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Xu Tang Zhongbo Wang Xinmin Zhong Xiaobin Wang Lijuan Chen Ming He 《Phosphorus, sulfur, and silicon and the related elements》2019,194(3):241-248
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. 相似文献
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A series of novel 1,3,4-thiadiazole derivatives based on benzisoselenazolone were synthesized and evaluated for their cytotoxicity in vitro against human liver cancer cell SSMC-7721,human breast cancer cell MCF-7 and human lung cancer cell A549 by CCK-8 assay.The results showed mat compounds 7e,7f,7h,7k,71 and 7m displayed good cytotoxicity against MCF-7 cell lines.Compound 71 exhibited the most potent antitumor activities among the tested compounds. 相似文献
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2-取代硫醚-5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑类化合物的合成、结构与体外抗癌活性 总被引:19,自引:0,他引:19
以天然产物没食子酸为原料经醚化、酯化、酰肼化、成盐、闭环、硫醚化六步反应合成了6个2-取代硫醚-5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑类衍生物, 釆用铟催化下水相合成目标化合物8, 具有反应条件温和, 合成收率高的特点; 用IR, 1H NMR, 13C NMR和元素分析对各化合物进行了表征及结构确证, 并用X射线单晶衍射法测定了化合物8a [2-(2-氯-5-吡啶甲基)硫醚-5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑]的晶体结构, 采用MTT法进行了新化合物抑制PC3和BGC-823癌细胞体外试验, 结果表明在5μmol•L-1浓度下化合物8e对PC3的抑制活性为55.71%. 化合物8b对BGC-823细胞抑制活性为66.21%. 相似文献
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Baolei Wang Hongxue Wang Hang Liu Lixia Xiong Na Yang Yan Zhang Zhengming Li 《中国化学快报》2020,31(3):739-745
A series of novel phenylpyrazole carboxylic acid derivatives containing fluorine moiety,i.e.,diamides 11,simple aryl-bearing amides 12 and acylthioureas 14 were successfully synthesized based on the key fluo ro-containing phe nylpyrazole acid intermediate.The new compounds were identified and confirmed by melting point,1H NMR,13C NMR and elemental analysis or HRMS.The bioassay results indicated that some of the compounds possessed excellent insecticidal activities towards oriental armyworm,diamondback moth and corn borer at low concentrations.For examples,compounds 11a,11e-g and 14b exhibited remarkable larvicidal activities with LC50 values of 0.13-0.39 mg/L and 0.0002-0.0014 mg/L against oriental armyworm and diamondback moth,respectively,were comparable with those of the control chlorantraniliprole.Particularly,lie were found superior to chlorantraniliprole in oriental armyworm tests(LC50:0.23 mg/L vs.0.26 mg/L);11a,lie,11f and 14c in diamondback moth tests with LC50 values of 0.0002 mg/L,0.0002 mg/L,0.0008 mg/L and 0.0005 mg/L,respectively,we re more effective than that of chlorantraniliprole.In addition,12 a also showed a promising insecticidal potential and development/optimization advantage.Compounds 11a,lle-g,12a,14b and 14c could be considered as possible new leading structures for further study.The SAR investigation indicated that the compounds with fluorine motif(e.g.,-F,-CF2H,-CF3)held apparently favorable insecticidal potentials,which provided useful guidance for further design/development of new phenylpyrazole-containing agrochemicals. 相似文献
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A convenient synthesis of the dodecanoyl thiosemicarbazide derivatives 3a, b has been achieved from the reaction of 2-benzamido-3-arylacryloylhydrazides 1a, b and lauroyl isothiocyanate (2). The thiosemicarbazide derivative 3a is used as precursor for synthesis of 1,2,4-triazole, 1,3,4-thiadiazole, and 1,3-benzothiazole derivatives. The antimicrobial activity of some of the synthesized compounds was tested. 相似文献
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Synthesis and fungicidal activity of novel 1,2,4-triazole derivatives containing a pyrimidine moiety
