- Asymmetric total synthesis of nigerone
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An enantioselective synthesis of the chiral bisnaphthopyrone natural product nigerone is reported. The key step was an eight-step isomerization process to form the final natural product. The isomerization precursor was constructed via asymmetric oxidative
- DiVirgilio, Evan S.,Dugan, Elizabeth C.,Mulrooney, Carol A.,Kozlowski, Marisa C.
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Read Online
- Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains
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Analyses (UV, IR, 1H-NMR, MS) of the main phenolic fraction isolated by sequential separation on normal-phase and argentation chromatography on silica gel confirmed the presence of monoenoic and dienoic homologues of 1,3-dihydroxy-5-n-alkylbenzene in acet
- Kozubek, Arkadiusz,Tyman, John H. P.
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Read Online
- FGFR4 kinase inhibitor, preparation method and uses thereof
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The present invention relates to a compound represented by a formula (I), or a pharmaceutically acceptable salt, a solvate, a polymorph or an isomer thereof, and uses in preparation of drugs for treatment of FGFR4 mediated diseases.
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Paragraph 0203-0204; 0208-0209
(2020/04/17)
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- The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols
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A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone and (±)-isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C?C bond formation.
- He, Zhen,Pulis, Alexander P.,Procter, David J.
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supporting information
p. 7813 - 7817
(2019/05/15)
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- Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)3·9H2O
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A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.
- Thurow, Samuel,Fernandes, Alessandra A. G.,Quevedo-Acosta, Yovanny,De Oliveira, Matheus F.,De Oliveira, Marcelo G.,Jurberg, Igor D.
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supporting information
p. 6909 - 6913
(2019/09/12)
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- Fibroblast growth factor receptor selective inhibitor and application thereof
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The invention relates to a fibroblast growth factor receptor selective inhibitor and application thereof. The invention provides a compound of a formula (I), a three-dimensional isomer, a tautomer or a pharmaceutically acceptable salt thereof, and an appl
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Paragraph 0155; 0156; 0157
(2017/08/02)
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- Fibroblast growth factor receptor selective inhibitor and applications thereof
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The invention discloses a fibroblast growth factor receptor selective inhibitor and applications thereof. The invention provides a compound as shown in a formula (I), and a stereoisomer, a tautomer or pharmaceutically accepted salts thereof, and applicati
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Paragraph 0162-0165
(2017/08/23)
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- Convenient syntheses of 3-aryl-3,4-dihydroisocoumarins
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A convenient method for the synthesis of naturally occurring 3,4-dihydroisocoumarins by judicious use of Friedel-Craft acylation, regioselective formylation and oxidative cyclisation reactions is described. O-methylated analogues of montroumarin and thunb
- Limaye, Rohan A.,Joseph, Augustine R.,Natu, Arun D.,Paradkar, Madhusudan V.
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p. 191 - 194
(2015/06/02)
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- Controlled-deactivation cannabinergic ligands
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We report an approach for obtaining novel cannabinoid analogues with controllable deactivation and improved druggability. Our design involves the incorporation of a metabolically labile ester group at the 2′-position on a series of (-)-Δ8-THC a
- Sharma, Rishi,Nikas, Spyros P.,Paronis, Carol A.,Wood, Jodianne T.,Halikhedkar, Aneetha,Guo, Jason Jianxin,Thakur, Ganesh A.,Kulkarni, Shashank,Benchama, Othman,Raghav, Jimit Girish,Gifford, Roger S.,J?rbe, Torbj?rn U. C.,Bergman, Jack,Makriyannis, Alexandros
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p. 10142 - 10157
(2014/01/17)
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- Biomimetic asymmetric synthesis of (R)-GTRI-02 and (3 S,4 R)-3,4-dihydroxy-3,4-dihydronaphthalen-1(2H)-ones
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The NADPH-dependent tetrahydroxynaphthalene reductase (T4HNR) from Magnaporthe grisea was used for the biomimetic synthesis of (R)-GTRI-02 by stereoselective reduction of 1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl) ethanone. This also led to t
- Husain, Syed Masood,Schaetzle, Michael A.,Roehr, Caroline,Luedeke, Steffen,Mueller, Michael
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supporting information; experimental part
p. 3600 - 3603
(2012/09/07)
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- Novel 3-azaindolyl-4-arylmaleimides exhibiting potent antiangiogenic efficacy, protein kinase inhibition, and antiproliferative activity
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Tumor growth and metastasis are highly associated with the overexpression of protein kinases (PKs) regulating cell growth, apoptosis resistance, and prolonged cell survival. This study describes novel azaindolyl-maleimides with significant inhibition of PKs, such as VEGFR, FLT-3, and GSK-3β which are related to carcinogenesis. Furthermore, these compounds exhibit high kinase selectivity and potent inhibition of angiogenesis and cell proliferation, offering versatile options in cancer treatment strategies.
