共查询到20条相似文献,搜索用时 31 毫秒
1.
Kang-Ping Xu Hui Zou Qiang Tan Fu-Shuang Li Jian-Feng Liu Hong-Lin Xiang 《Journal of Asian natural products research》2013,15(2):93-96
Selaginellins I (1) and J (2), two new compounds, were isolated from Selaginella tamariscina (Beauv.) Spring and were characterized as (R,S)-4-((2′,4′-dihydroxy-4-(hydroxymethyl)-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene)cyclohexa-2,5-dienone (1) and (R,S)-4-((3-((3,4-dihydroxyphenyl)ethynyl)-4′-hydroxy-4-(hydroxymethyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene)cyclohexa-2,5-dienone (2) on the basis of UV, IR, 1D and 2D NMR, and HR-ESI-MS spectroscopic analysis. 相似文献
2.
The new sesquiterpenoid (6R)-2-chloro-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (1), together with ten known compounds, (6R)-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (2), bauerenol acetate (3), lupenone (4), α-amyrenone (5), β-sitosterol (6), stigmasterol (7), β-amyrin (8), ursolic acid (9), betulinic acid (10), scopolin (11), have been isolated from the roots of Euphorbia chrysocoma Lévl. et Vant. Their structures have been elucidated by spectroscopic data. 相似文献
3.
目的研发一种新型唑烷酮类抗生素((3R,3a S)-7-(6-((S)3-甲基-2-唑烷酮-5-基)吡啶-3-基)-1-氧-1,3,3a,4-四氢苯并[b]唑[3,4-d][1,4]嗪-3-基)甲基)磷酸单酯(TJ1508)的合成工艺,并研究其晶型。方法以磷酸二苄酯中间体为原料,通过酸催化脱苄基得到TJ1508,在不同的溶剂体系中析晶得到不同晶型,采用粉末X射线衍射分析(PXRD)和差示扫描量热分析(DSC)对其进行表征,并对其进行加速稳定性试验和溶剂残留检测。结果目标化合物的收率最高为89%,得到3种不同的晶型A、B和C,稳定性、溶剂残留和钯残留均优于化合物专利无定型产品。结论设计了一种TJ1508的简易合成路线,得到3种稳定的晶型,其中晶型C最为稳定。 相似文献
4.
Chemical investigation of Trogopterus feces has led to the isolation of four new long-chain aliphatics, including two new fatty alcohols, 8,15-nonacosanediol (1) and 6,13-nonacosanediol (2), one new fatty acid ester, dihexyl 7,7′-oxydiheptanoate (3), and one new ceramide, (2R)-2-hydroxy-N-[(2S,3S,4R,11E)-1,3,4-trihydroxydocos-11-en-2-yl]heneicosanamide (4). Their structures were elucidated by means of chemical and extensive spectroscopic analysis. Compound 3 exhibited moderate activity of antithrombin in vitro. 相似文献
5.
Gui-Shan Tan Kang-Ping Xu Fu-Shuang Li Chen-Jing Wang Tuo-Ying Li Chang-Ping Hu 《Journal of Asian natural products research》2013,15(12):1001-1004
A novel compound, selaginellin C (1), was isolated from Selaginella pulvinata Maxim (Hook et Grev.) as (R,S)-4-((1,2-dihydroxyethyl)-2′,4′-dihydroxy-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)((4-hydroxyphenyl)methylene)cyclohexa-2,5-dienone, along with two known compounds, selaginellin (2) and selaginellin A (3). The structure of the new compound was elucidated on the basis of 1D and 2D NMR as well as HR-ESI-MS spectroscopic analysis. 相似文献
6.
Mariia Makarova Rodell C. Barrientos Oscar B. Torres Gary R. Matyas Arthur E. Jacobson Agnieszka Sulima Kenner C. Rice 《Journal of labelled compounds & radiopharmaceuticals》2020,63(13):564-571
A deuterated hapten was designed and synthesized that will be essential for a future study of residual hapten and stability of a hapten-protein conjugate. This hapten, 6-AmHap, was chosen for a heroin vaccine that is now slated for a Phase 1 clinical trial. A maleimide-thiol bioconjugation strategy was successfully applied to our heroin vaccine to connect the hapten 6-AmHap with an immunogenic carrier protein (tetanus toxoid, TT) through a trityl-protected 3-mercaptopropanamide linker. The antibodies induced by the vaccine have been found to have activity against several opioids, including heroin and its metabolites, and, importantly, leave alternate pain treatment medications such as methadone untouched. To the best of our knowledge, no other hapten for a heroin vaccine has been deuterated, yet this tool may prove to be of great importance in the study of residual hapten during product release and the long-term stability program of a hapten-protein conjugate as part of FDA regulatory requirements. Hydrocodone was the starting material for the synthesis of the deuterated 6-AmHap, with a stable amide at C6 and a 3-mercaptopropanamide linker attached at C3. The desired deuterated product was prepared as the disulfide, 3,3′-disulfanediylbis(N-((7S,7aR,12bS)-7-acetamido-3-[2H3]methyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl)propanamide), that could be easily reduced to form the needed hapten, N-((4aR,7S,7aR,12bS)-7-acetamido-3-[2H3]methyl]-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl)-3-mercaptopropanamide. 相似文献
7.
