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1.
Two New Antibacterial Chromeno[3,2-c]Pyridine Alkaloids from Whole Plants of Thalictrum scabrifolium
Yin Geng-Yun Zhu Ya-Ning Wu Fan Mi Qi-Li Shi Jian-Quan Gao Qian Zhu Ling-Chao Zhou Tao Li Jing Liu Xin Yang Guang-Yu Hu Qiu-Fen Kong Wei-Song 《Chemistry of Natural Compounds》2022,58(3):506-510
Chemistry of Natural Compounds - Two new chromeno[3,2-c]pyridine alkaloids, 9-acetyl-7-methoxy-3-methyl-10H-chromeno[3,2-c]pyridin- 10-one (1) and... 相似文献
2.
Isaka K Nagatsu A Ondognii P Zevgeegiin O Gombosurengyin P Davgiin K Kojima K Ogihara Y 《Chemical & pharmaceutical bulletin》2001,49(9):1072-1076
Nine novel prenyl-dihydrofurocoumarin-type sesquiterpenoid derivatives, 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E)-pentenyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4-methyl-5- (4-methyl-2-furyl)-3(E)-pentenyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-methoxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo-[3,2-c]coumarin, and 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E)-pentenyl]-furo[3,2-c]coumarin, were isolated from the roots of Ferula ferulaeoides [corrected]. The structures were established by comprehensive spectral analysis. The biosynthetic pathway leading to these prenyl-furocoumarin-type sesquiterpenoids is proposed based on their structures. 相似文献
3.
We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H(2)O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4 H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl(2) as the oxidant afforded the 3-chloro-2-substituted-4 H-furo[3,2- c]chromen-4-one 3. 相似文献
4.
Ashraf A. Aly Esam A. Ishak Ahmed M. Shwaky Asmaa H. Mohamed 《Monatshefte für Chemie / Chemical Monthly》2020,151(2):223-229
Quinoline-2,4-diones reacted with 2-[bis(methylthio)methylene]malononitrile in DMF/Et3N to produce 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carbonitriles and 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carboxamides in state of 2-imino-substituted 4-(methylthio)-5,6-dihydro-2H-pyrano[3,2-c]quinolone-3-carbonitriles. The structures of all new products were proved using NMR, IR, and mass spectral data. The possible mechanism for the reaction is also discussed. 相似文献
5.
Kojima K Isaka K Ondognii P Zevgeegiin O Gombosurengyin P Davgiin K Mizukami H Ogihara Y 《Chemical & pharmaceutical bulletin》2000,48(3):353-356
Four novel prenyl-furocoumarin type sesquiterpenoid derivatives, 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-3-[4,8-dimethyl-3(E),7-nonadie nyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-3-[4,8-dimethyl-3(E),7-nonadie nyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-3-[4-methyl-5-(4-methyl-2-furyl)- 3(E)-pentenyl]-furo[3,2-c]coumarin, and 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-3-[4,8-dimethyl-3(E),7-nonadie nyl]-furo]3,2-c]coumarin were isolated from the roots of Ferula ferulaeoides [corrected]. Their structures were established by detailed spectral analysis and the biosynthetic pathway leading to these prenyl-furocoumarin type sesquiterpenoids is proposed based on these structures. 相似文献
6.
Choudhary MI Nur-E-Alam M Akhtar F Ahmad S Baig I Ondögnii P Gombosurengyin P Atta-ur-Rahman 《Chemical & pharmaceutical bulletin》2001,49(10):1295-1298
Five new peltogynoids, irisoids A-E (1-5), have been isolated from the underground parts of Iris bungei. The structures of the new compounds were established on the basis of spectroscopic methods and were found to be 1,8,10-trihydroxy-9-methoxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (1), 1,8-dihydroxy-9,10-dimethoxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (2), 1,10-dihydroxy-8,9-dimethoxy-[1]benzopyrano-13,2-c][2]-benzopyran-7(5H)-one (3), 1,8-dihydroxy-9,10-methylenedioxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (4), and 1,8,11-trihydroxy-9,10-methylenedioxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (5). The structure of irisoid B (2) was established unambiguously by X-ray diffraction study. 相似文献
7.
