共查询到20条相似文献,搜索用时 15 毫秒
1.
Asami T Min YK Nakano T Matsuyama T Murofushi N Yamaguchi I Yoshida S 《Bioorganic & medicinal chemistry letters》2000,10(14):1571-1574
Replacing the 4'-carbonyl group of abscisic acid with a methoxy group does not affect the abscisic acid (ABA)-like activities of the product in barley aleurone protoplasts, although the reduction of ABA to 4'-hydroxyl derivatives significantly reduces the ABA-like activity of the products. This suggests that methoxy derivatives of abscisic acid might be used to produce probes for ABA binding proteins. 相似文献
2.
Stanton JL Cahill E Dotson R Tan J Tomaselli HC Wasvary JM Stephan ZF Steele RE 《Bioorganic & medicinal chemistry letters》2000,10(15):1661-1663
The synthesis of substituted phenoxyphenyl oxamic acid derivatives related to L-thyronine (L-T3) is described. The in vitro and in vivo cholesterol lowering and cardiovascular effects of these compounds are presented and discussed. 相似文献
3.
Lei Shi Xiu E Feng Jing Rong Cui Lian Hua Fang Guan Hua Du Qing Shan Li 《Bioorganic & medicinal chemistry letters》2010,20(18):5466-5468
A series of new flavanone derivatives of farrerol was synthesized by a convenient method. The in vitro anti-tumor activity of these compounds was evaluated against human Bel-7402, HL-60, BGC-823 and KB cell lines, the protein tyrosine kinase (PTK) inhibitor activity was also tested. Their cytoprotective activity was tested using hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells. Their in vitro anti-atherosclerosis activity was tested on vascular smooth muscle cells by the MTT method using tetrandrine as a positive contrast drug. The structures of all compounds synthesized were confirmed by 1H, 13C NMR and ESI-MS. Most of the compounds exhibited good pharmacological activity and the preliminary structure–activity relationships were described. 相似文献
4.
Miersch J Grancharov K Pajpanova T Tabakova S Stoev S Krauss GJ Golovinsky E 《Amino acids》2000,18(1):41-59
Summary. The canavanine derivatives L-canavanine hydrazide (CH), L-canavanine-bis-(2-chloroethyl)hydrazide (CBCH) and L-canavanine
phenylhydrazide (CPH) were synthesized and evaluated for biological activity in microorganisms, plants and tumor cells using
canavanine as a positive control. (1) In microbial systems, the compounds exerted activity, as assessed in 14 bacterial strains.
The effect of canavanine was easily removed by equimolar concentrations of arginine or ornithine, while the effect of CBCH
or CPH was abolished by 10-fold excess of arginine or 10- to 100-fold excess of ornithine. (2) In plants, the activity of
CH and CBCH were relatively low, whereas the inhibitory potential of CPH was comparable or even superior to that of canavanine,
resulting at 1 mM concentration in a nearly complete block of tomato cell growth, and reducing by up to 80% the length of
radicles of cress, amaranth, cabbage and pumpkin. (3) In pumpkin seeds, CPH or canavanine induced the synthesis of four small
heat shock proteins of hsp-17 family in the pH range of 6 to 7.5. The proteins exhibited in both cases a similar profile,
but differed in the timing of their expression and/or accumulation. With canavanine, the highest hsp-17 expression was found
after 48 h of drug treatment, while with CPH this maximum was shifted to 24 h. (4) CPH proved to be highly cytotoxic against
Friend leukemia cells in culture, exceeding by one order of magnitude the cytotoxicity of canavanine. The effect of canavanine
was completely removed in the presence of equimolar amounts of arginine, while a 20-fold excess of arginine failed to abolish
the cytotoxicity of CPH. Thus, a proper hydrazide modification of canavanine may lead to a significant increase in its growth-inhibitory
activity and to a change in the mode of action of the parent compound.
Received October 5, 1999, Accepted January 27, 1999 相似文献
5.
