新型杀虫剂丁香酚酯的设计合成和活性初测

拟除虫菊酯具有高效、对哺乳类动物低毒、无环境残留的优点,是新一代绿色仿生农药.由于近二十年大量使用,其抗药性已渐明显.因此大力发展和自主研制新品种是一项迫切关系国计民生的重要课题[1,2].     

两种卤代菊酸含氟对甲氧甲基苄酯的合成及其杀虫活性

报道了两种含氟对甲氧甲基苄酸类拟除虫菊酯新化合物，即三氟甲基氯菊酸含 氟对甲氧甲基苄酯和二溴菊酸含氟对甲氧甲基苄酯的合成。生物活性测试的结果表 明该化合物对家蝇显示出较高的杀虫活性和较低的抗性。     

一些新拟除虫菊酯化合物的合成

本文采用几种不同于速灭菊酯的醇组份合成了十七个新拟除虫菊酯化合物。分别用红外光谱、核磁共振谱、质谱及元素分析等方法确定了它们的结构,并选择了家蝇、蚜虫、粘虫、拟谷(虫甲)、红蛛蜘等昆虫作了生物活性的测定。其中,醇组份为和的新拟除虫菊酯化合物具有较好的杀虫、杀螨活性。     

新型含异噁唑环拟除虫菊酯的合成及生物活性(Ⅱ)

前文［１］我们报道了含异唑环的醚菊酯类化合物的合成。本文报道四种菊酸（１）与五种３－取代苯基－５－溴甲基异唑（２）在ＫＦ·２Ｈ２Ｏ的催化下，合成１５个新的拟除虫菊酯类化合物（３）。所有新化合物均通过了红外光谱、核磁共振及元素分析的结构鉴定。１实验...     

新型非酯型拟除虫菊酯的合成

传统拟除虫菊酯类杀虫剂均含有一个酯基^[1,2],近年来,在保持分子整体空间结构不变的情况下,用其它功能基替换酯基,合成了非酯型的拟除虫菊酯^[3],式1所示结构的化合物具有良好的生物活性^[4],其中碳碳键或碳氧键 取代了传统拟除虫菊酯中的酯基,在主链结构上含有偕二甲基和3－苯氧基苯基,二是该结构中决定生物活性的主要基因^[5,6],在此结构的基础上已醚菊酯^[6],烃菊酯^[4]和酮菊酯^[7]等高效低毒,结构简化的除除虫菊酯类杀虫剂,而醚菊酯MTI－800已商品化,作为式1所示结构 新尝试,我们在保留2在性部分外,用环戊烯基取代直链烯烃,合成了一种非酯型的拟除虫菊酯（即1－甲基－1－苯基－1－[3-（3－苯氧基）苯基]环戊烯基－乙烷）（9）,其合成路线如式2。     

拟除虫菊酯筛选及分子设计

综述了拟除虫菊酯的进展及新拟除虫菊酯的筛选和分子设计的方法等。参考文献５８篇。     

蔬菜中拟除虫菊酯类杀虫剂多残留气相色谱检测方法

本文介绍了6种拟除虫菊酯杀虫剂在蔬菜中的双柱单检测器多残留分析方法。样品用丙酮提取,弗罗里硅土净化,气相色谱电子捕获检测器定量测定。经对黄瓜、番茄、大白菜、青椒进行添加回收率试验,其回收率在87.6%～105.1％之间,变异系数1.2～7.2%。最低检出浓度0.001～0.10mg/kg。     

Synthesis and bioactivity evaluation of eugenol hybrids obtained by Mannich and 1,3 dipolar cycloaddition reactions

