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Berlin Brandenburg

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  • 1
    Language: English
    In: Tetrahedron Letters, 20 June 2012, Vol.53(25), pp.3173-3177
    Description: A facile protocol toward several substituted 3-aryl-3,4,4a,10-tetrahydro-2 -anthracen-9-ones starting with substituted 2-allylbenzaldehydes was described. The overall synthetic process was carried out by the domino aldol condensation/Diels–Alder cycloaddition of skeleton with substituted cinnamaldehydes in an alkalic aqueous-methanolic solution followed by base-induced double migration of the resulting cycloadducts. Skeleton was prepared from isovanillin ( ) in moderate yield in five-steps via the known procedures with the synthetic sequence of O-allylation, Claisen rearrangement, O-methylation, Grignard methylation, and PCC-mediated oxidation.
    Keywords: Claisen Rearrangement ; Aldol Condensation ; Diels–Alder Cycloaddition ; One-Pot Combination ; Tetrahydroanthracen-9-Ones ; Chemistry
    ISSN: 0040-4039
    E-ISSN: 1873-3581
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  • 2
    Language: English
    In: Tetrahedron, 25 November 2012, Vol.68(47), pp.9616-9623
    Description: A novel synthetic route for the preparation of cyclohexane skeleton was developed via the one-pot domino Claisen–Schmidt condensation reaction/Michael addition/double aldol reaction of 1 equiv of functionalized arylaldehyde with 3 equiv of 2-acetylpyridine ( ).
    Keywords: Condensation ; Arylaldehyde ; 2-Acetylpyridine ; Cyclohexane ; Chemistry
    ISSN: 0040-4020
    E-ISSN: 1464-5416
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  • 3
    Language: English
    In: Tetrahedron, 05 August 2012, Vol.68(31), pp.6224-6230
    Description: Four benzodioxepanes – were prepared from reaction of 4-methoxy-3-hydroxybenzaldehyde via a series of reasonable transformations, including the regioselective PhBCl -mediated double allylation of , one-pot combination of ring-closing metathesis of skeleton and Baeyer–Villiger reaction, O-allylation of skeleton , Claisen rearrangement of skeleton , and one-pot combination of ring-closing metathesis and hydrogenation.
    Keywords: Benzodioxapane ; Ortho-Metalation ; Ring-Closing Metathesis ; Baeyer–Villiger Reaction ; Claisen Rearrangement ; O-Allylation ; Chemistry
    ISSN: 0040-4020
    E-ISSN: 1464-5416
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  • 4
    Language: English
    In: Tetrahedron, 07 January 2013, Vol.69(1), pp.129-136
    Description: A facile synthetic route toward diversified benzo[ ]chrysenes starting with commercially available isovanillin ( ) or 3-hydroxybenzaldehyde ( ) in modest total yields is described via the transformations of Claisen rearrangement of , Grignard addition of , DBU-promoted cyclodehydration of , and photolytic Scholl oxidative annulation of . Skeleton is prepared via O-allylation of with -cinnamyl bromide.
    Keywords: Benzo[G]Chrysenes ; Claisen Rearrangement ; Grignard Addition ; Cyclodehydration ; Photolytic Scholl Oxidative Annulation ; Chemistry
    ISSN: 0040-4020
    E-ISSN: 1464-5416
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  • 5
    Language: English
    In: Tetrahedron Letters, 11 December 2013, Vol.54(50), pp.6971-6974
    Description: Synthesis of aryl biaryl sulfones with good yields is described. The one-pot efficient synthetic route is carried by the NaH-mediated tandem [C3+C3] annulations of cinnamaldehydes and propargylic sulfones under the boiling THF conditions.
    Keywords: One-Pot Synthesis ; Aryl Biaryl Sulfones ; Cinnamaldehydes ; Propargylic Sulfones ; Chemistry
    ISSN: 0040-4039
    E-ISSN: 1873-3581
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  • 6
    Language: English
    In: Tetrahedron Letters, 18 April 2012, Vol.53(16), pp.2125-2128
    Description: A facile three-step protocol toward methoxy isoquinolines starting with substituted 2-allylbenzaldehydes was described. The overall synthetic process of skeleton was carried out using the Grignard addition, PCC-oxidation, and one-pot oxidative cleavage of the olefinic group of skeleton with OsO –NaIO followed by the condensation of the resulting 1,5-dicarbonyl compounds with NH OAc. Skeleton was prepared in high yield via the known Claisen rearrangement of skeleton and O-methylation. Papaverine is also synthesized via the simple three-step synthetic protocol.