Zhen Li Van H. Tran Michelle C.H. Ng Colin C. Duke 《Chemistry and physics of lipids》2009,158(1):39-2461
Allylic hydroxylated derivatives of the C18 unsaturated fatty acids were prepared from linoleic acid (LA) and conjugated linoleic acids (CLAs). The reaction of LA methyl ester with selenium dioxide (SeO2) gave mono-hydroxylated derivatives, 13-hydroxy-9Z,11E-octadecadienoic acid, 13-hydroxy-9E,11E-octadecadienoic acid, 9-hydroxy-10E,12Z-octadecadienoic acid and 9-hydroxy-10E,12E-octadecadienoic acid methyl esters. In contrast, the reaction of CLA methyl ester with SeO2 gave di-hydroxylated derivatives as novel products including, erythro-12,13-dihydroxy-10E-octadecenoic acid, erythro-11,12-dihydroxy-9E-octadecenoic acid, erythro-10,11-dihydroxy-12E-octadecenoic acid and erythro-9,10-dihydroxy-11E-octadecenoic acid methyl esters. These products were purified by normal-phase short column vacuum chromatography followed by high-performance liquid chromatography (HPLC). Their chemical structures were characterized by liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR). The allylic hydroxylated derivatives of LA and CLA exhibited moderate in vitro cytotoxicity against a panel of human cancer cell lines including chronic myelogenous leukemia K562, myeloma RPMI8226, hepatocellular carcinoma HepG2 and breast adenocarcinoma MCF-7 cells (IC50 10-75 μM). The allylic hydroxylated derivatives of LA and CLA also showed toxicity to brine shrimp with LD50 values in the range of 2.30-13.8 μM. However these compounds showed insignificant toxicity to honeybee at doses up to 100 μg/bee. 相似文献
6.
Moody DL Dyba M Kosakowska-Cholody T Tarasova NI Michejda CJ 《Bioorganic & medicinal chemistry letters》2007,17(8):2380-2384
Novel 5-aza-ellipticine derivatives were synthesized and tested as antitumor agents. The new compounds were prepared more readily than the analogous ellipticine derivatives, which are known to be potent anti-tumor agents Although the novel 5-aza-ellipticine derivatives are not as biologically active as their corresponding ellipticine analogues, the new compounds represent a new, readily accessible class of heteroaromatic catalytic inhibitors of topoisomerase II and possible anti-tumor agents. 相似文献
7.
Ohshita K Ishiyama H Takahashi Y Ito J Mikami Y Kobayashi J 《Bioorganic & medicinal chemistry》2007,15(14):4910-4916
A series of stereoisomers for the azetidine ring of penaresidin B was synthesized and their cytotoxic and antimicrobial activities were evaluated. Among six synthetic isomers 1-6, isomers 4 and 5 showed relatively potent cytotoxic activity against A549 (lung) and HT29 (colon) tumor cells as well as antibacterial activity. 相似文献
8.
V V Belakhov A A Levina Iu D Shenin B I Ionin L I Shatik M B Za?tseva G E Grinberg E B Shtil'bans L A Rachkovskaia 《Antibiotiki i khimioterapii͡a》1990,35(8):31-35
Reactions of levorin, a polyenic macrolide antibiotic, with aromatic aldehydes and hypophosphorous acid resulted in formation of its amino phenylphosphonium derivatives. Physicochemical and biological properties of the derivatives were studied. The levorin amino phenylphosphonium derivatives were shown to be low toxic and have antifungal and antiviral activities. 相似文献
9.
Coggiola B Pagliai F Allegrone G Genazzani AA Tron GC 《Bioorganic & medicinal chemistry letters》2005,15(15):3551-3554
A series of chimeric compounds bearing the combretastatin and the nitrogen mustard cores were synthesized. All the compounds were cytotoxic and inhibited tubulin polymerization. When combretastatin was joined to chlorambucil via an ester linkage, the resultant compound proved to be significantly more potent than the two compounds put together. When combretastatin was joined to nitrogen mustard via an ether linkage or when a true hybrid was synthesized, loss of potency was observed. Nonetheless, these latter compounds appeared to be more efficacious and surprisingly were able to inhibit tubulin depolymerization at high concentrations. 相似文献
10.