3-Bromo- or 3-iodo-cinnoline (and 4-substituted analogues) are condensed with terminal alkynes in the presence of Pd and Cu compounds as catalysts to give the 3-alkynyl-derivatives. When 4-chloro- or 4-phenoxy-compounds are used, the products react with amines, in the presence of copper(I) iodide, to form pyrrolo[3,2-c]cinnolines and with hydrazines to give either the same ring system or a pyrazolo[4,3-c]cinnoline. Hydrolysis of 3-alkynyl-4-phenoxycinnoline to 3-alkynyl-4(1H)-cinnoline, followed by cyclisation, yields the furo[3,2-c]cinnoline. Attempts to condense 3-halogenocinnolines with alkenes gave variable results: 3-phenyl ethenyl- and 3(2-pyridylethenyl)-4-(1H)-cinnolinones were obtained but 3-bromocinnoline gave the 3,3′-bicinnolinyl. Action of palladium acetate in the presence of ethyl acrylate converted 3-bromo-4-phenoxycinnoline into benzofuro[3,2-c]cinnoline and 3-bromo-4-phenylaminocinnoline into indolo[3,2-c]cinnoline. 相似文献
8.
Syntheses of [3,2-c]-,[3,2-b]-,and [2,3-c]-2,2-dimethyl-2H-pyranopyridines via Claisen rearrangement of propargyl ethers are described. An alternative approach to the [2,3-b]-isomer is reported. 相似文献
9.
Imino Diels-Alder reaction of imines with 2,3-dihydrofuran or 3,4-dihydro-2H-pyran proceeded smoothly in the presence of a catalytic amount (0.5 mol %) of ytterbium triflate to afford furo[3,2-c]- and pyrano[3,2-c] quinolines conveniently in high yield. 相似文献
10.
《Journal of Saudi Chemical Society》2014,18(5):513-519
One pot synthesis and characterization of new 5-[2′-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-4,5,6,7-tetrahydro-thieno[3,2-c]pyridines (3a–k) using amides (2a–k) were reported. The prepared 5-[2′-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (3a) is a bioisostere of 4′-(6,7-dihydro-4H-thieno [3,2-c]pyridin-5-ylmethyl)-biphenyl-2-carboxylic acid (1), having good in vivo antithrombotic activity compared with Clopidogrel. The new tetrazole derivatives (3a–k) were screened for their in vitro activity as platelet aggregation inhibitors. 相似文献
11.
It was previously reported that methyl oleanonate (5) and lanost-8-en-3-one (10) give predominantly [3,2-c]isoxazoles. On the contrary, we have confirmed that both compounds 5 and 10 do not give [3,2-c]isoxazoles but rather afford regioselectively [2,3-d]isoxazoles in good yields. Consequently, a new lanostane triterpenoid with a cyano-enone functionality in ring A was synthesized in two steps from the corresponding [2,3-d]isoxazole, which is interesting from the perspective of biological activity because lanosterol is the biogenetic precursor of steroids. 相似文献
12.
4-Chloro-8-methoxy-11H-indolo[3,2-c]quinoline could be obtained from 8-chloro-2,3-dihydro-1H-quinolin-4-one and 4-methoxyphenylhydrazine by applying Fischer's indole synthesis. Its nitration led to the 7-nitro derivative which was reduced to 7-amino-4-chloro-8-methoxy-11H-indolo[3,2-c]quinoline when Raney nickel was employed as a catalyst and to 7-amino-8-methoxy-11H-indolo[3,2-c]quinoline when palladium charcoal was used. Oxidation of the amines by potassium nitrosodisulfonate produced the corresponding 11H-indolo[3,2-c]quinoline-7,10-diones. Displacement of the methoxy group by (N,N-diethylamino)ethylamine or by N-methylpiperazine afforded the 8-aminoquinones. The quinones unsubstituted at the 4-position were more cytotoxic than the previously described 2-methoxy-11H-indolo[3,2-c]quinoline-1,4-diones. 相似文献
13.
Chemistry of Natural Compounds - 1. The synthesis of 17β-hydroxyandrostano[3,2-c]pyrazole and of cholestano[3,2-c]pyrazole has been effected by the reaction of the corresponding... 相似文献
14.
Substituted 2-dichloromethyl-4-methyl-2,3-dihydrofuro[3,2-c]quinolines were obtained by cyclization of substituted 2-methyl-3-(3,3-dichloroallyl)-4-hydroxquinolines, and 2-dichloromethyl-2,4-dimethyl-2,3-dihydrofuro[3,2-c]quinolines were isolated from 2-methyl-3-(2-methyl-3,3,dichloroallyl)-4-hydroxyquinolines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 84–86, January, 1973. 相似文献
15.
