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1.
Nucleophilic substitution of 4-chloro-3-nitro-2-oxo-2H-chromen-2-one 3 by 6-chloro-7H-purin-2-ylamine (a), yielded the corresponding 4-(6-chloro-7H-purin-8-ylamino)-3-nitro-chromen-2-one 4. The chemical structure of synthesized compound was characterized using IR and NMR spectra, and elemental analyses. The purified synthesized compound 4 was tested at concentrations 1, 3, 5 mg/ml for its antibacterial activity against three bacterial cultures: Staphylococcus aureus, Escherichia coli, and Bacillus cereus. The antibacterial activity of synthesized compound was compared to antibacterial activity of standard antibiotics cephalexine and streptomycin. 相似文献
2.
A new series of 5- or 7-substituted 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}-indolin-2-one derivatives were screened for in vitro antioxidant and antimicrobial activities. The results of this study revealed that all synthesized compounds were significantly scavenged DPPH free radicals in a concentration-dependant manner. The IC50 values of all test compounds were found to be between 18.34 and 50.54?µM. All compounds significantly inhibited growth of bacteria and most of the minimum inhibitory concentration values were between 20 and 100?mg?mL?1 indicating potent to moderate antibacterial activity. In conclusion, 3-{4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenylimino)-5 or 7-substituted indolin-2-ones derivatives exhibited moderate antioxidant and antimicrobial activities. 相似文献
3.
A series of sixteen 2-oxo-3-(arylimino) indolin-1-yl)-N-aryl acetamide derivatives were synthesized, characterized by physical and spectral data (IR, 1H nuclear magnetic resonance (NMR), and mass spectrometry), and evaluated for their antibacterial and antifungal activities against various pathogenic microorganisms. Some of the synthesized compounds showed promising antibacterial and antifungal activities, the best being 2-(3-(4-chlorophenylimino)-2-oxoindolin-1-yl)-N-(3-methoxyphenyl) acetamide. 相似文献
4.
Chinnasamy Rajaram Prakash Theivendran Panneerselvam Sundararajan Raja 《毒物与环境化学》2013,95(8):1397-1407
In the present study, a series of novel Schiff bases of isatin were synthesized by condensation of imesatin with different aromatic aldehydes. The imesatins were synthesized by reaction of isatin with p-phenylenediamine. The chemical structures of the synthesized compounds were confirmed by means of IR, 1H-NMR, 13C-NMR, mass spectroscopy, and elemental analysis. These compounds were screened for antioxidant activity by DPPH, nitric oxide and hydrogen peroxide radical scavenging activity. In all the methods, the compound 3-(4-(3,4,5-trimethoxy benzylideneamino)phenylimino) indoline-2-one (5d) showed highest antioxidant activity because of the presence of electron donating groups and the compound 3-(4-(4-nitrobenzylideneamino)phenylimino) indoline-2-one (5f) showed the least activity because of the presence of an electron withdrawing group. 相似文献
5.
3,4-Annelated coumarin-pyrimido-pyrimidine systems (7-imino-8-mercapto-7H-5-oxa-7a,9,12-triaza-benzo[a]anthracen-6-one 2 and 8-hydroxy-7-imino-10-methyl-7H-5-oxa-7a,9,12-triaza-benzo[a]anthracen-6-one 3) were synthesized by the action of 4-amino-2-mercapto-pyrimidine, 2-amino-4-hydroxy-6-methylpyrimidine, respectively, on 4-chlorocoumarin-3-carbonitrile 1. The synthesized compounds were examined for in vitro antibacterial activity against 4 bacterial cultures: Staphylococcus aureus, Streptococcus pneumonia, Escherichia coli, and Aeromonas Salmonicida. The antibacterial activity of synthesized compounds 2 and 3 was compared to antibacterial activity of novobiocin as a standard drug. 相似文献
6.
