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Journal articles on the topic 'Carbocyclic ring synthesis'

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Published: 4 June 2021
Last updated: 16 February 2022

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1

KILBURN, J. D. "ChemInform Abstract: Saturated Carbocyclic Ring Synthesis." ChemInform 26, no. 3 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199503271.

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2

KILBURN, J. D. "ChemInform Abstract: Saturated Carbocyclic Ring Synthesis." ChemInform 25, no. 45 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199445282.

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3

KILBURN, J. D. "ChemInform Abstract: Saturated Carbocyclic Ring Synthesis." ChemInform 23, no. 32 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199232265.

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4

KILBURN, J. "ChemInform Abstract: Saturated Carbocyclic Ring Synthesis." ChemInform 24, no. 10 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199310303.

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5

LEE, T. V. "ChemInform Abstract: Saturated Carbocyclic Ring Synthesis." ChemInform 22, no. 25 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199125277.

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6

Liu, Peng, and Chung K. Chu. "Enantiomeric synthesis of carbocyclic analogs of D- and L-6-azapyrimidine ribonucleosides." Canadian Journal of Chemistry 84, no. 4 (April 1, 2006): 748–54. http://dx.doi.org/10.1139/v06-052.

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An effective and practical synthesis of carbocyclic D- and L-6-azapyrimidine nucleosides (3–8) was described. Starting from D-ribose, a new efficient methodology for the synthesis of L-2,3-O-cyclohexylidene-4-cyclopentenone (23) was developed via a ring-closing metathesis, which was applied for the synthesis of L-cyclopentyl-6-azapyrimidine nucleosides (6–8). The regiospecific introduction of 6-azauracil on the carbocyclic moiety (9 and 25) was also achieved by masking its N3 position with a 4-methylthio group.Key words: carbocyclic nucleosides, 6-azapyrimidine nucleosides, enantiomeric synthesis.
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7

Yuasa, Hideya, Monica M. Palcic, and Ole Hindsgaul. "Synthesis of the carbocyclic analog of uridine 5′-(α-D-galactopyranosyl diphosphate) (UDP-Gal) as an inhibitor of β(1 → 4)-galactosyltransferase." Canadian Journal of Chemistry 73, no. 12 (December 1, 1995): 2190–95. http://dx.doi.org/10.1139/v95-272.

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Uridine 5′-(5a-carba-α-D-galactopyranosyl diphosphate), the carbocyclic analog of UDP-galactose where the ring oxygen of the galactose residue is replaced by a methylene group, was chemically synthesized as a potential inhibitor of galactosyltransferases. It was found to be a competitive inhibitor of UDP-galactose: N-acetylglucosamine β(1 → 4)-galactosyltransferase from bovine milk (EC 2.4.1.22) with a Ki value of 58 µM, similar to the Km value for UDP-galactose (25 µM). Keywords: carbocycles, UDP-5a-carbagalactose, galactosyltransferase, glycosyltransferase inhibitor.
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8

Yamatoya, Y., M. Ishikura, and N. Katagiri. "Synthesis of carbocyclic nucleosides bearing a cyclopropane ring." Nucleic Acids Symposium Series 42, no. 1 (November 1, 1999): 23–24. http://dx.doi.org/10.1093/nass/42.1.23.

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9

Griffith, Daniel R., and Aaron H. Shoemaker. "Synthetic Approaches to Non-Tropane, Bridged, Azapolycyclic Ring Systems Containing Seven-Membered Carbocycles." Synthesis 53, no. 01 (September 11, 2020): 65–78. http://dx.doi.org/10.1055/s-0040-1707385.

