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1.
以31个分子结构与生物活性(-lgIC50)已知的流感病毒神经氨酸酶抑制剂为训练集,选用16个分子的理化描述子,包括分子的形状,静电作用能和范德华作用能以及疏水描述子,用二维定量构效关系(2D-QSAR)方法建立了预测模型。计算中使用偏最小二乘(PLS)和主成分分析(PCA)降低变量维数,减少噪音干扰。用交叉验证法(leave one out,LOO)检验了预测模型的可信性,并用一个由4个抑制剂组成的测试集进一步验证预测模型的预测能力,证实了QSAR预测模型有较好的预测能力。神经氨酸酶抑制剂的QSAR预测模型的建立为抗流感药物的设计和改进提供了有用的研究工具。 相似文献
2.
Tu S Xu LH Ye LY Wang X Sha Y Xiao ZY 《Journal of agricultural and food chemistry》2008,56(13):5247-5253
Nineteen novel indene-substituted oxime ether strobilurins, which used an indene group to stabilize the ( E)-styryl group in SYP-Z071 (an unsaturated oxime strobilurin fungicide under development by the Shenyang Research Institute of Chemical Industry), were designed and synthesized. The biological assay results showed that all compounds possessed good or excellent fungicidal activities. It was found that most of the compounds showed higher fungicidal activities against Pyricularia oryzae, Phytophthora infestans, Erysiphe graminis, and Colletotrichum lagenarium than SYP-Z071 at the tested concentration. The biological assay results also indicated that most of the compounds exhibited higher in vivo fungicidal activities against cucumber Pseudoperonospora cubensis and C. lagenarium than the commercial fungicides trifloxystrobin and kresoxim-methyl at a concentration of 6.25 mg/L. Furthermore, it was found that alpha-(methoxyimino)- N-methylphenylacetamide oxime ethers 6m- s exhibited a broad spectrum and remarkably higher activities against all tested fungi. Especially, the 6-methylindene-substituted compound 6p was identified as the most promising candidate for further study. 相似文献
3.
Twenty-two new benzoylphenylureas containing isoxazoline and the isoxazole group were designed and synthesized, and their structures were characterized by (1)H NMR and elemental analysis (or HRMS). The larvicidal activities against Oriental armyworm, mosquito, and diamondback moth of the new compounds were evaluated. Compounds I-1 and III-1 showed nearly the same level of insecticidal activity against Oriental armyworm as commercial insecticide Flucycloxuron and surprisingly exhibited much higher larvicidal activities against diamondback moth than Flucycloxuron. 相似文献
4.
Zhu YQ Wu C Li HB Zou XM Si XK Hu FZ Yang HZ 《Journal of agricultural and food chemistry》2007,55(4):1364-1369
A series of pyrazolo[5,1-d][1,2,3,5]tetrazin-4(3H)one derivatives were designed, synthesized, and evaluated for their herbicidal activities where some of these compounds provided >80% control of Brassica campestris at 10 microg/mL. Quantitative structure-activity relationship studies were performed on these compounds using physicochemical parameters (electronic, Verloop, or hydrophobic) as independent parameters and herbicidal activity as a dependent parameter, where herbicidal activity correlated best (r > 0.8) with physicochemical parameters in this set of molecules. The herbicidal activity against B. campestris was mainly affected by the molar refractivity (MR) for R1, Taft (Eso) for R2 or R6, Verloop (Lm) for R3 or R5, and electronic parameters (Hammett's constants) for R4. The optimal MR for herbicidal activity is 0.95. The herbicidal activity against Echinochloa crus-galli was mainly related with the substituents' hydrophobic parameter. The optimal pi parameters for R1 and R4 for herbicidal activity are 0.72 and 0.68, respectively. In general, these compounds showed greater herbicidal activity toward B. campestris than E. crus-galli. 相似文献
5.
Enormous numbers of synthetic fluorine-containing compounds have been widely used in a variety of fields, especially in drug and pesticide design. To find novel insect growth regulators, a series of benzoylphenylureas with fluorinated substituents were designed and synthesized. The results of larvicidal activities of those novel fluoro-substituted benzoylphenylureas against oriental armyworm and mosquito revealed that most compounds exhibited excellent activities. It is worth mentioning that compounds 3 and 6 exhibited higher activities against oriental armyworm and mosquito than commercial Hexaflumuron. It can be further seen that the insecticidal activities would increase significantly by introducing fluorinated substituents into the structure of the designed benzoylphenylureas. 相似文献
6.