Design,synthesis, antinociceptive,and anti-inflammatory properties of thiazolopyrimidine derivatives
Ten 2-(substituted benzylidene)-7-(4-chlorophenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one derivatives were synthesized and evaluated. A series of heterocyclic, 2-(substituted benzylidene)-7-(4-chlorophenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one were synthesized by reaction of 7-(4-chloro phenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one with appropriately substituted aldehydes in the presence of anhydrous sodium acetate and glacial acetic acid. The antinociceptive activity was evaluated by tail-flick technique, anti-inflammatory activity was evaluated by carrageenan-induced paw edema test and their ulcerogenicity index was determined. The para-substituted methyl, hydroxy, fluoro, chloro, bromo, and nitro derivatives showed significant antinociceptive and anti-inflammatory activities. The detailed synthesis, spectroscopic data, and pharmacological screening of the synthesized compounds were reported. 相似文献
7.
The curculionid beetle Naupactus
bipes (Germar, 1824) (Coleoptera: Curculionidae: Brachycerinae) has shown feeding preference for leaves of Piper gaudichaudianum, demonstrating an unexpected specificity for an insect considered to be a generalist. The leaves of P. gaudichaudianum contain the prenylated chromenes gaudichaudianic acid (4, major compound) and its methyl ester (5) in addition to a chromene (3) lacking one prenyl residue. In addition to 4, roots contain the chromone methyl ester (1) and methyl taboganate (2, major compound). Feeding on roots, larvae of N. bipes sequester exclusively the root-specific compounds 1 and 2. Adult beetles sequester the leaf-specific chromenes 3 and 4, but were found to also contain compounds 1 and 2 that are absent in leaves. Therefore, it is suggested that 1 and 2 are sequestered by larvae and can be found in the body of adult insects after long-term storage. In addition, 3 and 4, the major compounds in leaves were found to be associated with the eggs. 相似文献
8.
Synthesis of novel benzo[d]imidazolyldihydrospiro[indoline-3,1′-isoindole]-2,4′,7′-triones has been described. The key intermediate 2-[(2-sulfanyl-1H-benzo[d]imidazol-5-yl)amino]acetic acid is obtained by reacting 5-amino-2-mercapto benzimidazole and chloroacetic acid. The three-component reaction of 2-[(2-sulfanyl-1H-benzo[d]imidazol-5-yl)amino]acetic acid with isatin and 1,4-benzoquinone in the presence of 10 mol% of L-proline at ambient temperature afforded 2′-(2-mercapto-1H-benzo [d] imidazol-5-yl)-3′,3a′-dihydrospiro[indoline-3,1′-isoindole]-2,4′,7′(2′H,7a′H)-triones. All the synthesized compounds were evaluated for in vitro anti-inflammatory activity. 相似文献
9.
Gas chromatography with simultaneous flame ionisation and electroantennographic detection (GC–EAD) and gas chromatography
with mass spectrometry analysis (GC–MS) of abdominal extracts of adult male Dermestes haemorrhoidalis Kuster (Coleoptera: Dermestidae) revealed the presence of electrophysiologically and behaviourally active compounds to its
conspecific males and females. Isopropyl dodecanoate (3), isopropyl (Z)-9-tetradecenoate (5), isopropyl tetradecanoate (6), isopropyl (Z)-9-hexadecenoate (7) and isopropyl hexadecanoate (8) were detected in male abdominal extracts only. Analysis of collected
male headspace volatiles revealed the presence of six EAD-active compounds (3), (5), (6) and isopropyl tridecanoate (4) plus
two unidentified compounds (1) and (9). Synthetic compounds (3), (4), (5), (6) and (7) showed EAD activity with antennae of
both sexes in contrast to synthetic (8) which showed EAD activity with female antennae only. Male and female antennae of D.
haemorrhoidalis reacted with high receptor potentials to isopropyl (Z)-9-dodecenoate (2), although this compound itself was detected in neither male nor female abdominal extracts or headspace
volatiles. Petri dish bioassays indicated that male abdominal extracts and compounds (2), (3), (5) and (6) aroused and attracted
conspecific male and female beetles significantly (P < 0.05) compared to female extracts. These results suggested the presence of a male-produced aggregation pheromone in D. haemorrhoidalis. Field assays with any of the described compounds, however, did not result in attraction of this beetle in significant numbers. 相似文献
10.