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AbstractThis Short Review highlights various synthetic approaches to bridged azabicyclic ring systems containing seven-membered carbocyclic rings. Such ring systems are common to a number of biologically active natural products. The seven-membered ring in such systems is generally formed in one of four ways: 1) cyclization of an acyclic precursor; 2) ring expansion or rearrangement of a different ring size; 3) cycloaddition; and 4) use of a synthetic building block with the seven-membered ring already present. Representative examples of each approach from both total synthesis and methodological studies are discussed, with an emphasis on work publishedin the last twenty years.1 Introduction2 Cyclization Reactions3 Ring Expansions and Rearrangements4 Cycloadditions5 Strategies Involving Seven-Membered Ring Building Blocks6 Conclusion
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10

Gao, Yuan, Xiaonan Wang, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, and Haifeng Duan. "Asymmetric synthesis of spirooxindole–pyranoindole products via Friedel–Crafts alkylation/cyclization of the indole carbocyclic ring." New Journal of Chemistry 44, no. 23 (2020): 9788–92. http://dx.doi.org/10.1039/d0nj00074d.

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11

Lautens, Mark, Dino Alberico, Cyril Bressy, Yuan-Qing Fang, Brian Mariampillai, and Thorsten Wilhelm. "Palladium-catalyzed ring-forming reactions: Methods and applications." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 351–61. http://dx.doi.org/10.1351/pac200678020351.

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Several Pd-catalyzed cyclization methods were developed, including norbornene-mediated Catellani-type reactions, a Pd-catalyzed coupling reaction of aryl iodides and allyl moieties, and a tandem C-N/C-C coupling of gem-dihalovinyl systems. These ring-forming methods were applied to the synthesis of highly functionalized carbocyclic and heterocyclic compounds. Intermolecular Pd-catalyzed methods for synthesis of highly substituted arene compounds were also developed.
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12

Yavari, Issa, and Aliyeh Khajeh-Khezri. "Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds­ and Complexes Based on Acenaphthylene-1,2-dione." Synthesis 50, no. 20 (August 16, 2018): 3947–73. http://dx.doi.org/10.1055/s-0037-1610209.

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Acenaphthylene-1,2-dione has been utilized in a wide range of reactions as a starting material for the synthesis of hetero- and carbocyclic compounds and complexes. This review provides a short summary of the recent advances in the application of acenaphthylene-1,2-dione in the synthesis of hetero- and carbocyclic systems and bioactive compounds. In addition, the applications of acenaphthylene-1,2-dione in the synthesis of spiro compounds, propellanes, and ligands in catalyst reactions, from 2002 to early 2018, are included.1 Introduction2 Synthesis of Spiro Compounds Employing Acenaphthylene-1,2-dione2.1 Methods for the Construction of Spiro Compounds2.1.1 By 1,3-Dipolar Cycloaddition of Acenaphthylene-1,2-dione via Azomethine Ylides2.1.2 By Multicomponent Reactions of Acenaphthylene-1,2-dione with C–H Acidic Compounds2.1.3 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates2.1.4 By Substitution and Multicomponent Reactions of Acenaphth- ylene-1,2-dione with Different Nucleophiles3 Synthesis of Propellanes by Employing Acenaphthylene-1,2-dione3.1 Methods for the Construction of Propellanes Based on Acenaph- thylene-1,2-dione3.1.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles3.1.2 By Reaction of Acenaphthylene-1,2-dione with Binucleophiles4 Synthesis of Ligands Employing Acenaphthylene-1,2-dione for Catalyst Reactions5 Synthesis of Novel Hetero- and Carbocyclic Compounds Employing Acenaphthylene-1,2-dione5.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles5.2 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates5.3 By Ring Opening and Ring Enlargement6 Conclusion
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13

Halder, Joydev, Debabrata Das, and Samik Nanda. "A distinctive transformation based diversity oriented synthesis of small ring carbocycles and heterocycles from biocatalytically derived enantiopure α-substituted-β-hydroxyesters." Organic & Biomolecular Chemistry 16, no. 14 (2018): 2549–75. http://dx.doi.org/10.1039/c8ob00233a.

