- New inhibitors of angiogenesis with antitumor activity in vivo
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Angiogenesis is a requirement for the sustained growth and proliferation of solid tumors, and the development of new compounds that induce a sustained inhibition of the proangiogenic signaling generated by tumor hypoxia still remains as an important unmet
- Marín-Ramos, Nagore I.,Alonso, Dulce,Ortega-Gutiérrez, Silvia,Ortega-Nogales, Francisco J.,Balabasquer, Moisés,Vázquez-Villa, Henar,Andradas, Clara,Blasco-Benito, Sandra,Pérez-Gómez, Eduardo,Canales, ángeles,Jiménez-Barbero, Jesús,Marquina, Ana,Del Prado, Jaime Moscoso,Sánchez, Cristina,Martín-Fontecha, Mar,López-Rodríguez, María L.
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- Site-Selective C?H Oxygenation via Aryl Sulfonium Salts
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Herein, we report a two-step process forming arene C?O bonds in excellent site-selectivity at a late-stage. The C?O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C?O bonds using photoredox chemistry. Electron-rich, -poor and -neutral arenes as well as complex drug-like small molecules are successfully transformed into both phenols and various ethers. The sequence differs conceptually from all previous arene oxygenation reactions in that oxygen functionality can be incorporated into complex small molecules at a late stage site-selectively, which has not been shown via aryl halides.
- Sang, Ruocheng,Korkis, Stamatis E.,Su, Wanqi,Ye, Fei,Engl, Pascal S.,Berger, Florian,Ritter, Tobias
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supporting information
p. 16161 - 16166
(2019/11/03)
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- Diversity-Oriented Synthesis of Spiroannulated Benzofuran-3-one Scaffold of Leptosphaerin C and Congeners via Aryne Insertion
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A concise synthesis of functionalized cyclohexenone-fused spirobenzofuran-3-ones under mild reaction conditions was developed. The reaction proceeds via insertion of aryne into the C-O bond followed by a regioselective intramolecular conjugate addition. The use of silyl-protected acid was crucial for the transformation. This protocol was successfully applied for the synthesis of leptosphaerin C core and its novel analogues.
- Dhokale, Ranjeet A.,Mhaske, Santosh B.
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p. 4875 - 4882
(2017/05/12)
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- Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide
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The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.
- Camelio, Andrew M.,Liang, Yong,Eliasen, Anders M.,Johnson, Trevor C.,Yuan, Changxia,Schuppe, Alex W.,Houk,Siegel, Dionicio
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p. 8084 - 8095
(2015/09/01)
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- CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF
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The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.
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Page/Page column 10
(2014/10/15)
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- Hydroxy-methoxybenzoic methyl esters: Synthesis and antifeedant activity on the pine weevil, Hylobius abietis
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The pine weevil Hylobius abietis (L.) (Coleoptera: Curculionidae) feeds on the bark of coniferous seedlings and is the economically most important forestry restocking pest in large parts of Europe. Substances with an antifeedant effect may offer an environmentally friendly alternative to insecticides for the protection of planted seedlings. Bioassays were performed on commercial and synthetic methyl hydroxy-methoxybenzoates in order to determine their possible antifeedant activity. Two methyl hydroxy-methoxybenzoates were synthesized by esterification and mono-O-methylation of two dihydroxybenzoic acids. A regioselective protection-deprotection strategy was used in the synthetic pathway of the other non-commercial esters, esterification and selective pivaloylation of the less-hindered hydroxyl group of other commercial dihydroxybenzoic acids gave diester intermediates, which then were O-methylated before methanolysis of the pivaloyl group which yielded the desired non-commercial methyl hydroxy-methoxybenzoates. The five synthesized methyl hydroxy-methoxybenzoic esters were complemented with commercial samples of the five other isomers of methyl hydroxy-methoxybenzoate and spectrometric data were collected for the complete set of isomers. All ten isomers were tested for their antifeedant effect on the pine weevil. The effect varied considerably among the hydroxy-methoxybenzoic esters. Methyl 2-hydroxy-3-methoxybenzoate showed the highest effect and may thus be a candidate for practical use in pine weevil pest management.
- Legrand, Sacha,Nordlander, G?ran,Nordenhem, Henrik,Borg-Karlson, Anna-Karin,Unelius, C. Rikard
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p. 829 - 835
(2007/10/03)
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- An efficient one-pot synthesis of phenol derivatives by ring opening and rearrangement of diels-alder cycloadducts of substituted furans using heterogeneous catalysis and microwave irradiation
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The use of silica-supported Lewis acids as catalysts under microwave irradiation promotes regiospecific opening of the 7-oxa bridge of Diels-Alder cycloadducts of furan derivatives and produces polysubstituted phenols in a single step. This rapid and effi
- Moreno, Andrés,Gómez, María Victoria,Vázquez, Ester,De La Hoz, Antonio,Díaz-Ortiz, Angel,Prieto, Pilar,Mayoral, José Antonio,Pires, Elisabet
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p. 1259 - 1263
(2007/10/03)
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- SUBSTITUTED 4-(1H-BENZIMIDAZOL-2-YL)[1,4]DIAZEPANES USEFUL FOR THE TREATMENT ALLERGIC DISEASES
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The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4] diazepane derivatives of formula (1): and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.
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- Novel substituted 4-(1H-benzimidazol-2-yl) [1,4]diazepanes useful for the treatment of allergic diseases
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The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4]diazepane derivatives of formula and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.
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- Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease
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The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4]diazepane derivatives of formula (1): and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.
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- Total synthesis and absolute configuration of riccardiphenols A and B, isolated from the Liverwort Riccardia crassa
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The title compounds were synthesized as optically active forms using chiral Michael addition of the imine, prepared from 2-methylcyclohexanone and (S)-(-)-phenylethylamine, to methyl propiolate. The etherification of the intermediate triol was accomplished by TsOH-catalyzed cyclization. The absolute configurations of the natural products, riccardiphenols A and B, were established as 1 and 2, respectively.
- Tori,Hamaguchi,Sagawa,Sono,Asakawa
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p. 5362 - 5370
(2007/10/03)
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- An Investigation into the Regioselectivity of the Acid Catalysed Claisen Rearrangement of Methyl 4- and 5-Allyloxy-2-hydroxybenzoate and Derivatives
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The observed products from the acid catalysed Claisen rearrangement of the methyl esters (1c-g) indicate that, unlike the thermal reaction, regiochemical control is independent of internal hydrogen bonding.
- Harwood, Laurence M.
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p. 530 - 532
(2007/10/02)
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- Syntheses of Peptide Alkaloids, VII. - Amino Acids and Peptides, XXXVIII. - Total Synthesis of the 10,11-Dihydrozizyphines A and B
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The 10,11-dihydrozizyphines A (13a) and B (15a) were synthesized.The cyclopeptide ring closure reactions were accomplished by catalytic hydrogenation of the linear ω-Z-amino acid pentafluorophenyl ester 8a.
- Schmidt, Ulrich,Boekens, Hilmar,Lieberknecht, Albrecht,Griesser, Helmut
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p. 1459 - 1467
(2007/10/02)
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