Liu Z Lei Q Li Y Xiong L Song H Wang Q 《Journal of agricultural and food chemistry》2011,59(23):12543-12549
A series of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety was designed and synthesized via the key intermediate 3-(2,4,6-trimethyl)-2-oxo-1-oxaspiro[4.4]-decyl-3-en-4-ol. The target compounds were identified by (1)H NMR and elemental analysis or high-resolution mass spectrum (HRMS). The results of bioassays indicated that most of the target compounds possessed excellent acaricidal activities against carmine spider mite larvae and eggs. Especially, diisopropylamino oxalyl compound 7g and piperidine oxalyl compound 7h were 1.4- and 2.3-fold as high as the activities of commercial Spiromesifen, respectively, against spider mite eggs. Moreover, most of the target compounds exhibited insecticidal activities against Lepidoptera pest. Interestingly, compounds containing alkylamino-substituted oxalyl moiety showed obvious selectivity between spider mite larvae and eggs because the activities against spider mite eggs of 7g and 7h were 25-fold those against spider mite larvae, whereas Spiromesifen had no significant differences in these activities. This meant that the introduction of an oxalyl moiety to spirocyclic tetronic acid might lead to novel biological activity characteristics. 相似文献
7.
Dai H Li YQ Du D Qin X Zhang X Yu HB Fang JX 《Journal of agricultural and food chemistry》2008,56(22):10805-10810
A series of novel pyrazole oxime derivatives containing a 2-chloro-5-thiazolyl moiety were synthesized. Their structures were confirmed by (1)H NMR, (13)C NMR, and elemental analysis. The preliminary bioassays showed that all of the title compounds had low acaricidal activity against Tetranychus cinnabarinus . However, most of them exhibited excellent insecticidal activity against Aphis medicagini at the dosage of 0.5 mg/mL, and some compounds still showed good insecticidal activity against A. medicagini even at the dosage of 0.2 mg/mL. Meanwhile, some title compounds displayed fungicidal and plant growth regulatory activities. 相似文献
8.
Zheng Z Wang J Zhang D Guan X Gao S Chen Z Zou X 《Journal of agricultural and food chemistry》2011,59(4):1171-1177
A series of novel monohalovinylated pyrethroids are designed and synthesized to replace one halo atom with a hydrogen atom on the double bond of dihalopyrethroids. Bioassays indicate that some of the synthesized compounds, such as 3j and 1j, exhibit high insecticidal activities against mosquitoes ( Culex pipiens pallens ), oriental armyworms ( Mythimna separata ), alfalfa aphids ( Aphis medicagini ), and carmine spider mites ( Tetranychus cinnabarinus ). Photolytic results of E-cis-1j suggest that monohalovinylated pyrethroids are photodegraded more easily than compound 12. 相似文献
9.
Macías FA Marín D Oliveros-Bastidas A Castellano D Simonet AM Molinillo JM 《Journal of agricultural and food chemistry》2006,54(4):1040-1048
Avena fatua L. (wild oat) and Lolium rigidum Gaud. (rigid ryegrass) are highly problematic weeds affecting a wide variety of cereal crops worldwide. The fact that both of these weeds have developed resistance to several herbicide groups made them optimal candidates as target organisms for ongoing research about the potential application of allelochemicals and analogue compounds as natural herbicide models. Benzoxazinones, a family of natural allelochemicals present in corn, wheat, and rye, including 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one and 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one, together with some degradation products, found in crop soils as well as in other systems, and some synthetic analogues of them were tested on wild oat and rigid ryegrass seeds; the results were statistically treated, and some structure-activity relationships, useful in further development of natural herbicide models, were elucidated. The most active compounds were the synthetic benzoxazinone 2-acetoxy-(2H)-1,4-benzoxazin-3(4H)-one and the degradation product 2-aminophenoxazin-3-one, with highly significant inhibition on the development of both weeds. The ecological role of these compounds is discussed by considering both degradability and phytotoxicity. The bioactivity of aminophenoxazines has been correlated by their aqueous solubility-lipophilicity predicted by means of computational methods. 相似文献
10.