- Ganser, Christopher,Lauermann, Eva,Maderer, Annett,Stauder, Torsten,Kramb, Jan-Peter,Plutizki, Stanislav,Kindler, Thomas,Moehler, Markus,Dannhardt, Gerd
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p. 9531 - 9540
(2013/01/16)
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- Sequential rhodium-, silver-, and gold-catalyzed synthesis of fused dihydrofurans
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A triple cascade process was developed for the rapid synthesis of polycyclic benzo-fused dihydrofurans. The first step is a rhodium-catalyzed cyclopropanation of α-aryldiazoketones with alkenes. This is followed by a silver-catalyzed ring expansion to dih
- Wang, Hengbin,Denton, Justin R.,Davies, Huw M. L.
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supporting information; experimental part
p. 4316 - 4319
(2011/10/05)
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- MIXTURES OF MESOIONIC PESTICIDES
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Disclosed are compositions comprising (a) at least one compound selected from compounds of Formula (1), N-oxides, and salt thereof, wherein R1 is phenyl optionally substituted with up to 5 substituents independently selected from R3,
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Page/Page column 35
(2011/02/24)
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- Palladium-catalyzed intramolecular decarboxylative allylic arylation of α-aryl-γ-methylidene-δ-valerolactones
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A palladium-catalyzed intramolecular decarboxylative cyclization of α-aryl-γ-methylidene-δ-valerolactones, followed by olefin isomerization, has been developed to give fused polycyclic aromatic compounds under mild conditions. The process described here can be regarded as a formal decarboxylative allylic arylation without using a pre-formed organometallic nucleophile. The reaction can be conducted on a gram scale and the products thus obtained are further derivatized with ease.
- Shintani, Ryo,Tsuji, Takaoki,Park, Soyoung,Hayashi, Tamio
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supporting information; experimental part
p. 1697 - 1699
(2010/07/07)
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- Synthesis of heterocycle-based analogs of resveratrol and their antitumor and vasorelaxing properties
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New resveratrol (RES) analogs were developed by replacing the aromatic 'core' of our initial naphthalene-based RES analogs with pseudo-heterocyclic (salicylaldoxime) or heterocyclic (benzofuran, quinoline, and benzothiazole) scaffolds. The resulting analo
- Bertini, Simone,Calderone, Vincenzo,Carboni, Isabella,Maffei, Roberta,Martelli, Alma,Martinelli, Adriano,Minutolo, Filippo,Rajabi, Mehdi,Testai, Lara,Tuccinardi, Tiziano,Ghidoni, Riccardo,MacChia, Marco
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experimental part
p. 6715 - 6724
(2010/10/19)
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- Discovery and biological evaluation of novel cyanoguanidine P2X7 antagonists with analgesic activity in a rat model of neuropathic pain
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We disclose the design of a novel series of cyanoguanidines that are potent (IC50 ? 10-100 nM) and selective (≥100-fold) P2X7 receptor antagonists against the other P2 receptor subtypes such as the P2Y2, P2X4, and P2X3. We also found that these P2X7 antagonists effectively reduced nociception in a rat model of neuropathic pain (Chung model). Particularly, analogue 53 proved to be effective in the Chung model, with an ED50 of 38 μmol/kg after intraperitoneal administration. In addition compound 53 exhibited antiallodynic effects following oral administration and maintained its efficacy following repeated administration in the Chung model. These results suggest an important role of P2X7 receptors in neuropathic pain and therefore a potential use of P2X7 antagonists as novel therapeutic tools for the treatment of this type of pain.
- Perez-Medrano, Arturo,Donnelly-Roberts, Diana L.,Honore, Prisca,Hsieh, Gin C.,Namovic, Marian T.,Peddi, Sridhar,Shuai, Qi,Wang, Ying,Faltynek, Connie R.,Jarvis, Michael F.,Carroll, William A.
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experimental part
p. 3366 - 3376
(2010/04/03)
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- Asymmetric total synthesis of nigerone and ent-nigerone: Enantioselective oxidative biaryl coupling of highly hindered naphthols
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An enantioselective synthesis of the chiral bisnaphthopyrone natural product nigerone and its enantiomer, ent-nigerone, has been realized. The use of constrained 2-naphthol substrates was critical to producing highly functionalized chiral 1,1′-binaphthols via asymmetric oxidative biaryl coupling with 1,5-diaza-cis-decalin copper complexes. The final natural product was formed via a key eight-step isomerization process of the coupling product, bisisonigerone, and proceeded with retention of the biaryl con iguration. The axial configurations of bisisonigerone and nigerone were definitively established by a combination of circular dichroism (CD) measurements and quantum chemical CD calculations.