Sastry BS Suresh Babu K Hari Babu T Chandrasekhar S Srinivas PV Saxena AK Madhusudana Rao J 《Bioorganic & medicinal chemistry letters》2006,16(16):4391-4394
Nimbolide (1), a limonoid isolated from Azadirachta indica, is the chief cytotoxic principle in Neem leaves extract. Using nimbolide as a lead compound for anti-cancer analogue design, a series of nimbolide derivatives have been synthesized and evaluated for in vitro cytotoxic activity against a panel of human cancer cell lines. Out of 10 compounds screened 2g, 2h and 2i showed potent activity. 相似文献
11.
The synthesis of new acrylate and methacrylate derivatives of a glyphosate is reported. Two isomers resulting from a hindered rotation around the amide C--N bond are observed for both acrylic and methacrylic analogs, and barriers for internal rotation are obtained. Biological activity tests indicate that functionalized glyphosates possess herbicidal activity similar to that of the parent compound. Only the acrylated glyphosate derivatives undergo photopolymerization. The resulting photopolymer of acrylated glyphosate retains the biological activity. The methacrylated glyphosates are unreactive. Differential reactivity is explained by the different conformational preferences of the functionalized glyphosates. The experimental findings are supported by the results of density functional theory geometry optimizations. 相似文献
12.
Hadj-Bouazza A Teste K Colombeau L Chaleix V Zerrouki R Kraemer M Sainte Catherine O 《Nucleosides, nucleotides & nucleic acids》2008,27(5):439-448
The synthesis and biological activity of a novel DNA cross-linking antitumor agent is presented. The new alkylating agent significantly inhibited cell proliferation, migration and invasion as tested in vitro on the A431 vulvar epidermal carcinoma cell line. 相似文献
13.
Di Giacomo B Bedini A Spadoni G Tarzia G Fraschini F Pannacci M Lucini V 《Bioorganic & medicinal chemistry》2007,15(13):4643-4650
A new series of melatonin (MLT) dimers were obtained by linking together two melatonin units with a linear alkyl chain through the MLT acetamido group or through a C-2 carboxyalkyl function. The binding properties of these ligands were evaluated in in vivo experiments on cloned human MT(1) and MT(2) receptors expressed in NIH3T3 rat fibroblast cells. The class of 2-carboxyalkyl dimers was the most interesting one with compounds having good MT(1)/MT(2) nanomolar affinity. The data obtained suggest that the spacer length is crucial for optimal interaction at both receptor subtypes as well as to determine functional activity of the resulting dimers. 相似文献
14.
Synthesis and anti-HIV activity of oleanolic acid derivatives 总被引:4,自引:0,他引:4
Yong-Ming Zhu Jing-Kang Shen Hui-Kang Wang L. Mark Cosentino Kuo-Hsiung Lee 《Bioorganic & medicinal chemistry letters》2001,11(24):245-3118
Thirteen oleanolic acid derivatives were prepared and evaluated for anti-HIV activity in H9 lymphocytes. Saturating the C12–C13 double bond and converting the C17-carboxyl group to an aminomethyl group led to compounds 13– 15 and 19– 20, respectively, which showed improved anti-HIV activity. Compound 15 was the most potent derivative with EC50=0.0039 μg/mL and TI=3570. 相似文献
15.
Glycyrrhetinic acid (GA) is one of many interesting triterpenoic acids showing anticancerogenic potential. GA is known to trigger apoptosis in tumour cell lines, although GA has a low cytotoxicity. In our study we were able to prepare derivatives of GA that show lowered the IC(50) values as determined by a sulforhodamine B (SRB) assay using 15 different human tumour cell lines. Thus, combining an ester group combined with the presence of an amino acid moiety led to a ca. 60-fold improved antitumor activity. Experiments on mouse embryonic fibroblasts (NiH3T3) revealed that these compounds showed a better selectivity for tumour cells compared to the parent compound GA. An apoptotic effect of some of these compounds was determined using an acridine orange/ethidium bromide (AO/EB) test and DNA laddering experiments. 相似文献
16.