Wen-Neng Wu Yang-Ming Jiang Qiang- Fei Hai-Tang Du 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):1171-1175
AbstractA series of novel 1,2,4-triazole derivatives containing a pyrimidine moiety were synthesized and their fungicidal activities were evaluated. The preliminary biological test indicated that some of the target compounds exhibited moderate to good fungicidal activities against the tested plant pathogenic fungi compared with the commercial agent. Among them, compounds 9n and 9o exhibited excellent antifungal activity against Phompsis sp., with the half-maximal effective concentration (EC50) values of 25.4 and 31.6?μg/mL, which were even better than the commercial agent of Pyrimethanil (32.1?μg/mL). Meanwhile, compound 9o showed better fungicidal activities against B. dothidea and B. cinerea with 40.1 and 55.1?μg/mL, respectively, in comparison with that of commercial Pyrimethanil (57.6 and 62.8?μg/mL). 相似文献
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《Journal of Saudi Chemical Society》2022,26(2):101415
The backbone structure (1,3,4-thiadiazole sulfone derivatives containing amide moiety) of target compounds was determined by modification and optimization of the theoretical design based on commercial chemical carboxin, including molecular docking, scaffold hopping, ligand expansion, etc.In this paper, 23 target compounds were synthesized by the combination of theoretical design and chemical synthesis, and characterized by 1H NMR, 13C NMR and HR MS. Addtionally, the antibacterical bioassay showed that most target compounds performed excellent inhibition on Xanthomonas axonopodis pv. citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) in vitro. Meanwhile, molecular docking, molecular dynamics (MD) simulations, and studies on ligand/protein (carboxin/2FBW and 4n/2FBW) complex systems were displayed, and the interaction patterns of ligand/protein complex system were predicted by molecular docking. Besides, the ligand/protein complex system was subject to MD simulation. The analysis of molecular dynamics such as RMSD values suggested that compound/2FBW complexes were stable. MM/GBSA (Molecular mechanics generalized born surface area) dynamic binding affinity results revealed that the active residues (TYR58, HIS26, ARG43, SER39, etc.) played an essential part in the binding of the compound(s) to form a stable low-energy ligand/protein complex, while the MD trajectories demonstrated that the interactions of drugs with 2FBW affected the tertiary structure and increased the stability of protein. Besides, compound 4n also showed control efficacies (curative and protective) on Xoo in vivo, where the curative efficacy was 35.91% and the protective efficacy was 18.97%. In a word, this study showed that 1,3,4-thiadiazole sulfone derivatives containing amide moiety designed based on the structure of carboxin were promising agricultural antibacterial agents, featuring certain stability of binding affinity to proteins and carboxin. 相似文献
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2,5-Bihydrazino-1,3,4-thiadiazole (2) was synthesized by condensation of 2,5-bimercapto-1,3,4-thiadiazole (1) with hydrazine hydrate, and compound 2 reacted with acyl chloride to give 2,5-biacylhydrazino-1,3,4-thiadiazole derivatives (3a–3e). Ring closure of compounds 3a–3e was achieved with POCl3 as the cyclization agent giving 3,6-bisubstituted phenyl-bi-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives (4a–4e), respectively. The novel compounds were identified by elemental analysis, and by infrared (IR), 1H-nuclear magnetic resonance
(NMR), and mass (MS) spectrometry. The mechanism of the cyclization is also discussed.
