiazolyl Hydrazone Derivatives and Evaluation of Their Antibacterial Activities

The increasing clinical importance of drug-resistant fungal and bacterial pathogens has provided additional urgency to microbiological research and to the development of new antibacterial compounds. For this purpose, new tert-butyl [1-aryl/alkyl-2[(4-aryl-2-thiazolyl)hydrazono]ethyl]carbamate derivatives were synthesized and evaluated for antibacterial activity. The reaction of Boc-L-phenylalaninal, Boc-D-phenylalaninal, Boc-L-leucinal, and Boc-L-tryptophanal with thiosemicarbazide yielded the thiosemicarbazones, which furnished the title compounds on reaction with phenacyl bromides. The new compounds were screened for antibacterial activity. The results from the bioassay tests show that some of the compounds have notable activity against Gram-positive bacteria.     

3-杂环硫亚甲基头孢菌素衍生物的半合成及抗菌活性研究

通过取代噁二唑硫酮、噻二唑硫酮及三唑硫酮分别和头孢菌素母体7-ACA反应,制得14种7-氨基-3-杂环硫亚甲基头孢菌素新母体2a-2n,用1-芳基-5-甲基-1H-1,2,3-三唑-4-甲酰氯与头孢菌素新母体缩合,制得2种新的7β-(1-芳基-5-甲基-1H-1,2,3-三唑-4-甲酰胺基)-3-(2-取代1,3,4-bI二唑-5-硫亚甲基)头孢菌素4c,4d.新化合物结构经元素分析、IR、¹HNMR及FAB-MS确认.初步体外抗菌结果表明,新母体化合物2对革兰氏阳性菌有抑制活性且在相同浓度下比7-ACA强20倍,而头孢菌素4c,4d对革兰氏阳性和阴性菌都有显著抑制活性.     

QSAR analysis of 1,3-diaryl-2-propen-1-ones and their indole analogs for designing potent antibacterial agents

A series of 1,3-diaryl-2-propen-1-ones and their indole analogs were synthesized and evaluated for antibacterial activity. Structures of newly synthesized compounds were confirmed by physicochemical, spectral and elemental analysis. All the compounds were screened for their antibacterial activities against four different bacterial strains. The QSAR studies were performed using Vlife MDS 3.5 software. QSAR equation revealed that selected electronic, steric and lipophilic parameters have good correlation with antibacterial activity. Best equations were selected on basis of the correlation coefficient (r ²) and the predictable ability of the equations. The present findings suggest that the 1,3-diaryl-2-propen-1-ones framework is an attractive template for structure optimization to achieve higher potency, lower toxicity, and a wider spectrum of antibacterial activity.     

手性2-甲氧羰基-4-氟苯基-1,5-苯并硫氮杂卓的不对称合成及抑真菌活性

以(R)/(S)-4-苄基-2-噁唑烷酮为手性助剂,采用不对称合成方法制备了18个具有光学活性的2-甲氧羰基-4-氟苯基-1,5-苯并硫氮杂卓类化合物9a~9i和14a~14i,经HPLC分析e.e.值较为理想;通过核磁共振谱、红外光谱和高分辨质谱表征了其结构,通过单晶X射线衍射法确定化合物9h的相对构型;用抑菌圈法测试了目标化合物对新生隐球菌的抑菌活性.研究结果表明,由S型手性助剂诱导不对称合成的杂卓对新生隐球菌的抑制作用普遍高于由R型手性助剂诱导合成的杂卓及外消旋体.测试了抑菌活性较好的化合物14a~14f的最小抑菌浓度(MIC)和最小杀菌浓度(MFC),发现其对新生隐球菌的MIC和MFC均低于抗真菌药物氟康唑.     

海洋放线菌S592次级代谢产物及其体外抑菌活性研究

对海洋放线菌S592的次级代谢产物以及体外抑菌活性进行研究.将菌株S592进行大量发酵,采用色谱方法对菌株发酵产物进行分离纯化,通过波谱技术对所获单体化合物进行结构鉴定,并测定化合物的体外抑菌活性.从海洋放线菌S592中分离得到6个化合物,含2个螺环抗生素lobophorin类化合物,1个环肽类化合物,2个苯甲酰胺类化...     

Structural modification of sanguinarine and chelerythrine and their antibacterial activity

In this study, five derivatives of sanguinarine (1) and chelerythrine (2) were prepared, with 1 and 2 as starting materials, by reduction, oxidation and nucleophilic addition to the iminium bond C=N+. The structures of all compounds were elucidated on account of their MS, 1H-NMR and 13C-NMR data. The antibacterial activities of all compounds were screened, using Staphylococcus aureus, Escherichia coli, Aeromonas hydrophila and Pasteurella multocida as test bacteria. The minimum bacteriostatic concentration and minimum bactericidal concentration of the active compounds were determined by the turbidity method. The structure-activity relationships of 1 and 2 were discussed. The results showed that 1, 2 and their pseudoalcoholates were found to be potent inhibitors to S. aureus, E. coli and A. hydrophila, while the other derivatives were found to be inactive. The pseudoalcoholates might be the prodrugs of 1 and 2. The iminium bond in the molecules of 1 or 2 was the determinant for antibacterial activity, and the substituents at the 7 and 8 positions influenced the antibacterial activities of 1 and 2 against different bacteria.     