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14

van Lierop, Bianca J., Christoph Bornschein, W. Roy Jackson, and Andrea J. Robinson. "Ring-closing Metathesis in Peptides - the Sting is in the Tail!" Australian Journal of Chemistry 64, no. 6 (2011): 806. http://dx.doi.org/10.1071/ch11090.

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Performing ring-closing metathesis on resin-bound peptides provides an expedient route to carbocyclic peptidomimetics of medicinal interest. Some sequences are highly resistant to metathesis and special strategies need to be employed to promote viable ring closure. This paper describes an on-resin, alternating solid-phase peptide synthesis-catalysis method to overcome deleterious aggregation phenomena. It can be used to promote high yielding single-ring closures and regioselective multi-ring construction in peptides.
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15

Banwell, MG. "New Methods for the Synthesis of Troponoid Compounds." Australian Journal of Chemistry 44, no. 1 (1991): 1. http://dx.doi.org/10.1071/ch9910001.

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The ring expansion of 7-halogenobicyclo[4.1.0] heptenones and related compounds provides a useful new method for the preparation of the seven-membered conjugated carbocyclic compounds known as tropones and tropolones. This methodology has been exploited in the synthesis of various biologically active troponoid natural products including nezukone, the thujaplicins, thujaplicinol, MY3-469 and colchicine.
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16

Sunkara, Naresh K., Sylvester L. Mosley, and Katherine L. Seley-Radtke. "A Carbocyclic 7-Deazapurine-Pyrimidine Hybrid Nucleoside." Collection of Czechoslovak Chemical Communications 71, no. 8 (2006): 1161–68. http://dx.doi.org/10.1135/cccc20061161.

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The design, synthesis and rationale for the first example of a carbocyclic 7-deazapurine- pyrimidine hybrid nucleoside is described. The marriage of key structural features from the purine and pyrimidine nucleobase scaffolds has given rise to novel hybrid nucleobases designed to be recognized by biologically relevant purine- and pyrimidine-metabolizing enzymes. Pairing these hybrid bases with chemotherapeutically beneficial carbocyclic "sugars", in addition to utilizing the highly effective 7-deaza ring system, should result in chemotherapeutically useful nucleosides. The approach to realize the first 7-deazapurine-pyrimidine hybrid nucleoside3is presented herein.
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17

Halliday, Jill I., Mary Chebib, and Malcolm D. McLeod. "Synthesis and Biological Evaluation of a New Family of Constrained Azabicyclic Homocholine Analogues." Australian Journal of Chemistry 63, no. 5 (2010): 808. http://dx.doi.org/10.1071/ch10024.

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A family of constrained acylated homocholine analogues have been synthesized, based on the azabicyclic ring scaffold derived from a double-Mannich annulation of cyclic ketones. The short synthetic route allows generation of structural diversity including, variation in the carbocyclic ring size, bridgehead substitution, nitrogen substitution and the ester sidechain. Biological assays on selected analogues demonstrate these compounds are nicotinic acetylcholine receptor (nAChR) antagonists. Several analogues also bind to other neuronal transporter and receptor targets.
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18

Fernández, Franco, María Figueira, Olga Caamaño, J. Rodríguez-Borges, Jan Balzarini, and Erik De Clercq. "Synthesis and Biological Evaluation of Carbocyclic Nucleosides with 2′,3′-Dihomo-xylo-carbocyclic or Carbocyclic Fused to a Tetrahydrofuran Ring." Synthesis 2004, no. 12 (July 13, 2004): 1991–95. http://dx.doi.org/10.1055/s-2004-829141.

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19

Breder, Alexander, Gary M Chinigo, Andrew W Waltman, and Erick M Carreira. "Enantioselective Synthesis of the Carbocyclic D-Ring Subunit of Massadine." Angewandte Chemie 120, no. 44 (October 20, 2008): 8642–45. http://dx.doi.org/10.1002/ange.200803284.

