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Dibutyltin(IV) oxide reacts with the cantharidin analogue, 4′-(7-oxabicyclo [2,2,1]-5-heptane-2,3-dicarboximide) benzoic acid, A, to give the complexes [(p-C8H8NO3-C6H4-COOBu2Sn)2O]2 (1) and (p-C8H8NO3-C6H4-COO)2SnBu2 (2) which had been characterized by IR and 1H, 13C, 119Sn NMR. Single X-ray crystal structure analysis has been determined for compound (1), which was analogue to most other [(RCOOBu2Sn)2O]2. The dimer features central of Bu4Sn2O2 unit with the two Bu2Sn groups being linked via bridging oxygen atom. Each tin atom adopts distorted trigonal bipyramidal structures via two carbons from a dibutyl moiety and three oxygen atoms from cantharidin derivative and bridging oxygen atom. In vitro tests show compounds 1 and 2 exhibit high cytotoxicity against P388 and HL-60. 相似文献
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The recently described pressure reaction in the presence of trithylamine with subsequent thermal (200°C) cyclization provided 13N‐pyridylcantharidinimides 4a‐4m from aminopyridines and cantharidin in yields of 15–83%. 2‐Amino‐3,5‐dichloropyridine failed to yield 4n . 相似文献
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Characterization of Novel Aminobenzylcantharidinimides and Related Imides by Proton NMR Spectra and Their Effects on NO Induction 下载免费PDF全文
Ing‐Jy Tseng Pen‐Yuan Lin Shiow‐Yunn Sheu Wan‐Ni Tung Ching‐Tung Lin Mei‐Hsiang Lin 《中国化学会会志》2015,62(1):59-63
Various acidic anhydrides including cantharidin were converted into corresponding aminobenzylcantharidinimide 3a and analogous imides 3b~k (at the ortho, meta, and para positions) with 35%~87% yields by reacting with aminobenzylamines and triethylamine. The two methyl side chains of cantharidinimides 3ao , 3am , and 3ap, and related imides had more than two chiral centers; the lone pair of electrons of nitrogen displayed a different chemical shift and coupling constant in H‐NMR spectra when the amino group of benzylamine was in the ortho position. These cantharidinimides had parent aniline, pyridine, and naphthalene plane structures, and the primary amine nucleophilicity and basicity might reflect the inductive electron’s negative effect on chemical shifts. We prepared cantharidinimides by heating the reactants cantharidin 1a , aliphatic and aromatic acid anhydrides, primary benzylic amines, and aniline derivatives to ca. 200 °C with 3 mL of dry toluene, and 1~2 mL of triethylamine in high‐pressure sealed tubes (Buchi glasuster 0032) to produce cantharidinimides and their analogues in good yields. The para‐aminobenzylic imides showed greater inhibition of nitric oxide (NO) synthesis by NO synthase (NOS) than did ortho‐ and meta‐aminobenzylic imides. Compound 3fp , para‐aminobenzylic norbonane‐imide, had the most potent effect on inducible NOS among the tested compounds and showed 35% inhibition. 相似文献
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Anna Rudo Hans‐Ullrich Siehl Klaus‐Peter Zeller Stefan Berger Dieter Sicker 《Chemie in Unserer Zeit》2013,47(5):310-316
Cantharidin was extracted from dried Spanish Flys (Lytta vesicatoria) and purified by sublimation. All analytical spectra were recorded and are reproduced either in the main part or in the supporting information. The NMR‐ and mass‐spectra have been interpreted and compared with theoretical calculations of the 13C chemical shifts. The project is a follow up of the recent book “Classics in Spectroscopy” by S. Berger and D. Sicker (Wiley‐VCH 2009). 相似文献
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Yaobo Zeng Yanlei Guo Yi Zhang Xianying Wang Yao Jiang Dajian Yang 《Biomedical chromatography : BMC》2020,34(6):e4801
We evaluated the protective effect and toxicity of extracts from Mylabris phalerata Pallas by measuring the activated partial thromboplastin time, prothrombin time, venous thrombosis and acute toxicity in rats. Results showed the petroleum ether and water fractions of M. phalerata inhibited thrombosis but hardly prolonged the activated partial thromboplastin time and prothrombin time in rats. The trichloromethane fraction had obvious toxicity with an LD50 of 0.2 g/kg in vivo, and contained many cantharidin analogs (CAs) by ultra-performance liquid chromatography–quadrupole ion trap–tandem mass spectrometry (UPLC–QTRAP–MS/MS). CAs are the major potential bioactivity constituent in M. phalerata. An effective and reliable UPLC–QTRAP–MS/MS method was successfully developed to separate and identify CAs. The fragmentation patterns of five purified compounds were applied to elucidate the structure of their analogs. Thirty-four CAs were characterized or tentatively identified, eight of which are proposed to be novel compounds ( 13 – 17 , 20 , 21 , 23 ), and their fragmentation patterns were investigated for the first time. Most importantly, a rapid and reliable UPLC–MS method was developed to identify the CAs of M. phalerata. This method has contributed to the discovery of most of these unknown analogs or their metabolites in M. phalerata effectively and quickly, and does not rely on limited chemical structural diversity libraries. 相似文献
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The new cantharidinimides 3a-j were prepared, in good to excellent yield, by heating the reactents 1 and 2a-j to 200 °C with toluene and triethylamine in a high pressure tube. The mixture was evaporated to dryness and furthermore heated to 180 °C-200 °C for 1 h. 相似文献
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选择有机磷基团对斑蝥素的结构骨架进行修饰改造,以外式双环[2.2.1]庚-5-烯-2,3-二甲酸酐为原料,设计合成了一系列斑蝥素类似物。化合物的结构经1HNMR,MS及元素分析确证。 相似文献
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Fritz Eiden 《Chemie in Unserer Zeit》2006,40(1):12-19
Numerous species of blister beetles use cantharidin in their blood as a protecting and attracting agent. From antiquity to the 20th century these beetles (and later the substance cantharidin itself) have been utilized as a medicine and an aphrodisiac. The advantages were however very limited, because of cantharidins high toxicity. From the first isolation of the active substance to the unravelling of its structure and the discovery of viable synthetic methods it took 150 years. Cantharidin has recently found growing interest among molecular biologists, pharmacologists and chemists, due to its property of inhibiting enzymes (protein phosphatases) which regulate cellular metabolism. 相似文献
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