《Pharmaceutical biology》2013,51(5):584-588
Prasaplai is a Thai traditional medicine for relieving dysmenorrhea and adjusting the menstrual cycle. Three fatty acid esters, (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate (1), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate (2) and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (3) are formed during storage from the reaction of chemical components in two herbs, i.e., fatty acids in Nigella sativa (L.) (Ranunculaceae) and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-ol (compound D) in Zingiber cassumunar (Roxb.) (Zingiberaceae). The formations of these artifacts were monitored for 1 year and their amounts were analyzed by HPLC at certain periods of time. The results showed that artifact formation was saturated after 73 days of storage. The amount of each artifact in the saturation period ranged from 3.93?±?0.06 to 4.30?±?0.18% w/w for compound 1, 1.69?±?0.08 to 1.9?±?0.13% w/w for compound 2 and 0.09?±?0.003 to 0.1?±?0.005% w/w for compound 3. Cytotoxicity of the artifacts was evaluated using NCI-H187, KB, and BC cancer cell lines and found that the IC50 of all artifacts in all tests were higher than 20 μg/mL. For acute toxicity in mice, the LD50 of each artifact was more than 300?mg/kg. 相似文献
8.
Shiv Kumar Suchita Prasad Bipul Kumar Hemant K. Gautam Sunil K. Sharma 《Medicinal chemistry research》2016,25(6):1057-1073
A series of thirty-three novel triazolyl pyranochromen-2(1H)-one derivatives have been synthesized via Cu (I) catalysed Huisgen 1,3-dipolar cycloaddition reaction. All of the synthesized compounds have been fully characterized from their spectral data and evaluated for antibacterial activity against both gram-positive and gram-negative bacteria. The activity results revealed that amongst all the compounds screened, six compounds, i.e. 2-[4-(((7-ethyl-2,2,6-trimethyl-8-oxo-2,3,4,8-tetrahydropyrano[3,2-g]chromen-10-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl]acetic acid (41), 10-[(1-(1,3-dihydroxypropan-2-yl)-1H-1,2,3-triazol-4-yl)methoxy]-3-ethyl-4,8,8-trimethyl-7,8-dihydropyrano[3,2-g]chromen-2(6H)-one (44), 3-ethyl-4,8,8-trimethyl-10-[(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methoxy]-7,8-dihydropyrano[3,2-g]chromen-2(6H)-one (46), 2-[4-(((7-hexyl-2,2,6-trimethyl-8-oxo-2,3,4,8-tetrahydropyrano[3,2-g]chromen-10-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl]acetic acid (52), 10-[(1-(1,3-dihydroxypropan-2-yl)-1H-1,2,3-triazol-4-yl)methoxy]-3-hexyl-4,8,8-trimethyl-7,8-dihydropyrano[3,2-g]chromen-2(6H)-one (55) and 3-hexyl-4,8,8-trimethyl-10-[(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methoxy]-7,8-dihydropyrano[3,2-g]chromen-2(6H)-one (57), exhibited moderate activity against all the strains studied with zone of inhibition between 10 and 16 mm and MIC values in the range of 75–170 µg/mL as compared to the standard used. The information obtained from structure–activity relationship can be used to design and develop the next generation of compounds with higher antibacterial efficacy. 相似文献
9.
Hao-Fu Dai Jun Liu Zhuang Han Yan-Bo Zeng Hui Wang 《Journal of Asian natural products research》2013,15(2):134-137
Two new 2-(2-phenylethyl)chromones, (5S *,6R *,7S *)-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (1) and (5S *,6R *,7R *)-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (2), were isolated from the Chinese eaglewood of Aquilaria sinensis (Lour.) Gilg. Their structures were established by detailed MS and NMR spectroscopic analysis, as well as comparison with the literature data. 相似文献
10.
Dan Zhang An-Jun Deng Lin Ma Zhi-Hong Li Zhi-Hui Zhang Jian-Dong Jiang 《Journal of Asian natural products research》2016,18(3):260-267
Two new compounds of phenylpropanoids, (S)-N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-5-oxopyrrolidine-2-carboxamide (1) and (3R)-3-O-β-d-glucopyranosyl-3-phenylpropanoic acid (2), were isolated from the stems of Ephedra sinica. Their structures were elucidated by in-depth examination of spectroscopic data, mainly including those from the 1D and 2D NMR and HRESIMS techniques, and chemical method. The absolute configurations of the two compounds were also corroborated through CD procedure. 相似文献
11.