Nataliya Voloshchuk Mona Knop Thomas Colby Erich Kombrink Lothar Hennig Diana Hofmann Dieter Sicker Andrej Gryganski Margot Schulz 《Chemoecology》2007,17(1):1-12
Summary. Doratomyces stemonitis (Hyphomycetales, Dematiaceae) is a saprotrophic fungus belonging to the mycobiota of the cereal rhizosphere. The fungus is
able to metabolize benzoxazolin-2-(3H)-one and a variety of its derivatives including higher plant detoxification products, microbial degradation products and
the chemically rather stable 2-amino-(3H)-phenoxazin-3-one. D. stemonitis can use all of these compounds as sole C-sources but their utilization, especially that of microbial degradation products
and 2-amino-(3H)-phenoxazin-3-one, seems to be highly energy consuming, resulting in slow mycelium growth and a change of colony morphology.
Benzoxazolin-2-(3H)-one derived compounds induce the synthesis of different isoforms of a glycosylated protein with sequence homologies to the
endo-1,3-β-glucanase Asp f2, an allergen from Aspergillus fumigatus and other Asp f2-like proteins e.g., from Verticillium dahliae or PRA1 antigen from Candida albicans. The induction of the protein is regarded as a stress response. 相似文献
11.
Ahmed O. Maslat Raad Al-Hamdany Zacharia Fataftah Alaa. J. Mahrath Mahmoud J. Abussaud 《毒物与环境化学》2013,95(4-6):149-157
A number of newly synthesized phthalidylamines and o-benzoylbenzamide derivatives were evaluated for some biological activities. Synthesis was established by condensation of 3-acetoxyphthalide 1 with morpholine, piperidine, N,N-diisobutyl-N,N-dibenzylamines and piperazine, which afforded N-(3-phthalidyl)amines 3a–d, and 4 respectively, while with N,N-diisopropylamine, o-formyl-N,N-diisopropyl benzamide 5a is formed exclusively. On the other hand, the reaction of 3-acetoxy-3-phenylphthalide 2 with secondary amines afforded o-benzoylbenzamide derivatives 5b–c, 6 in a high yield. The structure of the reaction products was established from their spectral data. These products were screened for antifungal, antibacterial and genotoxic effect. It was found that all tested compounds have antifungal activity. Compounds 1, 2, 3d and 5b were found to be active against Escherichia coli, Bacillus subtilis and Staphylococcus aureus. Genotoxic effects using Ames test showed that Compounds 1 and 2 have a weak base-pair substitution mutagenicity while a clear base-pair substitution mutagenic activity was shown by 3a using TA100-strain of Salmonella typhimurium. Compound 4 showed a frameshift mutgenicity while a weak oxidative mutagenic action was revealed by 6. No change on the mutagenicity of the tested chemicals was observed after using the S9 metabolic activation system. 相似文献
12.
Yorianta?Sasaerila Regine?Gries Gerhard?Gries Grigori?Khaskin Skip?King Stephen?Takács Hardi?) 《Chemoecology》2003,13(2):89-93
Summary. During peak calling activity by male oil palm bunch
moths, Tirathaba mundella Walker (Lepidoptera: Pyralidae), their
hairpencils, wings or entire body were extracted in hexane. Gas
chromatographic-electroantennographic detection (GC-EAD) analyses of
hair pencil extracts revealed four compounds that consistently elicited
responses from female antennae. The NMR spectrum of isolated compound 1,
and mass spectra and retention indices of compounds 1–4 suggested that
they were (3S,6S)-2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-ol (1),
4-hydroxy-3-methoxy-benzaldehyde (2, vanillin),
6,10,14-trimethyl-2-pentadecanone (3), and
6,10,14-trimethyl-2-pentadecanol (4). Comparative GC and GC-MS analyses
of hair pencils extract and synthetic standards confirmed these
structural assignments. Moreover, comparative chromatography of
synthetic and hairpencil-isolated 1 on a Cyclodex-B column (which
separated the four stereoisomers with baseline resolution) revealed that
male T. mundella produce the SS-stereoisomer (SS-1). In field cage
bioassay experiments in Palembang, Indonesia, synthetic SS-1 and
vanillin in combination, but not singly, attracted female T. mundella.