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20

Breder, Alexander, Gary M Chinigo, Andrew W Waltman, and Erick M Carreira. "Enantioselective Synthesis of the Carbocyclic D-Ring Subunit of Massadine." Angewandte Chemie International Edition 47, no. 44 (October 20, 2008): 8514–17. http://dx.doi.org/10.1002/anie.200803284.

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21

Kim, Hak Sung, and Kenneth A. Jacobson. "Synthesis of a Novel Conformationally Locked Carbocyclic Nucleoside Ring System." Organic Letters 5, no. 10 (May 2003): 1665–68. http://dx.doi.org/10.1021/ol034326z.

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22

Remete, Attila Márió, and Loránd Kiss. "Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs." Molecules 24, no. 1 (January 3, 2019): 161. http://dx.doi.org/10.3390/molecules24010161.

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Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino alcohols with 5-amino-4,6-dichloropyrimidine; ring closure of the formed adduct with HC(OMe)3 and nucleophilic displacement of chlorine with various N-nucleophiles in the resulting 6-chloropurine moiety.
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23

Saborit, Gisela V., Carlos Cativiela, Ana I. Jiménez, Josep Bonjoch, and Ben Bradshaw. "Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation." Beilstein Journal of Organic Chemistry 14 (October 9, 2018): 2597–601. http://dx.doi.org/10.3762/bjoc.14.237.

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A straightforward synthetic entry to functionalized hydrindane compounds based on a rapid assembly of the core nucleus by a Danheiser cycloaddition is reported. Valuable bicyclic building blocks containing the fused five and six-membered carbocyclic ring system can be achieved in only four steps from a simple acyclic β-keto ester.
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24

Gahman, Timothy C., and Larry E. Overman. "Stereoselective synthesis of carbocyclic ring systems by pinacol-terminated Prins cyclizations." Tetrahedron 58, no. 32 (August 2002): 6473–83. http://dx.doi.org/10.1016/s0040-4020(02)00658-0.

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25

Salim, Sofia S., Richard K. Bellingham, Vachiraporn Satcharoen, and Richard C. D. Brown. "Synthesis of Heterocyclic and Carbocyclic Fluoro-olefins by Ring-Closing Metathesis." Organic Letters 5, no. 19 (September 2003): 3403–6. http://dx.doi.org/10.1021/ol035065w.

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26

Trost, Barry M., Zhongxing Huang, and Ganesh M. Murhade. "Catalytic palladium-oxyallyl cycloaddition." Science 362, no. 6414 (November 1, 2018): 564–68. http://dx.doi.org/10.1126/science.aau4821.

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Exploration of intermediates that enable chemoselective cycloaddition reactions and expeditious construction of fused- or bridged-ring systems is a continuous challenge for organic synthesis. As an intermediate of interest, the oxyallyl cation has been harnessed to synthesize architectures containing seven-membered rings via (4+3) cycloaddition. However, its potential to access five-membered skeletons is underdeveloped, largely due to the thermally forbidden (3+2) pathway. Here, the combination of a tailored precursor and a Pd(0) catalyst generates a Pd-oxyallyl intermediate that cyclizes with conjugated dienes to produce a diverse array of tetrahydrofuran skeletons. The cycloaddition overrides conventional (4+3) selectivity by proceeding through a stepwise pathway involving a Pd-allyl transfer and ring closure sequence. Subsequent treatment of the (3+2) adducts with a palladium catalyst converts the heterocycles to the carbocyclic cyclopentanones.
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27

Memeo, Misal Giuseppe, Mariella Mella, and Paolo Quadrelli. "The Chemoselective Reduction of Isoxazolineγ-Lactams Through Iminium Aza-Diels-Alder Reactions: A Short-Cut Synthesis of Aminols as Valuable Intermediates towards Nucleoside Derivatives." Scientific World Journal 2012 (2012): 1–10. http://dx.doi.org/10.1100/2012/643647.