Three antibacterial naphthoquinone analogues from cultured mycobiont of lichen Astrothelium sp.

<正>A new naphthoquinone compound named 7-hydroxyl-8-methoxyltrypethelone 3 together with two known compounds trypethelone 1 and trypethelone methyl ether 2 was isolated from cultured mycobiont of Astrothelium sp.The structures were elucidated by 1D and 2D NMR spectroscopic analysis as well as comparison with those reported in literatures.Compound 1 displayed significant antibacterial activity against Bacillus subtilis(ATCC 6633),and showed modest antibacterial activity against Staphylococcus aureus col(MRSA)(CGMCC 1.2465),while compounds 2 and 3 showed modest antibacterial activity against Enterococcus faecalis 850E(CGMCC 1.2135) and S.aureus col(MRSA)(CGMCC 1.2465).     

新型苯并咪唑衍生物的合成及生物活性研究

以取代苯酚为原料,合成8个新型的2-苯氧甲基苯并咪唑类化合物,通过1H-NMR和HRMS确认其结构。MTT法测试其抗肿瘤活性,实验结果表明,大部分化合物具有较好的广谱抗肿瘤效果,其中化合物2h对大多数肿瘤细胞株的IC50值均达到了低微摩尔水平,对人胰腺癌(BxPC-3)的IC50达到3.6μM。试管二倍稀释法测试其抗菌活性,实验结果表明,目标化合物显示出抗菌活性,化合物2a对粪肠球菌和金黄色葡萄球菌的MIC达到16μg/mL。     

Synthesis, antibacterial and antifungal activity of some derivatives of 2-phenyl-chromen-4-one

Some derivatives of 2-phenyl-chromen-4-one (flavone ring) have been synthesized and tested for antibacterial and antifungal activities along with their chalcone precursors against four human pathogenic bacteria and five plant mould fungi. The structures of the synthesized compounds were elucidated by UV, IR and¹H NMR spectroscopic techniques, and elemental analysis. The antibacterial and antifungal screens of the synthesized compounds were performed in vitro by the filter paper disc diffusion method and the poisoned food technique.     

Synthesis, spectral studies and antibacterial activity of novel macrocyclic Co(II) compounds

Ten novel macrocyclic Co(II) compounds have been synthesized by treating four N(4) and six N(2)O(2) donor macrocycles with cobalt chloride in methanol. These compounds were characterized by elemental, IR, (1)H, (13)C NMR, mass, electronic spectral analysis, molar conductance and magnetic susceptibility measurements. Thermal behavior of these compounds has been studied by the thermogravimetric analysis. An octahedral geometry has been proposed for all of these complexes. All the macrocycles and macrocyclic Co(II) compounds along with existing antibacterial drugs were screened for antibacterial activity against Gram +ve and Gram -ve bacteria. All these compounds were found to be more active when compared to streptomycin and ampicillin.     

Synthesis and Antibacterial Activities of 1,4-Disubstituted Phenyl-5-(halo-2-hydroxyphenyl)imino-1,2,3-triazole

According to the superposition principle of reinforcement of biological activities, 24 novel 1,4- disubstituted phenyl-5-(halo-2-hydroxyphenyl)imino-1,2,3-triazoles was synthesized and characterized by 1H NMR, ¹³C NMR, elemental analysis and IR. All the target compounds were screened for their antibacterial potential in vitro against Monilia albican, Escherichia coli and Staphylococcus aureus. It was shown that all the compounds possessed efficient antibacterial activities at a concentration of 0.1 mg/mL, even at a concentration of 0.01 mg/mL, some of the compounds still exhibited antibacterial activities against Escherichia coli and Monilia albican. At last, the structure- activity relationship was discussed based on the antibacterial results.     

5-溴-邻羟苯基芳基取代酰腙的合成、表征及抑菌活性研究

以水杨酸甲酯为原料,先经溴化反应制得5-溴水杨酸甲酯,再经肼解反应制得5-溴-2-羟基苯甲酰肼,再与取代芳香醛缩合反应,制得7种5-溴-2-羟基苯甲酰基取代芳醛腙,其中3种为新化合物。 化合物的结构经IR、¹H NMR、MS与元素分析测试技术表征确证。 抑菌测试表明,该类化合物对不同菌株的抑菌活性具有明显的选择性;在质量浓度为0.05%时,上述化合物对白色念珠菌、枯草芽孢杆菌的抑菌率高达100%,具有强抑菌活性,是一类极具潜力的抗真菌、抗革兰氏阳性菌的化合物。 5-溴-2-羟基苯基-3′,5′-二溴-2-羟基苯甲醛腙的抗菌活性接近广谱高效杀菌剂三氯生。 构效分析表明,化合物的抑菌活性与Ar环及其取代基性质有关,引入呋喃环、Ar环邻、对位引入-OH、-OCH₃等供电基容易导致化合物抑菌活性降低,Ar环的间位引入Cl、Br等卤素原子能够提高化合物的抑菌活性。     