SS-1 plus vanillin were as effective as male T. mundella in attracting
females. Compounds 3 and 4 did not enhance the blend's attractiveness.
Received October 11 2002; accepted March 14, 2003.
R1D="
Correspondence to: Gerhard Gries, email: gries@sfu.ca 相似文献
13.
A new series of 3-phenoxyazetidin-2-ones (β-lactams) were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. In this study, the effects of a synthetic of β-lactam-structured COX-2 inhibitor with 4-(4-(methylsulfonyl)phenyl)-3-phenoxy-1-phenylazetidin-2-one on cell viability of cancerous lymphoblast isolated from patients diagnosed with acute lymphocytic leukemia (ALL) and normal lymphocytes collected from healthy donors were investigated. The viability % of cancer lymphoblast and normal lymphocyte treated 4-(4-(methylsulfonyl)phenyl)-3-phenoxy-1-phenylazetidin-2-one were tested with MTT assay. Apoptosis and necrosis were measured by double stains of annexin V and propidium iodide, and caspase-3 as a final mediator in apoptotic death measured by colorimetric assay. Mitochondria were isolated from both cancerous lymphoblast and normal lymphocytes to measure parameters of mitochondrial damage such as reactive oxygen species (ROS) formation, mitochondrial membrane potential decrease, swelling, and cytochrome c release following the administration of azithidine-2-one derivative, 4-(4-(methylsulfonyl)phenyl)-3-phenoxy-1-phenylazetidin-2-one. Our results showed that 4-(4-(methylsulfonyl)phenyl)-3-phenoxy-1-phenylazetidin-2-one inhibited proliferation of cancerous lymphoblast in a concentration-dependent manner by inducing apoptosis but not in normal lymphocytes. Treatment with azithidine-2-one derivative produced a rapid loss of mitochondrial transmembrane potential, stimulation of release of ROS and mitochondrial cytochrome c into cytosol, and subsequent induction of procaspase-9 processing. Data suggest that 4-(4-(methylsulfonyl)phenyl)-3-phenoxy-1-phenylazetidin-2-one-induced ROS production led to mitochondria-mediated death signaling that resulted in apoptosis in cancerous lymphoblast cells. The induction of apoptosis by azithidine-2-one compounds, such as 4-(4-(methylsulfonyl)phenyl)-3-phenoxy-1-phenylazetidin-2-one, may provide a mechanism for its cancer chemopreventive action in acute lymphocytic leukemia cells. 相似文献
14.
Kristin von Hirsch Svendsen Sindre Rabben Svedahl Christian H. Lindh Karin Broberg Palmgren 《毒物与环境化学》2017,99(3):525-534
Cooking fumes contain compounds that may give rise to oxidative stress and mutations when inhaled. The aim of this study was to evaluate if cooking fumes from frying of bacon induce oxidative stress by measurement of urinary 8-oxo-7,8-dihydro-2 deoxyguanosine, a marker of oxidatively damaged DNA. Three non-smoking women fried bacon for 3 h. Urine samples were taken as early morning void at the same time on four days; the morning before frying, the morning after first frying, the morning after three days of frying and one week after first urine sample. 8-Oxo-7,8-dihydro-2 deoxyguanosine, 1-hydroxypyrene and 2-hydroxyphenanthrene, metabolites of polycyclic aromatic hydrocarbons, were measured by liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS). 8-Oxo-7,8-dihydro-2 deoxyguanosine correlated weakly with concentrations of 1-hydroxypyrene (r = 0.31, p = 0.042), but it did not correlate with 2-hydroxyphenanthrene (r = ?0.074; p = 0.64). Average urinary 8-oxo-7,8-dihydro-2 deoxyguanosine concentrations increased from the day before frying (16.3 ± 4.2 nmol/L) to the third day of frying (26.2 ± 10.2 nmol/L), although not statistically significantly. Our pilot study shows that frying of bacon may result in increased oxidative stress which further emphasises the possible carcinogenic potential of cooking fumes. 相似文献
15.
