- Synthesis and antitubercular activity of 1- and 3-substituted benzo[: G] isoquinoline-5,10-diones
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In this study, a small library of twenty benzo[g]isoquinoline-5,10-diones were synthesized in a novel straightforward approach, starting from 2-methyl-1,4-naphthoquinone (vitamin K). An intramolecular Heck reaction of a N-vinylacetamide was a crucial step in the synthetic route, at which the combination of cesium carbonate and a bulky, electron rich trialkylphosphine (tBuCy2P.HBF4) provided high 6-endo-trig selectivity. The anti-tubercular activity against Mycobacterium tuberculosis H37Ra and acute cytotoxicity against J774 A.1 macrophages were studied. From the structure activity relationship, it could be derived that in general the substitution of position 3 yielded analogs with a higher antitubercular potency. Among these, two analogs, 27a and 27b, showed remarkable activity with minimal inhibition concentrations of respectively 28.92 μM and 1.05 μM, and acute cytotoxic concentrations of >128 μM and 34.85 μM. In addition, the analogs and their possible metabolites were evaluated using a Vitotox assay to study the possibility of genotoxicity. Results indicated that none of the evaluated analogs and their possible metabolites showed early signs of genotoxicity.
- Smets, Robert J.,Torfs, Eveline,Lemière, Filip,Cos, Paul,Cappoen, Davie,Abbaspour Tehrani, Kourosch
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- Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds
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Antimicrobial activities of two azafluorenones, four 1-azaanthraquinones, five 2-azaanthraquinones, and one 2-azaquinone were tested. Several azaanthraquinones possessed broad, potent activity, while the azafluorenones demonstrated weak activity. The following structure-activity relationship was postulated: (1) activity decreased in the order 2-azaanthraquinones > 1-azaanthraquinones > azafluorenones; and (2) a hydroxyl group at the peri-carbonyl group enhanced activity. In addition, correlations among reduction potential, hydrophobic parameter, and antimicrobial activity were discussed.
- Koyama, Junko,Morita, Izumi,Kobayashi, Norihiro,Osakai, Toshiyuki,Usuki, Yoshinosuke,Taniguchi, Makoto
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- Isoquinoline compound and its preparation method, the organic electroluminescent device
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The invention provides isoquinoline compounds and a preparation method thereof, and an organic light emitting diode. The isoquinoline compounds are as shown in a molecular formula (I) in the specification. Compared with the prior art, the isoquinoline compounds provided by the invention are prepared by introducing Q1, Q2, Ar1, Ar2, Ar3 and Ar4 groups into benzo[g]isoquinoline compounds, so electronic density and skills can be improved; meanwhile, R1 can improve performances of the isoquinoline compounds, so the organic light emitting diode containing the isoquinoline compounds as shown in the molecular formula (I) has the characteristics of high brightness, good heat resistance, long service life, high efficiency, etc.
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Paragraph 0135-0138
(2018/03/24)
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- Synthesis of N-substituted 1,2-dihydrobenz[g]isoquinoline-5,10-diones
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The synthesis of N-substituted 1,2-dihydrobenz[g]isoquinoline-5,10-diones was envisaged as part of?our?research on structural modifications of pentalongin, the active principle of Pentas longiflora Oliv.?Therefore, a synthesis of the 2-aza analogues of this natural pyranonaphthoquinone with an acid-mediated intramolecular cyclization of different N-protected 2-(((2,2-dimethoxyethyl)amino)methyl)-1,4-naphthoquinones in the key step was conducted. The synthesized 1,2-dihydrobenz[g]isoquinoline-5,10-diones represent a new class of compounds, which has been undescribed in organic chemistry.
