- SYNTHETIC MYCOTOXIN ADSORBENTS AND METHODS OF MAKING AND UTILIZING THE SAME
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The present invention relates generally to molecularly imprinted polymers (MIPs). In particular, the present invention relates to reusable, ecologically friendly MIPs that can be produced in relatively large quantities, methods of producing the same, and
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Page/Page column 0183-0187
(2022/01/03)
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- A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines
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A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments.
- Ohtsuka, Naoya,Okuno, Moriaki,Hoshino, Yujiro,Honda, Kiyoshi
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p. 9046 - 9054
(2016/10/05)
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- One-pot synthesis of primary amines from carboxylic acids through rearrangement of in situ generated hydroxamic acid derivatives
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A one-pot synthesis of primary amines from carboxylic acids through a Lossen rearrangement of hydroxamic acid derivatives, which were in situ generated by the reaction of carboxylic acids with O-trimethylsilylhydroxylamine (NH2OTMS) and carbonyl diimidazole (CDI, 1.5 equiv) in dimethyl sulfoxide at room temperature, has been achieved. This one-pot method could be applied to various carboxylic acids such as aromatic, heteroaromatic, aliphatic, and optically active substrates.
- Hoshino, Yujiro,Ohtsuka, Naoya,Okada, Takuya,Honda, Kiyoshi
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supporting information
p. 5304 - 5307
(2016/11/16)
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- Self-propagated Lossen rearrangement induced by a catalytic amount of activating agents under mild conditions
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A mild self-propagated Lossen rearrangement induced by a catalytic amount of activating agents in medium to high polar organic solvents has been developed. The rearrangement of aromatic and aliphatic hydroxamic acids in the presence of a catalytic amount (0.01 equiv) of acetic anhydride and an equimolar amount of base such as well-dried potassium carbonate afforded the corresponding amines in high yields. This alternative to traditional Lossen rearrangement provides a simple and mild method for the synthesis of amines from free hydroxamic acids.
- Hoshino, Yujiro,Shimbo, Yuki,Ohtsuka, Naoya,Honda, Kiyoshi
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supporting information
p. 710 - 712
(2015/01/30)
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- 6-Methoxy-7-benzofuranoxy and 6-methoxy-7-indolyloxy analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a potent and selective α1D-adrenoceptor antagonist
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Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, α1-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclohexane, or especially by ortho,meta-fused benzene preferentially elicits α1D-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho heterodisubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest α1D-AR antagonist affinity (pA2 9.58) with significant α1D/ α1A and α1D/α1B selectivity. In addition, compared both to α1D-AR antagonists structurally related to 1 and to the well-known α1D-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral α1-AR antagonist behavior.
- Fumagalli, Laura,Pallavicini, Marco,Budriesi, Roberta,Bolchi, Cristiano,Canovi, Mara,Chiarini, Alberto,Chiodini, Giuseppe,Gobbi, Marco,Laurino, Paola,Micucci, Matteo,Straniero, Valentina,Valoti, Ermanno
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p. 6402 - 6412
(2013/09/23)
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- Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities
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An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.
- Maiti, Arup,Reddy, P. V. Narasimha,Sturdy, Megan,Marler, Laura,Pegan, Scott D.,Mesecar, Andrew D.,Pezzuto, John M.,Cushman, Mark
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experimental part
p. 1873 - 1884
(2009/12/31)
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- Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO-NHOH) to anilines
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Without using activating agents, a variety of free aromatic hydroxamic acids could be rearranged to aromatic amines in the presence of base alone. The Royal Society of Chemistry 2009.
- Hoshino, Yujiro,Okuno, Moriaki,Kawamura, Eri,Honda, Kiyoshi,Inoue, Seiichi
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supporting information; experimental part
p. 2281 - 2283
(2009/09/06)
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- Synthesis of the pentacyclic core of lihouidine
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The pentacyclic base of the sponge-derived alkaloid lihouidine has been assembled from two quinoline fragments. The key step is a nitration-promoted cyclization to form the C-C bond between the two quinoline units.
- Feldman, Ken S.,Coca, Adiel
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p. 2136 - 2138
(2008/09/19)
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- Development of 3,4-dihydro-2H-benzo[1,4]oxazine derivatives as dual thromboxane A2 receptor antagonists and prostacyclin receptor agonists
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We discovered a novel series of 3,4-dihydro-2H-benzo[1,4]oxazin-8- yloxyacetic acid derivatives as potent dual-acting agents to block the TXA 2 receptor and to activate the PGI2 receptor. We report the synthesis, structure-activity r
- Ohno, Michihiro,Tanaka, Yoichiro,Miyamoto, Mitsuko,Takeda, Takahiro,Hoshi, Kazuhiro,Yamada, Naohiro,Ohtake, Atsushi
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p. 2005 - 2021
(2007/10/03)
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- On the synthesis of two dimethoxy-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline regioisomers
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Many marine alkaloids are biologically active products and possess the 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline core as a common feature. This is a report of the synthesis of two of the title molecules with confirmation of their structure.
- Chackal, Sarah,Dudouit, Fabienne,Houssin, Raymond,Henichart, Jean-Pierre
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p. 615 - 622
(2007/10/03)
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- Acetamidoquinone and acetamidohydroxy derivatives as inhibitors for both dihydroxyacetamido epoxidase and dehydrogenase
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A series of monohydroxy and dihydroxyacetanilides, acetamidoquinones and bromoacetamidoquinones have been synthesised and tested as substrates and/or inhibitors of highly purified dihydroxyacetamido epoxidase (DHAE) and dihydroxy acetamido dehydrogenase (DHADH) from Streptomyces LL-C10337. None was found to act as substrates but many selectively inhibit the enzymes. Kinetic analysis has shown that all the compounds act as reversible competitive inhibitors with respect to the substrates 2,5-dihydroxyacetanilide and 2,3-epoxy-1,4-benzoquinone-5-acetanilide. Monohydroxy acetanilides showed weak inhibition to these enzymes compared to the dihydroxy derivatives while the more powerful inhibitors were the benzoquinoneacetanilide and its 5-bromo equivalent.