Design, synthesis, and bioactivity evaluation of novel mannich bases ( 2a-2j ) and triazole-chalcone derivatives ( 7a-7k ) of Eugenol 1 were reported. Among all the derivatives tested for antiproliferative activity, di-amine manich derivative 2b (32.92 μM), and 4-methoxy chalcone triazole derivative 7d (33.05 μM) significantly inhibited HepG2 cell lines when compared to the standard doxorubicin (37.29 μM). Whereas most of the compounds such as diethylamine 2a (17.75 μM), (aminomethyl) methane diamine 2b (17.02 μM), and bis (chloromethyl) amine 2c (20.12 μM) showed moderate to better inhibition towards MCF-7 cell lines. The synthesized analogues were also tested for antidiabetic and antiobesity potentials. Compounds 2f (55.50%), 2c (54.34%), 7g (55.5%), and 2a (55.5%) have shown moderate inhibitory potentials toward intestinal α-glucosidase enzyme when compared to the standard Acarbose (72.86%). Likewise, compounds 7d (82.95%), 7f (76.19%), 7g (74.81%), 7e (74.81%), and 2g (72.50%) have shown significant to moderate inhibitory potentials toward Pancreatic lipase enzyme when compared to the standard orlistat (91.10%). ROS induces life-threatening diseases like diabetes, cancer, etc., and antioxidants play a major role in controlling their production. Compounds 2c (99.81%), 2i (99.80%), 2d (99.26%), 2g (98.79%), and 2f (98.42%) have shown significant antioxidant profiles in ABTS assay when compared to the standard Trolox (99.07%). Further, In silico Molecular docking and pharmacokinetic screening of the eugenol derivatives complemented the in vitro results indicating the drug likeness of the obtained active compounds.     

N-酰基吡唑衍生物的合成与生物活性

N-酰基吡唑衍生物的合成与生物活性;拟除虫菊酯;1H吡唑衍生物;合成;生物活性     

Synthesis,characterization, and biological evaluation of new heterocyclic systems 1, 2, 3-triazole-isoxazoline from eugenol by the mixed condensation reactions

Abstract

We report the synthesis of new series of heterocyclic systems eugenol 1 derivatives by the mixed condensation reaction of 1,3-dipolar azide and the oxide of p-chlorophenylnitrile on the 4-allyl-2-methoxy-1-(prop-2-yn-1-yloxy)benzene 2. The mono and bicycloadducts, whose structure is homologous to compounds having a broad spectrum of activity, were obtained in good yields. The monocondensation reaction of azides on 4-allyl-2-methoxy-1-(prop-2-yn-1-yloxy)benzene 2 is completely chemoselective, regioselective and stereospecific. The condensation of nitrile oxide on 1,2,3-triazole monocycloadducts prepared was chemoselective and regioselective. The structure of all cycloadducts were characterized and confirmed by the ¹H, ¹³C, 2D nuclear magnetic resonance and mass spectrometry analysis. All the newly synthesized mono and bis-heterocyclic compounds have been selected for their antiproliferative activity against HT-1080 fibrosarcoma, A549 lung carcinoma, and MCF-7 and MDA-MB-231 breast carcinoma cell lines. Among the derivatives, only the compounds 4a, 4b, 5a, 5b, 5d, 5e and 5g showed significant cytotoxicity with IC₅₀ values ranging from 15.31 to 18.81?µM against HT-1080 cells, and 17.32 to 25.94?µM against the other cell lines.     

Synthesis and properties of optically active amino acid based polyacetylenes bearing eugenol and fluorene moieties

Novel optically active amino acid based polyacetylenes bearing eugenol and fluorene moieties were synthesized, and their properties, including chiroptical ones, were analyzed. N‐[1‐(3,4‐Dimethoxyphenyl)‐2‐propyloxycarbonyl]‐L ‐alanine N′‐propargylamide ( 1 ), N‐[1‐(3,4‐dimethoxyphenyl)‐2‐propyloxycarbonyl]‐L ‐alanine propargyl ester ( 2 ), N‐(9‐fluorenylmethoxycarbonyl)‐L ‐alanine N′‐propargylamide ( 3 ), and N‐(9‐fluorenylmethoxycarbonyl)‐L ‐alanine propargyl ester ( 4 ) were polymerized with a rhodium‐zwitterion catalyst in tetrahydrofuran to afford the corresponding polymers with moderate molecular weights ranging from 10,800 to 17,300 in good yields. Because of the large specific rotation and circular dichroism (CD) signal, it was concluded that the poly(N‐propargylamide)s [poly( 1 ) and poly( 3 )] took a helical structure with a predominantly one‐handed screw sense. The solvent and temperature could tune the helical structure of poly( 1 ). On the other hand, the poly(propargyl ester)s [poly( 2 ) and poly( 4 )] exhibited only small specific rotations and CD signals. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 810–819, 2006     

Synthesis and spectral characterization of platinum(II) complexes containing eugenol,a natural allylphenol