16 ABA esters including 11 new compounds were prepared by two different esterification routes. All the structures of ABA esters were confirmed by 1H NMR, 13C NMR and HRMS. Their biological activity and hydrolysis stability were investigated. Fortunately, there were 15 and 9 compounds which displayed much better or nearly the same inhibition activity for rice seedling growth and Arabidopsis thaliana seed germination compared to ABA, respectively. Especially, compounds 2d and 2g showed better biological activities than ABA in the three tests. Moreover, we found that chemical hydrolysis ability of the esters in vitro had little relationship to their biological activity. 相似文献
17.
D Poirier C Labrie Y Mérand F Labrie 《The Journal of steroid biochemistry and molecular biology》1991,38(6):759-774
Seven estradiol (E2) derivatives with an alkynylamide side chain at the 17 alpha position were synthesized starting from ethynylestradiol (EE2). The main chemical step was the coupling reaction of the acetylide ion of EE2 with carbon dioxide, glutaric anhydride or bromoalkyl ortho ester. The synthesis of these compounds is fast (3-6 steps according to the compound) and is easily achieved with good yield. Five compounds with different side chain lengths were evaluated for uterotrophic and antiuterotrophic activity in the CD-1 mouse. None of the tested compounds shows estrogenic activity in this sensitive in vivo system. At low doses (1 and 3 micrograms), a 14-57% inhibition of E2-induced uterine growth was observed while no additional inhibition was observed at the 10, 20 and 30 micrograms doses. In human breast carcinoma cells in culture, all compounds show estrogenic activity at high concentrations while only compound 39 (N-butyl,N-methyl-8-[3',17' beta-dihydroxy estra-1',3',5'(10')-trien-17' alpha-yl]-7-octynamide) possesses antiproliferative or antiestrogenic effects. No significant correlation could be demonstrated between alkynylamide side chain length and estrogenic or antiestrogenic activity. Among the compounds tested, the derivative of EE2 possessing a five-methylene (CH2) side chain (compound 39) possesses the best antiestrogenic activity (44 +/- 7% in the CD-1 mouse uterus assay at the 3 micrograms dose and 57 +/- 4% at 0.1 nM in human ZR-75-1 cancer cells in culture. 相似文献
18.
Mochizuki T Iwano Y Shiozaki M Kurakata S Kanai S Nishijima M 《Carbohydrate research》2000,324(4):225-230
The synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing part of the disaccharide instead of the phosphate group in lipid A, is described. One of the compounds thus synthesized, which has an acyl substitution pattern similar to that of Escherichia coli lipid A, showed lipopolysaccharide (LPS)-agonistic activity. The other, which contains four lipid chains in the molecule, exhibited strong LPS-antagonistic activity toward human monoblastic U937 cells. 相似文献
19.
Amal S. Yanni 《Russian Journal of Bioorganic Chemistry》2014,40(3):350-351
Aromatic aldazines with thiocyanates in glacial acetic acid produce corresponding bistriazolidine derivatives via criss-cross cycloaddition reaction. The chemical structure was confirmed by elemental and spectral analysis. Biological activity against some microorganisms was tested. 相似文献
20.
Madhavan GR Chakrabarti R Vikramadithyan RK Mamidi RN Balraju V Rajesh BM Misra P Kumar SK Lohray BB Lohray VB Rajagopalan R 《Bioorganic & medicinal chemistry》2002,10(8):2671-2680
A series of pyrimidinone derivatives of thiazolidinediones were synthesized. Their biological activity were evaluated in insulin resistant, hyperglycemic and obese db/db mice. In vitro PPARgamma transactivation assay was performed in HEK 293T cells. PMT13 showed the best biological activity in this series. PMT13 (5-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenylmethyl]thiazolidine-2,4-dione) showed better plasma glucose, triglyceride and insulin-lowering activity in db/db mice than rosiglitazone and pioglitazone. PMT13 showed better PPARgamma transactivation than the standard compounds. Pharmacokinetic study in Wistar rats showed good systemic exposure of PMT13. Twenty-eight day oral toxicity study in Wistar rats did not show any treatment-related adverse effects. 相似文献