Novel azo dyes derived from 8-methyl-4-hydroxyl-2-quinolone：Synthesis, UV-vis studies and biological activity

In this study, N,N'-di-(2-methylphenyl)malonamide was synthesized and reacted with polyphosphoric acid to afford 8-methyl-4-hydroxyl-2-quinolone. Eight novel azo disperse dyes were then synthesized by linking diazotized p-substituted aniline derivatives with 8-methyl-4-hydroxyl-2-quinolone. The solvatochromism of these azo dyes in various solvents was evaluated. All the compounds were then evaluated for their antibacterial activity against four bacteria, namely, Bacillus subtilis, Micrococcus luteus, Salmonella enterica, and Pseudomonas aeruginosa. The results showed that some of these compounds have high levels of antibacterial activity.     

3-取代硫基-5-(2-羟基苯基)-4H-1,2,4-三唑类化合物抑菌活性的定量构效关系和结构修饰的理论研究

用DFT-B3LYP 方法, 在基组6-31G 水平, 对24 种3-取代硫基-5-(2-羟基苯基)-4H-1,2,4-三唑类化合物分子进行几何优化, 并计算了E_HOMO, E_LUMO, E_NHOMO, E_NLUMO, Q_C1～Q_C8, Q_N1～Q_N3, Q_O, Q_S和ΔE₁, ΔE₂, ΣQ 等量子化学描述符(q_c). 通过最佳变量子集回归建立13 种上述化合物对大肠杆菌、白色念珠菌、金黄色葡萄球菌等抑菌活性(A_J: A_e, A_m 和A_s) 的QSAR 模型. 对于大肠杆菌的A_e 模型的相关系数(R²)和逐一剔除法交叉验证系数R_cv² 依次为0.930 和0.871, 相应白色念珠菌A_m 模型为0.926 和0.869, A_s 模型为0.781 和0.572. 通过R_adj², F, R_cv², VIF, AIC, FIT 等检验, 上述模型具有令人满意的稳健性和预测能力. 结果显示ΔE₁ 和ΣQ 直接影响这些化合物的生物活性: ΣQ 增大, 其抑菌活性增强; ΔE₁ 越高, A_J 下降. 据此提出三唑类化合物分子可能的抑菌机理. 由此发现, 在三唑类化合物分子的R 中合适部位选用吸电子能力较强的取代基团进行结构修饰, 有利于提高被修饰后分子的抑菌活性. 根据对R 进行结构修饰(共提出11 种化合物), 得出4 种抑菌活性均超出100%的三唑类化合物(质量分数为0.01%), 希望将来得到生物实验的证实.     

3-取代-1-(5-芳基-1,3,4-噻二唑-2-基)-1H-吡唑-4-甲醛的合成、晶体结构及抑菌活性

以2-氨基-5-取代-1,3,4-噻二唑为起始原料,设计合成16个含1,3,4-噻二唑取代基的中间体4a~4p,进而使其在POCl₃及DMF作用下反应得到16个3-取代-1-(5-芳基-1,3,4-噻二唑-2-基)-1H-吡唑-4-甲醛化合物5a~5p,所合成的32个化合物均为新化合物。 采用溶液结晶法获得化合物5a晶体,通过X射线单晶衍射测得该晶体属于三斜晶系,P-1空间群。 借助 IR、¹H NMR、元素分析等技术手段对合成的所有化合物结构进行了表征。 利用微量稀释法测试了化合物5a~5p的抑菌活性,结果表明,部分化合物对金黄色葡萄球菌具有抑制作用,在相同条件下化合物5h的抑菌活性最好,抑菌率达到65.30%。     

One-pot,three-component synthesis and in vitro antibacterial evaluation of novel 3-amino-N-benzyl-1-aryl-1H-benzo[f]chromene-2-carboxamide derivatives

A series of novel 3-amino-N-benzyl-1-aryl-1H-benzo[f]chromene-2-carboxamides have been synthesized by the reaction of N-benzyl-2-cyanoacetamide with 2-naphthol and aromatic aldehydes in the presence of piperidine as a base. The chemical structures of all the compounds were confirmed by spectroscopic methods as well as elemental analysis. In addition, the antibacterial activities of some target compounds against Gram-negative and Gram-positive bacteria in vitro were determined. Among these compounds, 4b, 4c, 4h and 4i exhibited antibacterial effects. The advantages of the present work reaction are clean reaction, metal-free transition, environmentally friendly approach to prepare different benzo[f]chromene-2-carboxamide derivatives, good yields, low cost, readily available starting materials and in addition does not need cumbersome procedure.