For the first time, eugenol, a natural bioactive allylphenol, was introduced into coordination with platinum(II) by replacement of ethylene from Zeise’s salt with eugenol (Eug). The obtained complex, K[PtCl₃(Eug)] (1), was used as the key compound for preparation of the series of trans-[PtCl₂(Eug)(Amine)] (2–11), [PtCl(Eug)(8-O-quinoline)] (12) and [PtCl(Eug)(2-O₂C-quinoline)] (13). The synthesized complexes were characterized by elemental analyses, IR, ¹H NMR, ¹³C NMR, HSQS, HMBC, NOESY, and MS spectra. In 1–13 eugenol coordinates with Pt(II) at ethylenic double bond of the allyl group, the donor N of the amines is in trans-position in comparison with the double bond. A display of the trans-effect on the chemical shift of ¹H and ¹³C was remarked. Seven complexes were tested for cell in vitro cytotoxicity on human cancer cells. Complexes 3 and 12 exhibit high activities on Hep-G2 with IC₅₀ = 3.12 and 5.29 μM; 12 gives high activity against KB, Lu and MCF-7 with IC₅₀ = 0.43, 2.95 and 1.84 μM, respectively. Most of these IC₅₀ are lower than those of cisplatin.     

Antioxidant activity and kinetics studies of eugenol and 6-bromoeugenol

In this work, we report the antioxidant and free radical scavenging activity of 6-bromoeugenol and eugenol. EC₅₀, the concentration providing 50% inhibition, is calculated and the antioxidant activity index (AAI) is evaluated. The antioxidant activity was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging method. EC₅₀ values of 6-bromoeugenol, ascorbic acid and eugenol were 34.270 μg/mL, 54.888 μg/mL and 130.485 μg/mL, respectively. 6-Bromoeugenol showed higher AAI value (1.122) followed by ascorbic acid (0.700), then by eugenol (0.295). We also investigate the kinetics of DPPH radical scavenging activity of our products to determine the useful parameter TEC₅₀ to evaluate their antiradical efficiency (ARE). Our results have shown high ARE. This study has provided the following ARE ( × 10^? 3) order for the tested antioxidants: ascorbic acid (70.119)>6-bromoeugenol (34.842) > eugenol (21.313). Finally, we classify ascorbic acid and eugenol as fast kinetics reaction (TEC₅₀ 8.82 and 11.38 min, respectively) and 6-bromoeugenol as medium kinetics reaction (TEC₅₀ 39.24 min).     

Synthesis of isoquinoline alkaloid derivatives from eugenol

Alkylation under phase-transfer catalysis conditions (18-crown-6/KOH) of eugenol was used for cyclocondensation with nitriles (Ritter reaction), the products of which were isoquinoline derivatives.     

Green synthesis of silver nanoparticles by using eugenol and evaluation of antimicrobial potential

The importance of green synthesis was revealed with advantages such as: eliminating the use of expensive chemicals; consume less energy; and generate environmentally benign products. With this aim, silver nanoparticles (AgNPs) were synthesized by using isolated eugenol from clove extract. Its antimicrobial potential was determined on three different microorganisms. Clove was extracted and eugenol was isolated from this extract. Green synthesis was performed and an anti‐microbial study was performed. All extraction and isolation analyses were performed by high‐performance liquid chromatography (HPLC); identification and confirmation were achieved using liquid chromatography–mass spectrometry (LC–MS); and scanning electron microscopy was used for characterization. Both HPLC and LC–MS analyses showed that eugenol obtained purely synthesized AgNPs and 20‐25‐nm‐sized and homogeneous shaped particles seen in images. The antimicrobial effects of AgNPs at eight concentrations were determinated against Staphylococcus aureus, Escherichia coli and Candida albicans, and maximum inhibition zone diameters were found as 2.6 cm, 2.4 cm and 1.5 cm, respectively. The results of the antimicrobial study showed that eugenol as a biological material brought higher antimicrobial effect to AgNPs in comparison to the other materials found in the literature.     

5－依维菌素B_(1a)酯的合成和生物活性

依维菌素B_(1a)与羧酸在DMAP/DCC体系中直接酯化，得到10个5-IV B_(1a)酯 衍生物，产率66%～82%；它们的化学结构得到IR，~1H NMR, ~(13)c nmr和MS谱的 确证。它们具有良好的杀虫、杀螨活性。