Summary Males ofCarpophilus freemani Dobson (Coleoptera: Nitidulidae) produce an aggregation pheromone to which both sexes fly in a wind-tunnel bioassay. The major pheromone component (ca. 30 ng per male per day in volatile collections) was identified as (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene. A minor component, (2E,4E,6E,8E)-7-ethyl-3,5-dimethyl-2,4,6,8-undecatetraene, was 3–10% as abundant as the major triene and was 5–20% as active when compared at relative doses ranging from natural proportions to 1:1. These compounds act synergistically: a mixture of major and minor components in natural proportions attracted more than twice as many beetles as the major component alone, and the mixture fully accounted for the activity of male-derived volatile collections. Six other male-derived conjugated hydrocarbons, ranging from 2% down to 0.04% as abundant as the major component, were also identified. These are (in order of decreasing bioassay activity when compared on an equal-weight basis): (3E,5E,7E)-6-ethyl-4-methyl-3,5,7-decatriene, (2E,4E,6E)-5-ethyl-3-me-thyl-2,4,6-octatriene, (3E,5E,7E,9E)-8-ethyl-4,6-dimethyl-3, 5,7,9-dodecatetraene, (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6, 8-undecatetraene, (3E,5E,7E)-5-ethyl-7-methyl-3,5,7-undecatriene, and (2E,4E,6E)-3,5-dimethyl-2,4,6-nonatriene. All structure identifications were confirmed by synthesis. In the wind tunnel, the pheromone acted synergistically with host-type volatiles such as propyl acetate, valeric acid, and ethanol. This concept was verified by fields tests in California, in which there was dramatic synergism between the pheromone and fermenting host materials. Pheromone biosynthesis is discussed. 相似文献
16.
Summary. The basic chemical structure of the sex
pheromone of the pine sawfly Microdiprion pallipes
(Fallén) has earlier been identified as the propionate
ester of (2S,3S,7R/S,11R/S)/(2R,3R,7R/S,11R/S)-3,7,11-
trimethyl-2-tridecanol. We now report the results from
further investigations on the male response to individual
stereoisomers and to blends of stereoisomers, both in electroantennographic
(EAG) recordings and in field trapping
experiments. We also present our attempts to determine the
stereochemistry of the compounds present in females of
M. pallipes. By comparing gas chromatograms and mass
spectra obtained from natural extracts with those from synthetic
compounds it was found that the females contain one
or more of the four (2S,3S,7R/S,11R/S)-3,7,11-trimethyl-2-
tridecanol isomers (SS++-1). The active pheromone component
is the corresponding propionate ester 2. In EAG
experiments, males responded most strongly to five propionate
ester samples, namely two four-isomer blends: SS++-2
and SR++-2, and three individual stereoisomers: SSSR-,
SRRR- and SRSR-2. In a series of field trapping experiments
it was found that males were attracted to the SR++-2
four-isomer blend and to the individual isomer SSSR-2.
Based on the EAG-recordings and field responses of males
and the stereoisomers found in the females, we suggest that
the propionate ester of (2S,3S,7S,11R)-3,7,11-trimethyl-2-
tridecanol (SSSR-2) is used as a main component of the sex
pheromone in M. pallipes. Apparently the males react to
other stereoisomers in addition to that or those produced by
the females. 相似文献
17.
曲霉sp.136的化学成分研究 总被引:2,自引:0,他引:2
从曲霉sp.136的固体发酵物中分离得到6个化合物.应用波谱分析及与已知品对照的手段将它们鉴定为烟曲霉酸(1)、(20S,22E,24R)-5α,8α-表二氧-麦角甾-6,22-二烯-3β-醇(2)、β-谷甾醇(3)、(2S,3S,4R)-2-[(2′R)-2′-羟基二十四烷酰氨基]-1,3,4-三羟基十八烷(4)、4-羟基苯乙酸(5)和烟碱酸(6).图1参5 相似文献
18.