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Isoxazolineγ-lactams are prepared starting from the regioisomeric cycloadducts of benzonitrile oxide to theN-alkyl 2-azanorbornenes taking advantage of the efficient catalytic oxidation by RuO4. The reduction of the amide groups is easily conducted in the presence of LiAlH4under mild conditions, which allowed for the chemoselective reduction of the amide moiety followed by ring opening to afford the desired conformationally locked isoxazoline-carbocyclic aminols, as valuable intermediates for nucleoside synthesis.
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28

Csuk, René, Petra Dörr, Martin Kühn, Claus Krieger, and Mikhael Y. Antipin. "Chiral Pool Synthesis of 4a-Substituted Carbocyclic Cyclopentanoid Nucleoside Precursors, I." Zeitschrift für Naturforschung B 54, no. 8 (August 1, 1999): 1068–78. http://dx.doi.org/10.1515/znb-1999-0816.

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A suitable protected D-ribono-1,4-lactone derivative has been used for the straightforward chiral pool synthesis of cyclopentanoid nucleoside precursors. Thus, epoxidation followed by deoxygenation or regioselective ring opening led to nucleoside precursors modified at the positions C(4), C(4a) and C(4,4a) as well as side-chain modified derivatives. The structures of the key intermediates were determined by X-ray analyses.
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29

Isobe, Minoru. "Conjugate addition approach for natural product synthesis inspired by gibberellin and solanoeclepin A targets." Pure and Applied Chemistry 85, no. 6 (March 18, 2013): 1149–60. http://dx.doi.org/10.1351/pac-con-12-10-07.

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Trimethylzincate is known to react through conjugate addition to α,β-unsaturated ketones, but adds much faster to α,β-unsaturated esters at low temperatures. Since the intermediate zinc enolate behaves differently from that of dimethylcuprate, it offers scope for application in a partial synthesis of gibberellin A3. A second example involving vinylsulfones having an oxygen atom on the γ-carbon strongly directs incoming nucleophiles in conjugate addition mode. Heteroatom-directed conjugate addition (HADCA) provides very reactive carbanion intermediates leading to cyclobutane ring formation, necessary for synthesis of solanoeclepin A. An alternative reaction for the four-membered carbocyclic ring closure was explored to make a bond formation between the propargylic cation of Nicholas type and allyltrimethylsilane nucleophile of Hosomi–Sakurai type. This method allowed a formation of tricyclo[5.2.1.01,6]decene framework.
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30

Luisier, Samuel, and Christian J. Leumann. "Synthesis of Bicyclo-DNA Nucleosides with Additional Functionalization in the Carbocyclic Ring." CHIMIA International Journal for Chemistry 62, no. 4 (April 30, 2008): 270–72. http://dx.doi.org/10.2533/chimia.2008.270.

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31

Balo, Carmen, JoséM Blanco, Franco Fernández, Evangelina Lens, and Carmen López. "Synthesis of novel carbocyclic nucleosides with a cyclopentenyl ring: Homocarbovir and analogues." Tetrahedron 54, no. 12 (March 1998): 2833–42. http://dx.doi.org/10.1016/s0040-4020(98)83020-2.

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32

Mulamoottil, Varughese A., Akshata Nayak, and Lak Shin Jeong. "Recent Advances in the Synthesis of Carbocyclic Nucleosides via Ring-Closing Metathesis." Asian Journal of Organic Chemistry 3, no. 7 (May 9, 2014): 748–61. http://dx.doi.org/10.1002/ajoc.201402032.

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33

Clark, J. Stephen, Frederic Marlin, Bastien Nay, and Claire Wilson. "Synthesis of the Carbocyclic Core of the Cornexistins by Ring-Closing Metathesis." Organic Letters 5, no. 1 (January 2003): 89–92. http://dx.doi.org/10.1021/ol027265y.

