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1.
Osamu Kirino Shigeo Yamamoto Toshiro Kato 《Bioscience, biotechnology, and biochemistry》2013,77(9):2149-2153
The antifungal activity of 37 N-(methoxy-substituted benzoyl)anthranilic esters was tested on the powdery mildew of barley caused by Erysiphe graminis by the pot test. Among the methyl N-(methoxy-substituted benzoyl)anthranilates tested, 3,4-dimethoxybenzoyl derivative exhibited the highest activity. The variation in fungicidal activity of N-(3,4-dimethoxybenzoyl)anthranilic esters was shown to be related with variation in hydrophobicity and the electronic property of the alcohol moiety of the ester. The branching at the α-position of the alcohol moiety of the ester was detrimental to the activity. 相似文献
2.
《Bioscience, biotechnology, and biochemistry》2013,77(12):2677-2682
A set of N-arylbenzenesulfonamides with various substituents at the arylamine and benzenesulfonyl positions were prepared, and their antifungal properties were measured in vitro against such plant pathogenic fungi as Pythium ultimum, Phytophthora capsici, Rhizoctonia solani, and Botrytis cinerea. Compounds 3, 4, 8, 9, 10, 14, 16, 18, 20, 21, 24 and 27 had antifungal activity over a broad spectrum of the phytopathogenic fungi tested, where 50% of inhibition (ED50) was in the range of 3-15 μg/ml. Based on the in vitro activity, six derivatives (3, 4, 10, 18, 21 and 27) were selected and tested further for their fungicidal efficacy in vivo. The fungicidal efficacy of 10, 21 and 27 had a disease control value of over 85% at 50 μg/ml against wheat leaf rust, while that of 4 was selective against cabbage club root disease. 相似文献
3.
G. Ceulemans K. Khan A. Van Schepdael P. Herdewijn 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):813-816
Abstract Reaction of N-Boc-L-homoserine benzylester with N3 -benzoylthymine under Mitsunobu conditions afforded N-Boc-L-α-amino-γ-N3 -benzoylthymine butyric acid benzylester. After removal of the N-benzoyl and O-benzyl protecting group, this compound was used in solution phase peptide synthesis. 相似文献
4.
Richard J. Kulmacz Alemka Kisic George J. Schroepfer 《Chemistry and physics of lipids》1979,23(4):291-319
The following compounds were prepared by chemical synthesis from tribenzoylsphingosine: (2S,3S,4S)-2-acetamido-1,3,4-trihydroxyoctadecane, (2S,3S,4R)-2-acetamido-1,3,4-triydroxyoctadecane, (2S,3S,5S)-2-acetamido-1,3,5-trihydroxyoctadecane, and (2S,3S,5R)-2-acetamido-1,3,5-trihydroxyoctadecane. These compounds were characterized by melting point determination, low and high resolution mass spectra, infrared, optical rotation, chromatographic, and chemical degradation studies. In addition, each of the compounds was converted to the corresponding free base and N-benzoyl derivative. (2S,3S,4R)-2-Benzylamino-1,3,4-trihydroxyoctadecane was prepared from the N-benzoyl derivative of authentic phytosphingosine. 相似文献
5.
The cytokinin activities of various 6-acylaminopurines, 6-alkylaminopurines, 6-acylamino-9-benzyl-purines as well as a series of isosteric-nitrogen derivatives of N6-(γ, γ-dimethylallyl)adenine (I6Ade) have been tested using the tobacco pith and the pea bud bioassays. The interactions between active, slightly active and inactive compounds have been studied with the last assay. Acylation decreases the biological activity; e.g., N6-benzoyl and N6-furoyladenines are less active than Na6-benzyladenine and kinetin. Substitution at the 9-position reduces (tobacco-pith assay) or suppresses (pea-bud assay) the phytohormonal activity of otherwise active 6-acylaminopurines. In isosteric derivatives, maximum activity occurs when the side chain has the same length as in 16Ade. After the analysis of interactions between more or less active compounds, it is suggested that the differences in cytokinin activity could be related to unequal affinities for a hypothetical receptor site. 相似文献
6.