Macías FA Marín D Oliveros-Bastidas A Castellano D Simonet AM Molinillo JM 《Journal of agricultural and food chemistry》2005,53(3):538-548
Benzoxazinones 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA) have been considered key compounds for understanding allelopathic phenomena in Gramineae crop plants such as corn (Zea mays L.), wheat (Triticum aestivum L.), and rye (Secale cereale L.). The degradation processes in the environment observed for these compounds, in which soil microbes are directly involved, could affect potential allelopathic activity of these plants. We present in this work a complete structure-activity relationships study based on the phytotoxic effects observed for DIMBOA, DIBOA, and their main degradation products, in addition to several synthetic analogues of them. Their effects were evaluated on standard target species (STS), which include Triticum aestivum L. (wheat) and Allium cepa L. (onion) as monocots and Lepidium sativum L. (cress), Lactuca sativa L. (lettuce), and Lycopersicon esculentum Will. (tomato) as dicots. This permitted us to elucidate their ecological role and to propose new herbicide models based on their structures. The best phytotoxicity results were shown by the degradation chemical 2-aminophenoxazin-3-one (APO) and several 2-deoxy derivatives of natural benzoxazinones, including 4-acetoxy-(2H)-1,4-benzoxazin-3(4H)-one (ABOA), 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIBOA), and 4-hydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIMBOA). They showed high inhibitory activity over almost all species growth. The fact that APO is a degradation product from DIBOA with high phytotoxicity and stability makes it possible to assign an important ecological role regarding plant defense mechanisms. 2-Deoxy derivatives of natural benzoxazinones display a wide range of activities that allow proposing them as new leads for natural herbicide models with a 1,4-benzoxazine skeleton. 相似文献
11.
Peng H Wang T Xie P Chen T He HW Wan J 《Journal of agricultural and food chemistry》2007,55(5):1871-1880
Molecular docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) studies on the title compounds were performed to explore the possible inhibitory mechanism. To determine the probable binding conformations of the title phosphonate derivatives, the most potent compound 12 was chosen as a standard template and docked into the active site of PDHc E1. On the basis of the binding conformations, highly predictive 3D-QSAR models were developed with q2 values of 0.872 and 0.873 for comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA), respectively. The predictive abilities of these models were validated by using a set of compounds that were not included in the training set. Both the CoMFA and the CoMSIA field distributions are in good agreement with the spatial and electronic structural characteristics of the binding groove of PDHc E1 selected in this work. Mapping the 3D-QSAR models to the active site of PDHc E1 provides new insight into the protein-inhibitor interaction mechanism, which is most likely valuable and applicable for designing highly active compounds in the future. 相似文献
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13.
Wang J Tan H Li Y Ma Y Li Z Guddat LW 《Journal of agricultural and food chemistry》2011,59(18):9892-9900
Acetohydroxyacid synthase (AHAS) catalyzes the first common step in the biosynthesis of the branched-chain amino acids. As a result of its metabolic importance in plants, it is a target for many commercial herbicides. Virtual screening analysis inspired the evaluation of 19 commercially available isatin analogues and 13 newly synthesized isatin derivatives as novel AHAS inhibitors and for their herbicidal activity. The best compound demonstrated 95% inhibition of the activity of Arabidopsis thaliana AHAS at a concentration of 100 mg L(-1), whereas the herbicidal activities of three compounds reached 50% inhibition at a concentration of 10 mg L(-1) using the rape root growth test. CoMFA contour models were established to understand the structure-activity relationships for this class of AHAS inhibitor. The compounds were docked to the active site cavity of A. thaliana AHAS using FlexX, and the dominant binding mode was consistent with frontier molecular orbital from DFT calculations. This is the first comprehensive study of isatin derivatives as AHAS inhibitors and provides a valuable starting point for the design of new herbicides. 相似文献
14.
Caballero J Saavedra M Fernández M González-Nilo FD 《Journal of agricultural and food chemistry》2007,55(20):8101-8104
Three-dimensional quantitative structure-activity relationship (3D-QSAR) studies were carried out on a series of 38 rubiscolins as delta opioid peptides using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA). Quantitative information on structure-activity relationships is provided for further rational development and direction of selective synthesis. All models were carried out over a training set including 30 peptides. The best CoMFA model included electrostatic and steric fields and had a moderate Q (2) = 0.503. CoMSIA analysis surpassed the CoMFA results: the best CoMSIA model included only the hydrophobic field and had a Q (2) = 0.661. In addition, this model predicted adequately the peptides contained in the test set. Our model identified that the potency of delta opioid activity of rubiscolin analogues essentially exhibited a significant relationship with local hydrophobic and hydrophilic characteristics of amino acids at positions 3, 4, 5, and 6. 相似文献
15.