Cesar Rodriguez-Saona Therese M. Poland James R. Miller Lukasz L. Stelinski Gary G. Grant Peter de Groot Linda Buchan Linda MacDonald 《Chemoecology》2006,16(2):75-86
Summary. We investigated the volatile emissions of Manchurian ash seedlings, Fraxinus mandshurica, in response to feeding by the emerald ash borer, Agrilus planipennis, and to exogenous application of methyl jasmonate (MeJA). Feeding damage by adult A. planipennis and MeJA treatment increased volatile emissions compared to unexposed controls. Although the same compounds were emitted
from plants damaged by beetles and treated with MeJA, quantitative differences were found in the amounts of emissions for
individual compounds. Adult virgin female A. planipennis were similarly attracted to volatiles from plants damaged by beetles and those treated with MeJA in olfactometer bioassays;
males did not respond significantly to the same volatiles. Coupled gas chromatographic-electroantennogram detection (GC-EAD)
revealed at least 16 antennally-active compounds from F. mandshurica, including: hexanal, (E)-2-hexenal, (Z)-3-hexen-1-ol, 3-methyl-butylaldoxime, 2-methyl-butylaldoxime, (Z)-3-hexen-1-yl acetate, hexyl acetate, (E)-β-ocimene, linalool, 4,8-dimethyl-1,3,7-nonatriene, and E,E-α-farnesene. Electroantennogram (EAG) dose–response curves using synthetic compounds revealed that females had a stronger
EAG response to linalool than males; and male responses were greater to: hexanal, (E)-2-hexenal, (Z)-3-hexen-1-ol, 3-methyl-butylaldoxime, 2-methyl-butylaldoxime, and hexyl acetate. These results suggest that females may
use induced volatiles in long-range host finding, while their role for males is unclear. If attraction of females to these
volatiles in an olfactometer is upheld by field experiments, host plant volatiles may find practical application in detection
and monitoring of A. planipennis populations. 相似文献
19.
Teodora B. Toshova Dimitar I. Velchev Mitko A. Subchev Miklós Tóth József Vuts John A. Pickett Sarah Y. Dewhirst 《Chemoecology》2010,20(3):199-206
The grey corn weevil, Tanymecus (Episomecus) dilaticollis, is an economically important polyphagous pest in Eastern and Central Europe. The present research is the first published
electrophysiological study of olfactory sensitivity of adult T. dilaticollis to plant volatiles. The electrophysiological responses of male and female antennae were recorded to 20 synthetic volatile
organic compounds (VOCs), previously identified to be released from the preferred host plants, maize and sunflower. Antennae
of both sexes responded to a wide range of volatiles from different chemical classes: fatty acid derivatives, aromatic compounds
and terpenoids. Two green leaf volatiles, (E)-2-hexen-1-ol and (Z)-3-hexen-1-ol, and one terpenoid, (±)-linalool, elicited the strongest electrophysiological responses by male and female
antennae. Relatively high electrophysiological activity by T. dilaticollis antennae was also recorded to benzaldehyde, eugenol and caryophyllene. In the field, (E)-2-hexen-1-ol and (Z)-3-hexen-1-ol, when presented individually, caught significantly more male and female T. dilaticollis than unbaited controls. These compounds could be developed into an attractive trap for the detection and monitoring of T. dilaticollis. 相似文献
20.
Andrés González Frank C. Schroeder Athula B. Attygalle Aleš Svatoš Jerrold Meinwald Thomas Eisner 《Chemoecology》1999,9(3):105-112
Summary. Female Photuris fireflies sequester defensive steroidal pyrones (lucibufagins) from male fireflies of the genus Photinus. Lucibufagin analyses of Photuris females and Photinus ignitus males show that the lucibufagin mixtures of predator and prey differ in their composition. Analyses of whole body extracts
showed that P. ignitus males contain a mixture of eight non-glycosylated lucibufagins, composed mostly of compounds with two oxygenated positions
in the steroidal A-ring (C-3, C-5). After feeding on P. ignitus males, Photuris females contain six major lucibufagins. Three of these compounds are not present in the prey, including the novel lucibufagin
glycoside 5β,11α-dihydroxy-12-oxo-3β-O-β-D-xylopyranosylbufalin, and two other lucibufagins with a trioxygenated A-ring (C-2,
C-3, C-5). These results indicate that Photuris females transform the sequestered lucibufagins both by glycosylation and oxidation, which could affect the systemic transportability
of these compounds due to an increase in their polarity.
Received 18 February 1999; accepted 19 April 1999. 相似文献