In our previous work, two dopamine derivatives with benzothiazole fragment were isolated and identified from Polyrhachis dives (P. dives). Based on their characteristic structure, we used them as lead compound to carry out structural optimization and subsequent fungicidal evaluation. Here 20 dopamine derivatives with benzothiazole fragment were designed and synthesized by a facile method, and their structures were characterized by 1H-NMR, 13CNMR and HMRS. In bioassays, most of the title compounds possess potential fungicidal activities against Altenaia alternala (A. alternala) and Botrytis cinerea (B. cinerea). Especially, (E)-N-(2-(benzo[d]thiazol-6-yl)ethyl)-3-(p-tolyl)acrylamide and (E)-N-(2-(benzo[d]thiazol-6-yl)ethyl)-3-(4-(trifluoromethyl)phenyl)acrylamide displayed 29.3 mg/L and 10.7 mg/L EC50 value against A. alternala, respectively, which possessed equivalent fungicidal activities level to hymexazol. 相似文献
7.
Chondroitinase ABC is a lyase that degrades chondroitin sulfate, dermatan sulfate and hyaluronic acid into disaccharides.
The purpose of this study was to determine the ability of chondroitinase ABC to degrade chondroitin sulfate in which the N-acetyl groups are substituted with different acyl groups. The bovine tracheal chondroitin sulfate A (bCSA) was N-deacetylated by hydrazinolysis, and the free amino groups derivatized into N-formyl, N-propionyl, N-butyryl, N-hexanoyl or N-benzoyl amides. Treatment of the N-acyl or N-benzoyl derivatives of bCSA with chondroitinase ABC and analysis of the products showed that the N-formyl, N-hexanoyl and N-benzoyl derivatives are completely resistant to the enzyme. In contrast, the N-propionyl or N-butyryl derivatives were degraded into disaccharides with slower kinetics compared to that of unmodified bCSA. The rate of
degradation of bCSA derivatives by the enzyme was found to be in the order of N-acetyl>N-propionyl>>N-butyryl bCSA. These results have important implications for understanding the interaction of N-acetyl groups of glycosaminoglycans with chondroitinase ABC. 相似文献
8.
Suzuki Yoshihito; Yamaguchi Isomaro; Murofushi Noboru; Takahashi Nobutaka 《Plant & cell physiology》1988,29(3):445-448
The flower-inducing activities in Lemna paucicostata 151 offour major metabolites of benzoic acid (N-benzoyl aspartate,benzyl 6-O-ß-D-apiofuranosyl-O-ß-D-glucopyranoside,O-benzoyl isocitrate and O-benzoyl malate) were measured, andthe effects on the uptake and metabolism of benzoic acid dueto change in the level of the benzoic acid concentration orto the addition of plant hormones were investigated. N-Benzoylaspartate had weak activity, and O-benzoyl isocitrate and malatehad fairly strong activities, while benzyl 6-O-ß-D-apiofuranosyl-ß-D-glucopyranosideshowed no activity. As the concentration of benzoic acid rose,the ratio of N-benzoyl aspartate increased and that of benzyl6-O-ß-D-apiofuranosyl-O-ß-D-glucopyranosidedecreased. GA3 and IAA, inhibitors of flower induction by benzoicacid, seemed to promote conversion to N-benzoyl aspartate insteadof to benzyl 6-O-ß-D-apiofuranosyl-ß-D-glucopyranoside.The conversion to N-benzoyl aspartate was considered to be adetoxification process and that to benzyl 6-O-ß-D-apiofuranosyl-ß-D-glucopyranosidemay be directly related to flower induction in Lemna. (Received November 2, 1987; Accepted January 23, 1988) 相似文献
9.
Nilantha Sirisoma Azra Pervin Hong Zhang Songchun Jiang J. Adam Willardsen Mark B. Anderson Gary Mather Christopher M. Pleiman Shailaja Kasibhatla Ben Tseng John Drewe Sui Xiong Cai 《Bioorganic & medicinal chemistry letters》2010,20(7):2330-2334
As a continuation of our efforts to discover and develop apoptosis inducing N-methyl-4-(4-methoxyanilino)quinazolines as novel anticancer agents, we explored substitution at the 5-, 6-, 7-positions of the quinazoline and replacement of the quinazoline by other nitrogen-containing heterocycles. A small group at the 5-position was found to be well tolerated. At the 6-position a small group like an amino was preferred. Substitution at the 7-position was tolerated much less than at the 6-position. Replacing the carbon at the 8-position or both the 5- and 8-positions with nitrogen led to about 10-fold reductions in potency. Replacement of the quinazoline ring with a quinoline, a benzo[d][1,2,3]triazine, or an isoquinoline ring showed that the nitrogen at the 1-position is important for activity, while the carbon at the 2-position can be replaced by a nitrogen and the nitrogen at the 3-position can be replaced by a carbon. Through the SAR study, several 5- or 6-substituted analogs, such as 2a and 2c, were found to have potencies approaching that of lead compound N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine (1g, EP128495, MPC-6827, Azixa®). 相似文献
10.