- Kozlowski, Marisa C.,Dugan, Elizabeth C.,DiVirgilio, Evan S.,Maksimenka, Katja,Bringmann, Gerhard
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p. 583 - 594
(2008/02/08)
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- An efficient synthesis of bibenzylic oxygen heterocycles
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The first total syntheses of naturally occurring 6-methoxy-4-(2- phenylethyl)benzofuran (1) and 2,2-dimethyl-7-methoxy-5-(2-phenylethyl)chroman (2) and the non-natural 7-methoxy-5-(2-phenylethyl)chromen-2-one (3) are described from 3,5-dimethoxyphenylacet
- Kumbhar, Virendra B.,Joseph, Augustine R.,Natu, Arun D.,Kusurkar, Radhika S.,Paradkar, Madhusudan V.
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p. 590 - 593
(2008/09/20)
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- Synthetic Approach to Hypoxyxylerone, Novel Inhibitor of Topoisomerase I
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(Equation Presented) A potential route to the topoisomerase I inhibitor hypoxyxylerone is demonstrated by a highly convergent synthesis of the penta(O-methyl) derivative. The key step in the approach is an anionic homo-Fries rearrangement, little used to
- Piettre, Arnaud,Chevenier, Emmanuel,Massardier, Christine,Gimbert, Yves,Greene, Andrew E.
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p. 3139 - 3142
(2007/10/03)
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- Use of conjugated dienones in cyclialkylations: Total syntheses of arucadiol, 1,2-didehydromiltirone, (±)-hinokione, (±)-nimbidiol, sageone, and miltirone
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Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.
- Majetich, George,Liu, Shuang,Fang, Jing,Siesel, David,Zhang, Yong
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p. 6928 - 6951
(2007/10/03)
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- Synthesis of (S)-(-)-di-O-methyl-M5032
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Synthesis of (S)-(-)-di-O-methyl-M5032 (9) has been described by esterification of 3,5-dimethoxyphenylacetyl chloride (7) with t-butyl (S)-5-hydroxy-2(E)-hexenoate (6) followed by intramolecular acylation.
- Deshpande, V. H.,Rai, Beena
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p. 1172 - 1174
(2007/10/03)
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- The Synthesis of rac-Peniolactol and Some Related Compounds
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The structure (+/-)-3,6,8-trihydroxy-3-pentadecyl-3,4-dihydroisocoumarin 1 assigned by earlier workers to peniolactol, a metabolite of Peniophora sanguinea, has been confirmed by total synthesis of this compound and some of its derivatives. - Key Words: I
- Rama, Nasim H.,Saeed, Aamer,Bird, Clive W.
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p. 711 - 714
(2007/10/02)
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- Combretastatin Analogs via Hydration of Stilbene Derivatives
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Hydration of the double bond of some stilbene congeners of Picea abies bark by TiCl4.NaBH4 reagent is described.Five racemic 1,2-diphenylethanol derivatives (9-13), structurally related to (R)-(-)combretastatin , have been obtained and characterize
- Mannila, Erkki,Talvitie, Antti
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p. 1037 - 1040
(2007/10/02)
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- The Synthesis of 1,5,7,10-Tetraoxygenated 3-Methylphenanthrenes
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Photocyclisation of the enol acetate (19) derived from 4-(2-cyano-2-(3,5-dimethoxyphenyl)acetyl)-3,5-dimethoxytoluene (17) gave 10-acetoxy-9-cyano-1,5,7-trimethoxy-3-methylphenanthrene (20) in good yield.The acetate of the phenanthrene (20) was hydrolysed
- Finnie, Alistair A.,Hill, Robert A.
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p. 873 - 894
(2007/10/02)
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- On the Synthesis of Some Chlorinated Isocoumarins
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The dihydroisocoumarin(V) and the isochroman(XII) have been synthesised during experiments on the synthesis of some natural chlorinated isocoumarins.
- Chatterjea, J. N.,Bhakta, C.,Mukherjee, Sanat K.
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p. 888 - 890
(2007/10/02)
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- Acetogenin Synthesis. Organocopper Reagents, Anions of 1,3-Dithians and of Protected Cyanohydrins as Intermediates in Ketide Side-chain Synthesis
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The synthesis is reported of 3-s-butyl-4-methyl-3,6,8-trihydroxy-3,4-dihydroisocoumarin (1a) and 3-(1-methylprop-1-enyl)-4-methyl-3,6,8-trihydroxy-3,4-dihydroisocoumarin (1b) using organocopper reagents and anions of 1,3-dithians for compound (1a), and an
- Colombo, Lino,Gennari, Cesare,Santandrea, Marco,Narisano, Enrica,Scolastico, Carlo
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p. 136 - 140
(2007/10/02)
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- Biosynthesis of Ascochitine and Synthesis of its Biogenetic Precursors
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'Enzymic trap' experiments show that the main biosynthetic pathway to ascochitine (1) involves the direct reduction of the enzyme-bound ester into aldehyde (4).Therefore the complete pathway has now been assessed.Various synthetic approaches have been tri
- Colombo, Lino,Gennari, Cesare,Scolastico, Carlo,Aragozzini, Fabrizio,Merendi, Cosetta
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p. 2549 - 2553
(2007/10/02)
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