Guo-Ru Shi Xin Wang Yan-Fei Liu Chun-Lei Zhang Yan Wang Li Li 《Journal of Asian natural products research》2016,18(10):921-927
Phytochemical investigation on the whole plants of Iris japonica led to the isolation of four new aromatic glycosides. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as (?)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (1), (?)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (2), (?)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (3), (?)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (4), respectively. 相似文献
12.
Hydrolysis of oleoside-type secoiridoid glucosides, oleuropein (1) and ligustroside (2), in the presence of β-glucosidase provided their aglycones, named (5S,8R,9S)-7-3,4-dihydroxyphenethyl elenolate (3) and (5S,8R,9S)-7-4-hydroxyphenethyl elenolate (4), respectively. The structures of 3 and 4 were identified by spectroscopic means and optical rotation measurements. Evaluation of the cytotoxic and epidermal growth
factor receptor (EGFR) tyrosine kinase inhibitory activities of compounds 1–4 showed that compounds 3 and 4 exhibited moderate cytotoxicity against a disease-oriented panel of 39 human cancer cell lines in vitro, whereas compound
3 inhibited the enzyme. 相似文献
13.
Ting Chen Yong-Jun Kan Cheng-Gang Zhang 《Journal of Asian natural products research》2013,15(12):1101-1107
AbstractA new highly oxygenated pregnane steroid, pregn-7-ene-2β,3α,15α,20-tetrol (1) and two new 5-hydroxymethylfurfural derivatives, (5-formylfuran-2-yl)methyl 2-hydroxypropanoate (2) and (5-formylfuran-2-yl)methyl 2-(4-hydroxyphenyl)acetate (3), together with four known compounds, were isolated from the water decoction of Poria cocos. Their structures were established on the basis of extensive spectroscopic analysis. Compound 1 showed moderate inhibitory activity and a known compound (3S,6S)-3-[(1R)-1-hydroxyethyl]-6-(phenylmethyl)-2,5-piperazinedione (5) showed weak inhibitory activity against α-glucosidase, respectively. 相似文献
14.
Oksana Mikhalchenko Irina Il’ina Alla Pavlova Ekaterina Morozova Dina Korchagina Tat’yana Tolstikova Evgeny Pokushalov Konstantin Volcho Nariman Salakhutdinov 《Medicinal chemistry research》2013,22(6):3026-3034
A set of new heterocyclic compounds with different types of framework, including a new type of framework, were synthesized by reactions of verbenol epoxide and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aromatic aldehydes containing three methoxy groups. The analgesic activity of these substances was studied. Three compounds possessed considerable activity in vivo in the acetic acid-induced writhing test. (2S,4R,4aR,8S,8aR)-4,7-Dimethyl-2-(2,4,5-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-4,8-epoxychromene exhibited high analgesic activity in both acetic acid-induced writhing and hot plate tests; its selectivity index IS50 exceeded 60. 相似文献
15.
Yu Luo Ling Qiu Yun Deng Xiao-Hong Yuan Ping Gao 《Journal of Asian natural products research》2013,15(9):883-888
AbstractA new chromone and a new aliphatic ester were isolated from the EtOAc extract of myceliums of Daldinia eschscholtzii. Their structures were elucidated as (R)-5-hydroxy-8-methoxy-2-methylchroman-4-one (1) and (E)-6-(non-3-en-1-yl) -2H-pyran-2-one (2) by interpretation of the spectroscopic evidence. 相似文献
16.
The heterocyclic analogues of chalcones were synthesized by Claisen Schmidt reaction of (a) benzaldehyde with 2-acetylfurane, 2-acetylpyrrole and 2-acetylthiophene and (b) acetophenone with furfural, thiophene-2-carbaldehyde and pyrrole-2-carbaldehyde. The photolysis of class (a) and (b) chalcones under UV lamp gave different products. The stereoselective photodimerization of 1-(furane-2-yl)-3-phenylprop-2-en-1-one (1), 3-phenyl-1-(1H-pyrrole-2-yl)-prop-2-en-1-one (2) gave β-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (furane-2-yl methanone) (7), (3,4-diphenylcyclobutane-1,2-diyl)bis ((1H-pyrrol-2-yl) methanone) (8) by syn head-to-head coupling whereas 3-phenyl-1-(thiophen-2-yl)-prop-2-en-1-one (3) gave δ-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (thiophen-2-yl methanone) (9) by anti head-to-head coupling. The photolytic products of 3-(furane-2-yl)-1-phenylprop-2-en-1-one (4), 1-phenyl-3-(thiophen-2-yl)-prop-2-en-1-one (5) and 1-phenyl-3-(1H-pyrrole-2-yl)- prop-2-en-1-one (6) were identified as corresponding 1,6-di(furane-2-yl)-3,4-diphenylhexa-1,5-diene-3,4-diol (10), 3,4-diphenyl-1,6-di(thiophen-2-yl)hexa-1,5-diene-3,4-diol (11) and 3,4-diphenyl-1,6-di(1H-pyrrol-2-yl)hexa-1,5-diene-3,4-diol (12) pinacol dimers. The antibacterial and antifungal activity of the precursor chalcones and the dimeric products showed antimicrobial activities of different extents with respect to individual compounds. In general, photolysis of heteroaryl chalcones causes the depletion of antimicrobial activity. 相似文献
17.