Katsumi Shibata 《Bioscience, biotechnology, and biochemistry》2013,77(7):1739-1744
This experiment was performed to investigate the possibility that N′ -methylnicotinamide (N′-methyl-3-pyridinecarboxamide) and nicotinamide N-oxide have niacin activity or not in animals. When 20 mg N′-methylnicotinamide per mouse was administered, urinary excretion of nicotinamide, N1-methylnicotinamide (MNA), N1-methyl-2-pyridone-5-carboxamide (2-Py), and N1-methyl-4-pyridone-3-carboxamide (4-Py) increased 24-, 3-, 3-, and 3-fold, respectively, compared with the control values. The increased ratios of MNA, 2-Py, and 4-Py were almost the same as those when 20 mg nicotinamide was administered. Therefore, the relative activity of N′-methylnicotinamide to nicotinamide as niacin was considered to be about 1. When 20 mg nicotinamide N-oxide per mouse was administered, urinary excretion of nicotinamide, MNA, 2-Py, and 4-Py increased 6.4-, 1.8-, 1.6-, and 1.7-fold, respectively, compared with the control values. The increased ratios of MNA, 2-Py, and 4-Py were about 1/2 of those when 20 mg nicotinamide was administered, so the relative activity of nicotinamide N-oxide to nicotinamide as niacin is considered to be about 1/2. In conclusion, it was found the possibility that the reactions N′-methylnicotinamide → nicotinamide and nicotinamide N-oxide → nicotinamide occur, at least in mice, and that therefore N′-methylnicotinamide and nicotinamide N-oxide have niacin activity. 相似文献
11.
Hideo Ohkawa Yukiko Okihara Junshi Miyamoto 《Bioscience, biotechnology, and biochemistry》2013,77(6):1175-1182
On incubation with rat liver microsomes plus NADPH, Denmert (S-n-butyl S′-p-tert-butylbenzyl N-3-pyridyldithiocarbonimidate) underwent at least two different types of oxidation; hydroxylation and sulfoxidation. Hydroxylation of Denmert at the tert-butyl group was one of the major metabolic attacks in mammalian metabolism. Sulfoxidation of Denmert gave two isomers of Denmert sulfoxides which were intermediates in the metabolism and readily transformed into 2-(3′-pyridylimmo)-4-carboxylthiazolidine (HM) in the presence of l-cysteine without enzymatic mediation. This type of conjugation with cysteine appears to be a new class of metabolic reactions in mammals. Denmert S-oxide showed increased fungicidal activity when assayed in liquid cultures, but not on plant leaves. 相似文献
12.
Fukashi Horiuchi Keimei Fujimoto Toshiaki Ozaki Yoshihiko Nishizawa 《Bioscience, biotechnology, and biochemistry》2013,77(13):2003-2007
Several 3,5-dialkyl-4-hydroxybenzylidenemalononitriles and related compounds were tested for their fungicidal and acaricidal activities. The influence of structural variation on biological activity was studied by preparing and using a total of 22 compounds of benzylidenemalononitrile analogues.Amongst the compounds tested 3,5-di-tert-butyl and amyl-4-hydroxybenzylidenemalononitrile were most effective against fungus, Piricularia oryzae Car. and mite, Tetranychus telarius L. 相似文献
13.
Teruaki Mukaiyama Masashi Nagai Takafumi Matsutani Naoyuki Shimomura 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):17-30
Abstract Several β-d-ribonucleosides were synthesized in high yields under mild conditions by N-glycosylations of methyl 2,3,5-tri-O-benzoyl-β-d-ribofuranosyl carbonate (1) with trimethylsilylated nucleoside bases in acetonitrile using a catalytic amount of metal iodide such as SnI2, SbI3 or TeI4. A deprotection of N6 -benzoyl group of coupling product took place to a considerable extent when N6 -benzoyl-N6 , N9 -bis(trimethylsilyl)adenine was employed as a nucleoside base using SnI2 or SnCI2 as a catalyst while it was minimized when SbI3 or TeI4 was used. Further, the N-glycosylation of 1 with 7-trimethylsilyltheophylline in the presence of a catalytic amount of metal iodide was more effectively achieved in nitrile solvents other than acetonitrile. 相似文献
14.