    Keywords: Isoquinoline ; Claisen Rearrangement ; One-Pot Combination Reaction ; Papaverine ; Chemistry
    ISSN: 0040-4039
    E-ISSN: 1873-3581
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  • 7
    In: PLoS ONE, 2015, Vol.10(10)
    Description: In this study, six 2-phenylnaphthalenes with hydroxyl groups were synthesized in high yields by the demethylation of the corresponding methoxy-2-phenylnaphthalenes, and one 2-phenylnaphthalene with an amino group was obtained by hydrogenation. All of the 2-phenylnaphthalene derivatives were evaluated for cytotoxicity, and the structure-activity relationship (SAR) against human breast cancer (MCF-7) cells was also determined. The SAR results revealed that cytotoxicity was markedly promoted by the hydroxyl group at the C-7 position of the naphthalene ring. The introduction of hydroxyl groups at the C-6 position of the naphthalene ring and the C-4 ' position of the phenyl ring fairly enhanced cytotoxicity, but the introduction of a hydroxyl group at the C-3 ' position of the phenyl ring slightly decreased cytotoxicity. Overall, 6,7-dihydroxy-2-(4'-hydroxyphenyl)naphthalene ( PNAP - 6h ) exhibited the best cytotoxicity, with an IC 50 value of 4.8 μM against the MCF-7 cell line, and showed low toxicity toward normal human mammary epithelial cells (MCF-10A). PNAP - 6h led to cell arrest at the S phase, most likely due to increasing levels of p21 and p27 and decreasing levels of cyclin D1, CDK4, cyclin E, and CDK2. In addition, PNAP - 6h decreased CDK1 and cyclin B1 expression, most likely leading to G 2 /M arrest, and induced morphological changes, such as nuclear shrinkage, nuclear fragmentation, and nuclear hypercondensation, as observed by Hoechst 33342 staining. PNAP - 6h induced apoptosis, most likely by the promotion of Fas expression, increased PARP activity, caspase-7, caspase-8, and caspase-9 expression, the Bax/Bcl-2 ratio, and the phosphorylation of p38, and decreased the phosphorylation of ERK. This study provides the first demonstration of the cytotoxicity of PNAPs against MCF-7 cells and elucidates the mechanism underlying PNAP-induced cytotoxicity.
    Keywords: Research Article
    E-ISSN: 1932-6203
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  • 8
    Language: English
    In: Tetrahedron, Sept 16, 2013, Vol.69(37), p.7916(9)
    Description: To link to full-text access for this article, visit this link: http://dx.doi.org/10.1016/j.tet.2013.07.023 Byline: Meng-Yang Chang, Chieh-Kai Chan, Ming-Hao Wu Abstract: A one-pot synthetic route for preparing functionalized p-terphenyl derivatives 1 and 4 is developed. The route is easily carried from the treatment of cinnamyl aldehydes 2 with substituted allylsulfones 3 in good yields via the tandem intermolecular aldol condensation/intramolecular electrocyclization/oxidative dehydrogenation. Author Affiliation: Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan Article History: Received 30 May 2013; Revised 3 July 2013; Accepted 8 July 2013
    Keywords: Dehydrogenation
    ISSN: 0040-4020
    Source: Cengage Learning, Inc.
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  • 9
    Language: English
    In: The Journal of organic chemistry, 04 April 2014, Vol.79(7), pp.3206-14
    Description: A diverse library of novel carbamates was synthesized utilizing copper-catalyzed oxidative C-O coupling of formamides and salicylaldehydes. Sensitive aldehyde groups remained intact in the presence of an oxidant and a transition-metal salt. Salicylaldehydes bearing electron-donating, electron-withdrawing, and halogen groups as well as 1-hydroxy-2-naphthaldehydes provided the desired carbamates in good to excellent yields.
    Keywords: Aldehydes -- Chemistry ; Carbamates -- Chemical Synthesis ; Copper -- Chemistry ; Formamides -- Chemistry
    ISSN: 00223263
    E-ISSN: 1520-6904
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  • 10
    Language: English
    In: PLoS ONE, 2012, Vol. 7(5), p. e37897
    Description: In a structure-activity relationship (SAR) study, 3-methoxy-1,4-phenanthrenequinones, calanquinone A (6a), denbinobin (6b), 5-OAc-calanquinone A (7a) and 5-OAc-denbinobin (7b), have significantly promising cytotoxicity against various human cancer cell lines (IC50 0.08-1.66 mu g/mL). Moreover, we also established a superior pharmacophore model for cytotoxicity (r = 0.931) containing three hydrogen bond acceptors (HBA1, HBA2 and HBA3) and one hydrophobic feature (HYD) against MCF-7 breast cancer cell line. The pharmacophore model indicates that HBA3 is an essential feature for the oxygen atom of 5-OH in 6a-b and for the carbonyl group of 5-OCOCH3 in 7a-b, important for their cytotoxic properties. The SAR for moderately active 5a-b (5-OCH3), and highly active 6a-b and 7a-b, are also elaborated in a spatial aspect model. Further rational design and synthesis of new cytotoxic phenanthrene analogs can be implemented via this model. Additionally, employing a ChemGPS-NP based model for cytotoxicity mode of action (MOA) provides support for a preliminary classification of compounds 6a-b as topoisomerase II inhibitors.
    Keywords: Medical And Health Sciences ; Medicin Och Hälsovetenskap
    ISSN: 1932-6203
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