Hou DX Masuzaki S Tanigawa S Hashimoto F Chen J Sogo T Fujii M 《Journal of agricultural and food chemistry》2010,58(24):12735-12743
Oolong tea theasinensins are a group of tea polyphenols different from green tea catechins and black tea theaflavins. The present study reports the inhibitory effects of oolong tea theasinensins on the expression of cyclooxygenase-2 (COX-2) and underlying molecular mechanisms in lipopolysaccharide (LPS)-activated murine macrophage RAW264 cells. The structure-activity data revealed that the galloyl moiety of theasinensins played an important role in the inhibitory actions. Theasinensin A, a more potent inhibitor, caused a dose-dependent inhibition of mRNA, protein, and promoter activity of COX-2. An electrophoretic mobility shift assay (EMSA) revealed that theasinensin A reduced the complex of NF-κB- and AP-1-DNA in the promoter of COX-2. Signaling analysis demonstrated that theasinensin A attenuated IκB-α degradation, nuclear p65 accumulation, and c-Jun phosphorylation. Furthermore, theasinensin A suppressed the phosphorylation of MAPKs, IκB kinase α/β (IKKα/β), and TGF-β activated kinase (TAK1). These data demonstrated that the down-regulation of TAK1-mediated MAPKs and NF-κB signaling pathways might be involved in the inhibition of COX-2 expression by theasinensin A. These findings provide the first molecular basis for the anti-inflammatory properties of oolong tea theasinensins. 相似文献
16.
Breme K Fernandez X Meierhenrich UJ Brevard H Joulain D 《Journal of agricultural and food chemistry》2007,55(5):1932-1938
New, odorant nitrogen- and sulfur-containing compounds are identified in cress extracts. Cress belongs to the botanical order Brassicales and produces glucosinolates, which are important precursors of nitrogen- and sulfur-containing compounds. Those compounds often present low perception thresholds and various olfactive notes and are thus of interest to the flavor and fragrance chemistry. When the study of organonitrogen and organosulfur compounds is undertaken, Brassicale extracts are one of the matrices of choice. Cress extracts were studied by analytical (GC-MS, GC-FPD) and chemical (fractionation) means to identify new interesting odorant compounds. Two compounds that have never been reported in cress extracts, containing both nitrogen and sulfur, were discovered: N-benzyl O-ethyl thiocarbamate and N-phenethyl O-ethyl thiocarbamate. These two molecules being of organoleptic interest, their homologues were synthesized and submitted to organoleptic tests (static and GC-sniffing). Their odors evolve from garlic and onion over green, mushroom- and cress-like to fresh, spearmint-like. This paper presents the origin, chemical synthesis, and organoleptic properties of a series of O-alkyl thiocarbamates. 相似文献
17.
Johanna Bartling Michael Schloter Berndt-Michael Wilke 《Biology and Fertility of Soils》2010,46(3):299-302
Ethyl tert-butyl ether (ETBE) and tert-amyl methyl ether (TAME) are synthetic compounds that are used as gasoline additives in order to reduce emissions from vehicles.
In the present study, effects of these compounds were investigated on the dynamics of inorganic N in soil. Therefore, soil
samples with different water contents were contaminated with ETBE and TAME, respectively. It could be shown that in the presence
of TAME and ETBE, NH4+–N accumulated; moreover, ETBE addition to soil resulted in increased NO2−–N concentrations. These results indicated for the first time that ETBE and TAME can affect nitrification in soil. Thus, their
impact on soil ecology should be investigated more intensively. 相似文献
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Odbayar TO Badamhand D Kimura T Takashi Y Tsushida T Ide T 《Journal of agricultural and food chemistry》2006,54(21):8261-8265
The physiological activities of some phenolic compounds affecting hepatic fatty acid synthesis in mice were compared. Male ICR mice were fed an experimental diet containing 1% quercetin dihydrate, rutin, or ferulic acid or a control diet free of phenolic compounds for 15 days. Quercetin significantly lowered serum cholesterol and phospholipid levels in mice. Also, the serum triacylglycerol level was considerably lower in mice fed the quercetin-containing diet than in those fed a diet free of phenolic compounds, although the difference was not significant. Rutin and ferulic acid did not affect these parameters. Quercetin significantly reduced the activity and mRNA levels of various enzymes involved in hepatic fatty acid synthesis. Rutin reduced a few of the parameters for lipogenesis, but ferulic acid did not affect any of the parameters. It was suggested that a reduction in hepatic lipogenesis is the mechanism underlying the hypolipidemic effect of quercetin. 相似文献