Assaad A. Eid Ali Koubeissi Ribal Bou-Mjahed Nadine Al Khalil Manal Farah Rita Maalouf Niveen Nasser Kamal H. Bouhadir 《Bioorganic & medicinal chemistry letters》2013,23(1):174-178
The synthesis of a series of novel 3,4-cis- and 3,4-trans-substituted carbocyclic nucleoside analogs from protected uracil and thymine is described. The key reaction in the followed synthetic protocols utilized the Mitsunobu reaction to couple 3,4-substituted cyclopentanols to 3N-benzoyl uracil or 3N-benzoyl thymine. These molecules were evaluated with regard to their ability to treat diabetic nephropathy. Our results show that two analogs significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro and, more interestingly, exhibited an anti-oxidative effect suggesting that the activity may be mediated through ROS-dependent mechanism. 相似文献
15.
Delia Preti Riccardo Rondanin Barbara Cacciari Ernest Hamel Jan Balzarini 《Journal of enzyme inhibition and medicinal chemistry》2018,33(1):1225-1238
Inhibition of microtubule function using tubulin targeting agents has received growing attention in the last several decades. The indole scaffold has been recognized as an important scaffold in the design of novel compounds acting as antimitotic agents. Indole-based chalcones, in which one of the aryl rings was replaced by an indole, have been explored in the last few years for their anticancer potential in different cancer cell lines. Eighteen novel (3′,4′,5′-trimethoxyphenyl)-indolyl-propenone derivatives with general structure 9 were synthesized and evaluated for their antiproliferative activity against a panel of four different human cancer cell lines. The highest IC50 values were obtained against the human promyelocytic leukemia HL-60 cell line. This series of chalcone derivatives was characterized by the presence of a 2-alkoxycarbonyl indole ring as the second aryl system attached at the carbonyl of the 3-position of the 1-(3′,4′,5′-trimethoxyphenyl)-2-propen-1-one framework. The structure–activity relationship (SAR) of the indole-based chalcone derivatives was investigated by varying the position of the methoxy group, by the introduction of different substituents (hydrogen, methyl, ethyl or benzyl) at the N-1 position and by the activity differences between methoxycarbonyl and ethoxycarbonyl moieties at the 2-position of the indole nucleus. The antiproliferative activity data of the novel synthesized compounds revealed that generally N-substituted indole analogues exhibited considerably reduced potency as compared with their parent N-unsubstituted counterparts, demonstrating that the presence of a hydrogen on the indole nitrogen plays a decisive role in increasing antiproliferative activity. The results also revealed that the position of the methoxy group on the indole ring is a critical determinant of biological activity. Among the synthesized derivatives, compound 9e, containing the 2-methoxycarbonyl-6-methoxy-N-1H-indole moiety exhibited the highest antiproliferative activity, with IC50 values of 0.37, 0.16 and 0.17?μM against HeLa, HT29 and MCF-7 cancer cell lines, respectively, and with considerably lower activity against HL-60 cells (IC50: 18?μM). This derivative also displayed cytotoxic properties (IC50 values ~1?μM) in the human myeloid leukemia U-937 cell line overexpressing human Bcl-2 (U-937/Bcl-2) via cell cycle progression arrest at the G2-M phase and induction of apoptosis. The results obtained also demonstrated that the antiproliferative activity of this molecule is related to inhibition of tubulin polymerisation. The presence of a methoxy group at the C5- or C6-position of the indole nucleus, as well as the absence of substituents at the N-1-indole position, contributed to the optimal activity of the indole-propenone-3′,4′,5′-trimethoxyphenyl scaffold. 相似文献
16.
《Bioscience, biotechnology, and biochemistry》2013,77(8):1368-1370
Rhodanine (1), rhodanine-3-acetic acid (2), methylrhodanine (3), and aminorhodanine (4) inhibited the growth of plants. Among them, 4 was the strongest inhibitor of the roots of all the tested plants. On the other hand, N-acetylaminorhodanine (5) and N-benzoylaminorhodanine (6) greatly decreased the inhibitory activity. The results suggest that the free amino group at N-3 of 4 is essential to the greater inhibitory activity of rhodanine derivatives. The plant-growth inhibition of 1–6 is related to the chlorophyll content of the plant treated with them and their acute toxicities in mice. 相似文献
17.
