- AROYLQUINOLINE COMPOUNDS
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A serious of nitro heterocyclic derivatives including a structure of formula (I) are provided. In formula (I), P, Q and R1 to R8 are defined in the specification. The derivatives disclosed in the present invention are characterized in inhibiting tubulin p
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Page/Page column 14
(2011/11/13)
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- 5-Amino-2-aroylquinolines as highly potent tubulin polymerization inhibitors. Part 2. The impact of bridging groups at position C-2
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A variety of studies on the modification of combretastatin A-4 triggered our interest in the impact of the linkers between the 3,4,5-trimethoxyphenyl ring and 5-amino-6-methoxyquinoline on biological activity. The replacement of the carbonyl group with bo
- Lee, Hsueh-Yun,Chang, Jang-Yang,Nien, Chih-Ying,Kuo, Ching-Chuan,Shih, Kuang-Hsing,Wu, Chun-Hsein,Chang, Chi-Yen,Lai, Wen-Yang,Liou, Jing-Ping
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experimental part
p. 8517 - 8525
(2012/02/03)
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- Mono-nitration of aromatic compounds via nitrate salts
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A method of nitrating a compound selected from the group consisting of is provided.
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Page/Page column 6; 10
(2008/06/13)
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- Mono-nitration of aromatic compounds via their nitric acid salts
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Aromatic compounds bearing a basic nitrogen atom can be converted to the corresponding nitric acid salts. Mono-nitration of the compounds can be carried out by adding a dichloromethane solution of the salts to sulfuric acid, or by adding acetyl chloride (or trifluoroacetic anhydride) to a dichloromethane solution of the salts. This protocol provides, among other benefits, the most convenient and reliable way for the prevention of over-/under-nitration and is especially suitable for scale-up.
- Zhang, Pingsheng,Cedilote, Miall,Cleary, Thomas P.,Pierce, Michael E.
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p. 8659 - 8664
(2008/03/30)
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- Novel quinolinequinone antitumor agents: Structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1)
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A series of quinolinequinones bearing various substituents has been synthesized, and the effects of substituents on the metabolism of the quinones by recombinant human NAD(P)H:quinone oxidoreductase (hNQO1) was studied. A range of quinolinequinones were selected for study, and were specifically designed to probe the effects of aryl substituents at C-2. A range of 28 quinolinequinones 2-29 was prepared using three general strategies: the palladium(0) catalyzed coupling of 2-chloroquinolines, the classical Friedlaender synthesis and the double-Vilsmeier reaction of acetanilides. One example of an isoquinolinequinone 30 was also prepared, and the reduction potentials of the quinones were measured by cyclic voltammetry. For simple substituents R2 at the quinoline 2-position, the rates of quinone metabolism by hNQO1 decrease for R2=Cl>H～Me>Ph. For aromatic substituents, the rate of reduction decreases dramatically for R 2=Ph>1-naphthyl>2-naphthyl>4-biphenyl. Compounds containing a pyridine substituent are the best substrates, and the rates decrease as R 2=4-pyridyl>3-pyridyl>2-pyridyl>4-methyl-2-pyridyl>5- methyl-2-pyridyl. The toxicity toward human colon carcinoma cells with either no detectable activity (H596 or BE-WT) or high NQO1 activity (H460 or BE-NQ) was also studied in representative quinones. Quinones that are good substrates for hNQO1 are more toxic to the NQO1 containing or expressing cell lines (H460 and BE-NQ) than the NQO1 deficient cell lines (H596 and BE-WT).
- Fryatt, Tara,Pettersson, Hanna I.,Gardipee, Walter T.,Bray, Kurtis C.,Green, Stephen J.,Slawin, Alexandra M. Z.,Beall, Howard D.,Moody, Christopher J.
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p. 1667 - 1687
(2007/10/03)
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- Direct methoxylation of nitroarenes and nitroazaarenes with alkaline methoxides via nucleophilic displacement of an aromatic hydrogen atom
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Treatment of 1,3-dinitrobenzene and 5-substituted derivatives with excess potassium or sodium methoxide in 1,3-dimethylimidazolidin-2-one (DMI) at room temperature results in the displacement of an aromatic hydrogen at the 4-position by methoxide, affording 2,4-dinitroanisole and its 6-substituted derivatives, respectively, in low to moderate yield. In contrast, an equimolar reaction under similar conditions leads to the replacement of the nitro group in preference to the ring hydrogen. The reaction does not take place with lithium methoxide as a base. Mono- and dinitronaphthalenes and nitroquinolines undergo similar displacement of a hydrogen atom at the position ortho or para to the nitro group, giving the corresponding methoxy derivatives in moderate yield. A slow addition of the nitro compound to a large excess of potassium methoxide under an oxygen atmosphere has been found to enhance the conversion and improve the product yield. On the basis of the product distribution as well as the kinetic isotope effect kH/kD = 2.1, direct displacement of a ring hydrogen atom by methoxide ion has been interpreted in terms of the rate-determining release of an ipso-hydrogen atom as a proton from the initially formed Meisenheimer adduct.
- Kawakami, Takehiko,Suzuki, Hitomi
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p. 1259 - 1264
(2007/10/03)
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- Novel quinolinequinone antitumor agents: Structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1)
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The effects of functional group changes on the metabolism of novel quinolinequinones by recombinant human NAD(P)H:quinone oxidoreductase (NQO1) are described. Overall, the quinolinequinones were much better substrates for NQO1 than analogous indolequinones, with compounds containing heterocyclic substituents at C-2 being among the best substrates.
- Fryatt, Tara,Goroski, Dean T.,Nilson, Zachary D.,Moody, Christopher J.,Beall, Howard D.
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p. 2195 - 2198
(2007/10/03)
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- Synthetic Routes to the Carcinogen IQ and Related 3H-Imidazoquinolines
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2-Amino-3-methyl-3H-imidazoquinoline (IQ, 1a) and four new IQ homologues, viz. its 7-methyl, 8-methyl, 9-methyl and 7,9-dimethyl derivatives 1c-1f, have been conveniently synthesized from the appropriate 6-methoxyquinolines 3 rather than from the p
- Ronne, Erik,Grivas, Spiros,Olsson, Kjell
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p. 823 - 830
(2007/10/02)
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- Aromatic Ring Cleavage in 6-Methoxyquinolines and 2-Methoxynaphthalene with Fuming Nitric Acid
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Two 6-methoxyquinolines and 2-methoxynaphthalene, on prolonged treatment with fuming nitric acid, give major products resulting from benzene ring cleavage but retaining all carbons of the cleaved ring.Methoxyisoquinolines were not cleaved under the same conditions.
- Balczewski, Piotr,Morris, Gareth A.,Joule, John A.
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p. 2514 - 2523
(2007/10/02)
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