Synthesis and nitration of NH- and N-vinyl-4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines
T. N. Borisova I. A. Stazharova A. É. Aliev N. S. Prostakov A. V. Varlamov 《Chemistry of Heterocyclic Compounds》1991,27(10):1105-1109
It has been shown that the most efficient catalysts for the synthesis of 4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridine from 1,2,5-trimethylpyridin-4-one and acetylene under Trofimov conditions are rubidium and potassium hydroxides. Use of Triton B or a mixture of trimethylbenzylammonium chloride with rubidium hydroxide as catalyst gives O-alkylated oxime. Their configurations and conformations were established through separation of the individual isomers of 1-vinyl-4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines. Acetyl nitrate nitration of the cis isomer of this compound gave the 2- and 3-nitro derivatives. Similar nitration of 4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridine gave the 2-nitro-7-hydroxy derivative.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1375–1380, October, 1991. 相似文献
16.
R. S. Alekseyev A. V. Kurkin M. A. Yurovskaya 《Chemistry of Heterocyclic Compounds》2011,47(5):584-596
The possibility of preparing 1,2,3,4,6,7,8,9-octahydro-5H-pyrrolo[3,2-c:4,5-c']dipyridines using the Piloty-Robinson reaction
has been studied under various conditions. A novel method is proposed for the synthesis of the aromatic 3,6-diazacarbazole
(5H-pyrrolo[3,2-c:4,5-c']dipyridine) from 2,8-dibenzoyl-1,2,3,4,6,7,8,9-octahydro-5H-pyrrolo[3,2-c:4,5-c']dipyridine obtained
for the first time by the Piloty- Robinson method under thermal conditions. 相似文献
17.
In this paper, a straightforward and valid three-component Michael/cyclization reaction of (E)-1-methyl-3-(arylidene)piperidin-4-ones, 2-(sulfonyl)acetonitriles, and aromatic aldehydes was explored for the preparation of potentially biologically active 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridines under mild reaction conditions. More diverse 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine derivatives were constructed in satisfactory yields (up to 97%). The chemical structure of newly synthesized 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridines were identified with 1H-NMR, 13C-NMR, and mass spectrometry analysis. The recommendable method features a simple and direct workup, easy access to initial materials, high atom utilization efficiency, high final product yields, and a wide range of substrate adaptability. 相似文献
18.
Jagtap PG Baloglu E Southan G Williams W Roy A Nivorozhkin A Landrau N Desisto K Salzman AL Szabó C 《Organic letters》2005,7(9):1753-1756
[reaction: see text] The synthesis of 6,11-dihydro-5H-indeno[1,2-c]isoquinolin-5-ones from the base-promoted condensation reaction of homophthalic anhydride and 2-(bromomethyl)-benzonitrile and a convenient method for the synthesis of indolo[3,2-c]isoquinolinones are described. 相似文献
19.
A. A. Aly 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):3079-3096
Possible approaches to the synthesis of functionalized, pyrimido[5′,4′:4,5]thieno [3,2-c]pyridazines 2-18 , pyridazino[3′,4′:4,5]thieno[2,3-d]triazines 19, 20a,b and pyrido[3′,2′:4,5]thieno[3,2-c]pyridazines 22a,b are described. The sequence involves the heterocyclization of 6-amino-1,3-diphenyl-1,4-dihydrothieno[3,2-c]pyridazine-7-carboxamide (1) with appropriate reagents. The antimicrobial activity of some the newly synthesized compounds was examined. All tested compounds proved to be active as antibacterial and antifungal agents. 相似文献
20.
P Helissey S Giorgi-Renault J Renault S Cros 《Chemical & pharmaceutical bulletin》1989,37(9):2413-2416
With the aim of obtaining new antitumor drugs more active than previously described 11H-indolo[3,2-c]quinoline-1,4-diones and 7,8,9,10-tetrahydro-11H-indolo[3,2-c]quinoline-1,4-diones, the synthesis and activities of a series of 3-substituted 11H-pyrido[3',4':4,5]pyrrolo[3,2-c]quinoline-1,4-diones and of 7,8,9,10-tetrahydro-11H-pyrido-[3',4':4,5]pyrrolo[3,2-c] quinoline-1,4-diones were studied. Some quinones were more cytotoxic in vitro towards L1210 leukemia cells but were not active in vivo towards murine P388 leukemia. 相似文献