- Jacobs, Jan,Kesteleyn, Bart,De Kimpe, Norbert
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p. 4985 - 4992
(2008/09/21)
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- Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones
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2-(3- and 2-Pyridylcarbonyl)benzoic acids (2,3), 2-(2-pyridylcarbonyl) thiophene-3-carboxylic acid (6), 2-(3-quinolylcarbonyl)benzoic acid (10), and most of the corresponding esters (compounds 1, 7 and 9) are readily synthesized and involved in a deprotonation-condensation sequence. Biologically active aza-anthraquinones such as benzo[g]isoquinoline-5,10-dione (2-azaanthraquinone, 4) and benzo[g]quinoline- 5,10-dione (1-azaanthraquinone, 5) are prepared using the strategy. Extension to other heterocyclic quinones such as thieno[3,2-g]quinoline-4,9-dione (8) and benzo[j]phenanthridine-7,12-dione (11) is also investigated.
- Rebstock, Anne-Sophie,Mongin, Florence,Trecourt, Francois,Queguiner, Guy
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p. 291 - 295
(2007/10/03)
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- Effect of Boron Trifluoride-Diethyl Ether (BF3*OEt2) in the Diels-Alder Reaction of Quinoline- and Isoquinoline-5,8-dione with Unsymmetrical Aliphatic Dienes: Theroretical Study on the Orientation of Cycloadditions
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The Diels-Alder reaction of quinoline- and isoquinoline-5,8-dione with piperylene gave regioisomers of the substituted azaanthraquinones, while the Lewis acid catalyst boron trifluoride-diethyl ether showed a drastic effect on regioseletivity in the reactions with piperylene.The Frontier Molecular Orbital (FMO) theory (caculated by CNDO/2 method) was applied to explain the orientation of the catalysed regioselective cycloadditions, by considering secondary orbital interactions.
- Ohgaki, Eriko,Motoyoshiya, Jiro,Narita, Susumu,Kakurai, Toshio,Hayashi, Sadao,Hirakawa, Kiyo-ichi
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p. 3109 - 3112
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF AZAANTHRAQUINONES VIA POLAR ADDITION TO HETARYNE INTERMEDIATES. USE OF CARBANIONS DERIVED FROM 32-CYANO-1(3H)-ISOBENZOFURANONES
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A convenient synthesis of 2-azaanthraquinones using the reaction of carbanions derived from 3-cyano-1(3H)-isobenzofuranones which serve as 1,4-dipole equivalents and hetaryne intermediates generated from bromopyridines and lithium diisopropylamide is reported.
- Khanapure, Subhash P.,Biehl, Edward R.
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p. 2643 - 2650
(2007/10/02)
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- Cycloaddition Routes to Azaanthraquinone Derivatives. 1. Use of Azadienophiles
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The mono- and diazanaphthoquinones underwent facile cycloaddition with cyclic and alicyclic dienes, and in the majority of these cycloadditions the initial 1:1-cycloadducts or their tautomers and intermediate products formed in the oxidation procedure leading to the final azaanthraquinones were isolated.Quinoline-5,8-dione and 1-methoxy-1,3-cyclohexadiene gave the 8-methoxy isomer in an essentially regiospecific cycloaddition; isoquinoline-5,8-dione, however, gave both the 5- and 8-methoxy isomers in a 2.8:1 ratio.These structural assignments were verified by alternative syntheses of the possible isomers using heteroatom-directed lithiation procedures.
- Potts, Kevin T.,Bhattacharjee, Debkumar,Walsh, Eileen B.
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p. 2011 - 2021
(2007/10/02)
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- SYNTHESIS OF 2-AZAANTRAQUINONE AND ITS DERIVATIVES
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The acylation of benzene, toluene, and chlorobenzene with cinchomeronic acid anhydride in the presence of AlCl3, has given in each case both possible isomers of the corresponding aroylpyridine carboxylic acid.It was found that the yields of reaction products and their isomeric compositions depend on the conditions of performing the reaction.The intramolecular cyclization on the isomeric keto acids in the presence of 2percent oleum has given 2-azaanthraquinone and chlorine derivatives of it.
- Artamonov, A. A.,Shneider, T.,Baranova, N. V.
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p. 397 - 401
(2007/10/02)
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