Irina Il’ina Oksana Mikhalchenko Alla Pavlova Dina Korchagina Tat’yana Tolstikova Konstantin Volcho Nariman Salakhutdinov Evgeniy Pokushalov 《Medicinal chemistry research》2014,23(12):5063-5073
New chiral heterocyclic compounds with a hexahydro-2H-chromene framework were synthesized by reactions of (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aromatic aldehydes in the presence of montmorillonite clay. The analgesic activity of the compounds was studied in vivo. The majority of these compounds showed significant analgesic activity in the acetic acid-induced writhing test; the compounds containing one hydroxy and one methoxy substituents also showed analgesic activity in the hot-plate test. (2S,4aR,8R,8aR)-2-(3-Hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol was as effective as the diclofenac sodium reference taken in the same dose in both tests. It has low acute toxicity and is very promising for further development. 相似文献
18.
Abstract
A series of 6-substituted 2-[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (5, 6) and 2,4-bis[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (9, 10) were designed, synthesized, and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. The synthesis of these compounds involved the Reformatsky-type reaction between ethyl α-(bromomethyl)acrylate and the proper ketones. Among these compounds, 2-[(4-methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione (5a) is the most active compound and shown the selective inhibition activity against Proteus vulgaris. 相似文献19.
Caterina Porcelli Johanna Kreissl Martin Steinhaus 《Journal of labelled compounds & radiopharmaceuticals》2020,63(11):476-481
For the accurate and sensitive quantitation of the off-flavor compound geosmin, particularly in complex matrices, a stable isotopologue as internal standard is highly advantageous. In this work, we present a versatile synthetic strategy leading from (4aR)-1,4a-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one to tri-deuterated (–)-geosmin ((4S,4aS,8aR)-4,8a-dimethyl(3,3,4-2H3)octahydronaphthalen-4a(2H)-ol). The starting material was readily accessible from inexpensive 2-methylcyclohexan-1-one using previously published procedures. 相似文献
20.
Hamid-Reza Adhami Johannes Lutz Hanspeter K?hlig Martin Zehl Liselotte Krenn 《Scientia pharmaceutica》2013,81(3):793-805
The use of herbal medicinal preparations in dementia therapy has been studied based on experience from traditional medicine. A dichloromethane extract of gum ammoniacum, the gum-resin from Dorema ammoniacum D. Don had shown acetylcholinesterase (AChE) inhibitory activity in a previous study. The aim of this study was the isolation and characterization of the active compounds from this resin. The extract was investigated by a respective colorimetric microplate assay and the active zones were identified via TLC bioautography and isolated using several chromatographic techniques. The structures of the active components were characterized by one- and two-dimensional 1H and 13C NMR spectroscopy and mass spectrometry as (2′S,5′S)-2′-ethenyl-5′-(3-hy-droxy-6-methyl-4-oxohept-5-en-2-yl)-7-methoxy-2′-methyl-4H-spiro[chromene-3,1′-cyclopentane]-2,4-dione (1), which is an analogue of doremone A and a new natural compound, and as (2′S,5′R)-2′-ethenyl-5′-[(2R,4R)-4-hydroxy-6-methyl-3-oxohept-5-en-2-yl]-7-methoxy-2′-methyl-4H-spiro[chromene-3,1′-cyclo-pentane]-2,4-dione (2 = doremone A), (4E,8E)-1-(2,4-dihydroxyphenyl)-5,9,13-trimethyltetradeca-4,8,12-trien-1-one (3 = dshamirone), and 4,7-dihydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2H-chromen-2-one (4 = am-moresinol). Dshamirone turned out to be the most active compound with an IC50 value for AChE inhibitory activity of 23.5 μM, whereas the other substances showed weak activity. The concentrations of the analytes in the resin were determined by HPLC as 3.1%, 4.6%, 1.9%, and 9.9%, respectively. 相似文献