Kinji Uchida 《Bioscience, biotechnology, and biochemistry》2013,77(2):561-563
Ninety-two thiolcarbamates with various substituents at the nitrogen and sulfur atoms, and their related compounds were synthesized, and their fungicidal activity against rice blast, Piricularia oryzae, and herbicidal activity against barnyardgrass, Echinochloa crus-galli, were determined in laboratory tests. The thiolcarbamate structure was necessary for the high fungicidal and herbicidal activities. The hydrophobicity of the substituents at the nitrogen atom was shown by the adaptive least-squares (ALS) method to be favorable to the fungicidal activity. The bulkier the substituents at the nitrogen atom, the less was the fungicidal activity. However, bulkiness of the substituents at the nitrogen and sulfur atoms was unfavorable to the herbicidal activity. The existence of a hydrogen atom at the nitrogen atom was favorable to fungicidal activity, but not to herbicidal activity. Correlation analyses were made to find compounds with both fungicidal and herbicidal activities against rice pests. 相似文献
18.
T. V. Tyrtysh N. E. Byramova N. V. Bovin 《Russian Journal of Bioorganic Chemistry》2000,26(6):414-418
3-O-Acetyl and 3-O-benzoyl derivatives of 1,6-anhydro-N-acetyl-β-D-glucosamine were synthesized via its selective tritylation followed by the 3-O-acylation and removal of the trityl protective group. Tritylium trifluoromethanesulfonate, which can easily be prepared by
mixing solutions of triphenylcarbinol and trimethylsilyl trifluoromethanesulfonate in an equimolar ratio, was suggested as
a reagent for the effective tritylation of a secondary hydroxyl group.
This paper is dedicated to the 70th birthday of Prof. A. Ya. Khorlin. 相似文献
19.
Xinwei Zhang Jun Fang Chenjie Li Jie Zhang Shuwen Yang Bin Deng Song Tu 《化学与生物多样性》2023,20(1):e202200971
Dimethomorph is a kind of cinnamamide fungicide with high fungicidal activities for oomycete diseases. The commercially available dimethomorph is a mixture of two isomers, in which (Z)-dimethomorph possessing higher activity and (E)-dimethomorph possessing lower activity. Herein, we reported the design, synthesis and fungicidal activities of a series of novel indole-modified cinnamamide derivatives, which used the indole group to ‘fix’ the cis-styrene group in (Z)-dimethomorph. The modification of the molecular structure of cinnamamide compounds could be beneficial to improve its practical application performance. Tested the fungicidal activities, it was found that compounds 8j , 9a , 9e , 9i and 9j showed excellent in vivo fungicidal activities (80–100 %) against Pseudoperonospora cubensis at a concentration of 100 mg L−1, while dimethomorph and flumorph were noneffective. Moreover, parts of synthesized indole-modified cinnamamide derivatives 8 ( 8a , 8c , 8d and 8j ) and 9 ( 9c and 9j ) exhibited the same in vivo fungicidal activities against Phytophthora infestans with dimethomorph or flumorph at a concentration of 50 mg L−1 with 100 % inhibition. The biological assay results indicated that indole-modified cinnamamide derivatives have promising applications in the prevention and treatment of Phytophthora infestans. 相似文献
20.
Various monosaccharides and oligosaccharides were used to define the specificity of theButea frondosa lectin using the hapten inhibition technique of human erythrocyte agglutination. AlthoughB. frondosa lectin exhibited higher affinity forN-acetylgalactosamine, lactose andN-acetyllactosamine appeared to be relatively good inhibitors of haemagglutination. The behaviour ofN-acetyllactosamine-type oligosaccharides and glycopeptides on a column ofB. frondosa lectin immobilized on Sepharose 4B showed that the sugar-binding specificity of the lectin is directed towards unmaskedN-acetyllactosamine sequences. Substitution of theseN-acetyllactosamine sequences by sialic acid residues completely abolished the affinity of the lectin for the saccharides. The presence of one or several Fuc(1-3)GlcNAc groups completely inhibited the interaction between the glycopeptides and the lectin. Substitution of the core -mannose residue by an additional bisecting (1-4)GlcNAc residue decreases the affinity of the lectin for these structures as compared with the unsubstituted ones. 相似文献