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Translated from Organic Chemistry, 2006, 26(12): 1720–1722 [译自: 有机化学] 相似文献
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以芹菜素为起始原料,在C-5、C-6、C-7、C-4′位置上引入甲基、苄基、乙酰基、对甲苯磺酰基、三异丙基硅烷基等多种单元结构基团,合成了16个芹菜素衍生物,采用CCK-8的方法考察了所合成化合物对人肝癌细胞(Hep3β)、人结肠癌细胞(LOVO)、人肺癌细胞(A549)的抑制作用。结果显示,经过化学修饰后的部分化合物比芹菜素有更强的抗肿瘤活性,其中化合物13对人肺癌细胞(A549)的抑制率超过了顺铂,值得进一步探讨和研究。 相似文献
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V. N. Yarovenko A. V. Shirokov I. V. Zavarzin O. N. Krupinova A. V. Ignatenko M. M. Krayushkin 《Chemistry of Heterocyclic Compounds》2003,39(12):1633-1639
We have developed a method for obtaining derivatives of 4,5-dihydro-1,3,4-thiadiazole-2-carboxamide by acylation of hydrazones of oxamic acid thiohydrazides. Oxidation of the dihydrothiadiazole ring of the indicated products by hydrogen peroxide leads to formation of 2-carbamoyl-4,5-dihydro-1,3,4-thiadiazole 1-oxides. 相似文献
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《Journal of Coordination Chemistry》2012,65(16-18):2814-2830
AbstractCo(II), Ni(II), and Cu(II) complexes of 2-Amino-5-ethyl-1,3,4-thiadiazole (AET) and 2-Amino-5-(ethylthio)-1,3,4-thiadiazole (AEST) have been synthesized and characterized based on elemental analysis, magnetic susceptibility, infrared (4000–400 cm?1), mass spectrometry (ESI and MALDI), UV–Vis (200–1100 nm) and thermal analysis (TGA/DTA). Molar conductance measurements proved that [M(L)2(H2O)2]Cl2·H2O are electrolytic complexes where M represents Co, Ni, and Cu divalent metal ions. The geometrical isomerism of [M(L)2(H2O)2]2+ ions were investigated by DFT-B3LYP calculations incorporated in Gaussian09 package; it favored the all trans isomers due to having the lowest energy points on the potential energy surface. The outcome of DFT-B3LYP quantum mechanical calculations using 6-31G(d) basis set favor six-coordinate sites via a bidentate ligand through exo amino and adjacent endo thiadiazole nitrogen (N3) donors. These results were consistent with magnetic measurements combined with infrared and UV–Vis spectral interpretations. The predicted metal–ligand binding energies from B3LYP/6-31G(d) calculations follow the trend Cu2+>Ni2+>Co2+, in agreement with the Irving–Williams series. Both AET and AEST ligands and the synthesized complexes were screened for their antibacterial activity and the outcome was high antimicrobial activity of the complexes compared to the free ligands against one or more microbial species and in some cases (copper complexes) higher activity than standard drugs. 相似文献
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Reaction of 2,5-dimercapto-1,3,4-thiadiazole with ammonia or pyridine gives monoammonium or monopyridinium slats, and the reaction with hydrazine hydrate gives both mono- and dihydrazine salts, which was confirmed by alkylation of the salts obtained. Difference in the chemical shifts of the SCH2R groups was found in the1H NMR spectra of the mono- and dialkyl-substituted 2,5-dimercapto-1,3,4-thiadiazoles.Institute of Chemistry, Vilnius LT-2600, LithuaniaTranslated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 682–687, May, 2000. 相似文献
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《Arabian Journal of Chemistry》2019,12(7):1501-1506
A novel and fairly efficient chemoselective one-pot method has been developed for the synthesis of both 2-phenylamino-5-alkylthio-1,3,4-thiadiazole and bis-(2-phenylamino-5-alkylthio-)1,3,4-thiadiazole derivatives from phenylthiosemicarbazide and CS2. 相似文献
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2,5-二取代-1,3,4-噻二唑衍生物的一锅法合成、结构表征及生物活性研究 总被引:4,自引:0,他引:4
采用超声波辐射与相转移催化联用技术, 一锅法合成出了8个新的2-(1-萘乙酰氨基)-5-芳氨甲基-1,3,4-噻二唑化合物, 这种合成方法具有反应条件温和、反应时间较短、产率较高等特点. 新化合物的结构利用IR, 1H NMR, 13C NMR, 1D NOE, MS和元素分析进行了表征. 人环氧酶-2 (COX-2)活性抑制实验结果表明, 目标化合物5f对COX-2具有很强的抑制活性, 抑制率高达95.59%; 化合物5g对COX-2也具有一定的抑制活性. 目标化合物无抗惊厥活性. 相似文献
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In the work discussed in this paper, a series of novel benzaldehyde derivatives containing 1,3,4-thiadiazole were prepared in high yield from 4-fluorobenzaldehyde and 2-amino-5-substituted-1,3,4-thiadiazole. The products were characterized by determination of melting point, elemental analysis, and UV–visible, IR, 1H NMR, and 13C NMR spectroscopy. The fluorescence properties of the compounds were also studied by recording their fluorescence emission spectra. 相似文献