- Whiteley, Chris G.
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p. 1221 - 1227
(2007/10/03)
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- An efficient synthesis of the new benzo[c]pyrido[2,3,4-kl]acridine skeleton
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A series of molecules of therapeutic interest, possessing the new skeleton of 1H-benzo[c]pyrido[2,3,4-kl]-acridine with acyl or aminoacyl and methoxy or aminoalkoxy substituents on the aromatic homocycles were synthesized by means of a Friedlaender-type r
- Chackal, Sarah,Houssin, Raymond,Henichart, Jean-Pierre
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p. 3502 - 3505
(2007/10/03)
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- Synthetic studies of the pyrroloquinoline nucleus of the makaluvamine alkaloids. Synthesis of the topoisomerase II inhibitor makaluvamine D
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A new synthesis of the pyrrolo[4,3,2-de]quinoline system characteristic of a class of marine alkaloids which includes the prianosins, discorhabdins, and other antineoplastic agents has been developed. The approach is exemplified in a total synthesis of ma
- White, James D.,Yager, Kraig M.,Yakura, Takayuki
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p. 1831 - 1838
(2007/10/02)
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- Nucleophilic photosubstitutions of o-methoxynitrobenzenes
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We report a new synthesis of 3-nitroveratrole, based on the directed lithiation of veratrole, and photochemical substitutions of both 3-nitroveratrole and o-nitroanisole with several nucleophiles.Both aromatic substrates undergo photocyanation meta to the nitro group.With hydroxide ion, 3-nitroveratrole reacts meta to the nitro group, but 2-nitroanisole undergoes replacement of either substituent, the proportion of reaction at each site depending upon the OH(-) concentration. 3-Nitroveratrole undergoes an inefficient reaction with butylamine at each methoxy group; this reaction is apparently second order in amine.The reaction between o-nitroanisole and diethylamine results only in photohydrolysis.Keywords: photosubstitution, nucleophilic, 3-nitroveratrole, o-nitroanisole
- Bunce, Nigel J.,Stephenson, Karen Labonte
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p. 220 - 226
(2007/10/02)
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- Triazinyl reactive dyes containing additional fiber reactive groups bound through the sulfonylalkylaminoalkylamino bridge
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The invention relates to novel useful reactive dyes of the formula I STR1 in which: F is a radical selected from the group consisting of metal-free or metal-containing monoazo or disazo dyes containing at least one --SO3 H group, anthraquinone dyes, sulfophthalocyanine dyes, formazan dyes, phenazine dyes, oxanine dyes and nitroaryl dyes, R is hydrogen, C1 -C4 alkyl which is unsubstituted or substituted with --COOH or --SO3 H, cyanoethyl, or hydroxyethyl, X is fluorine, chlorine, bromine, --SO3 H, phenylsulfonyl or C1 -C4 -alkylsulfonyl, P is 1 or 2 and A is a radical of the formula STR2 in which: the groups designated "alk" are independently of each other straight or branched polymethylene radicals having 2 to 6 carbon atoms, and Z is β-halogenoethyl, vinyl, β-sulfatoethyl, β-thiosulfatoethyl or βacetoxyethyl.
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- A SYNTHESIS OF AAPTAMINE
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A five-step synthesis of the unusual marine alkaloid aaptamine (1) from veratrole is described (Scheme 1).
- Kelly, T. Ross,Maguire, Martin P.
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p. 3033 - 3036
(2007/10/02)
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- Polar Effects in Free Radical Reactions. Homolytic Aromatic Amination by the Amino Radical Cation, +NH3: Reactivity and Selectivity
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Small amounts of Fe(II) salt initiate redox chains with hydroxyamino-O-sulfonic acid (HSA) and aromatic compounds leading to the amination of the aromatic ring.The positional and substrate selectivity with a variety of substituted benzenes show the important role of the electrophilic character of the radical +NH3.Hammett relationships with ? and ?+ are roughly observed.The lower sensitivity to polar effects of the radical +NH3 compared with (CH3)2+NH is explained by the different reaction enthalpies.The different positional selectivity obtained with anisole and the redox system +NH3OH/Ti(III) is discussed.
- Citterio, Attilio,Gentile, Anna,Minisci, Francesco,Navarrini, Valter,Serravalle, Marco,Ventura, Susanna
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p. 4479 - 4482
(2007/10/02)
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- A NOVEL AMINATION OF AROMATIC AND HETEROAROMATIC COMPOUNDS
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Vinyl azides act as NH2(+) equivalents in reaction with aromatic or heteroaromatic lithium derivatives thus providing a direct method for amination of such compounds.
- Hassner, Alfred,Munger, Paul,Belinka, A. Benjamin, Jr
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p. 699 - 702
(2007/10/02)
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- The melosatins-a novel class of alkaloids from melochia tomentosa1 1 Part 13 in the series, Potential Carcinogens. For Part 12 see Ref. 2.
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Details of the isolation of malosatin A, B, and C and the synthesis of melosatin A are presented. Melosatin C has been characterized as 7-methoxy-4-(5-phenylpentyl)isatin. Several Me and OMe substituted isatins are synthesized as models and UV and mass sp
- Kapadia,Shukla,Basak,Sokoloski,Fales
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p. 2441 - 2447
(2007/10/02)
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