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34

Takahashi, Hidetoshi, Kazuhiro Yoshida, and Akira Yanagisawa. "Synthesis of Carbocyclic Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis." Journal of Organic Chemistry 74, no. 10 (May 15, 2009): 3632–40. http://dx.doi.org/10.1021/jo900456g.

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35

Sivakrishna, Balija, Sehbanul Islam, Amarendra Panda, Maddi Saranya, Manas K. Santra, and Shantanu Pal. "Synthesis and Anticancer Properties of Novel Truncated Carbocyclic Nucleoside Analogues." Anti-Cancer Agents in Medicinal Chemistry 18, no. 10 (January 23, 2019): 1425–31. http://dx.doi.org/10.2174/1871520618666180322120533.

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Background: Modified nucleosides established a prime role as therapeutic drugs. Objective: Design and synthesis of novel truncated carbocyclic nucleoside with modified nucleobases and evaluation of their anticancer properties. Methods: Novel truncated carbocyclic nucleoside analogues were synthesized from a versatile starting material D-ribose. The synthetic route includes stereoselective Grignard reaction, Wittig olefination, ring closing metathesis, double bond hydrogenation and Mitsunobu nucleobase condensation as the key steps. Cytotoxicity was measured using MTT assay in breast cancer cell lines (MCF7 and MDA-MB-231), ovarian cancer cell lines (IGROV1 and OVCAR8). Result & Conclusion: The synthesized compounds were characterized using spectroscopy techniques. The synthesized compounds induced cytotoxicity in breast cancer cell lines (MCF7 and MDA-MB-231), ovarian cancer cell lines (IGROV1 and OVCAR8) while minimal effect on primary cell line. Among the eight analogues, 1b and 1d showed the highest cytotoxicity effect and induced autophagy mode of cell death. These compounds induced autophagy by inactivating AKT and mTOR pathway. In addition, PARP1 was found to be stabilized upon treatment with compound 1b and 1d and is one of the known markers associated with induction of autophagy through the AMPK/mTOR pathway after DNA damage. Taken together, these results suggest that compounds 1b and 1d inhibit cancer cell proliferation through mTOR inactivation-mediated induction of autophagy.
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36

Sridhar, Perali R., Vennam D. K. Reddy, Mandava Suresh, Nadiveedhi M. Reddy, and K. Shiva Kumar. "Synthesis of Carbocyclic Nucleosides (+)-Neplanocin A, (+)-Aristeromycin and 4'-epi-(+)-Aristeromycin from D-Fructose." Letters in Organic Chemistry 16, no. 9 (July 5, 2019): 750–58. http://dx.doi.org/10.2174/1570178615666181023145502.

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D-Fructose is used as the chiral pool starting material for the stereoselective total synthesis of (+)-neplanocin A. Zinc mediated fragmentation, ring-closing metathesis and oxidative rearrangement of cyclic tertiary allylic alcohol are used as the key steps in achieving the synthesis of key carbocylic intermediate. Further, stereoselective total synthesis of 4'-epi-(+)-aristeromycin and the conversion of (+)-neplanocin A to a mixture of (+)-aristeromycin and 4'-epi-(+)-aristeromycin are described.
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37

Rogers, Daniel H., Barbara Frey, Francis S. Roden, Friedrich-Wilhelm Russkamp, Anthony C. Willis, and Lewis N. Mander. "Exploratory Studies on the Synthesis of the Unusual Diterpenoid Tropone Harringtonolide." Australian Journal of Chemistry 52, no. 11 (1999): 1093. http://dx.doi.org/10.1071/ch99093.

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Various approaches to the total synthesis of the unusual diterpenoid tropone (2), discovered in the yew species Cephalotaxus harringtonia and C. hainanensis, are described. The rhodium-catalysed intramolecular cyclopropanation reaction of an aryl ring by means of the transition metal catalysed reaction of a diazoacetyl function was used to assemble the 5/7 ring system and to provide a cycloheptatrienyl precursor to the tropone moiety, e.g.(28)→(29) and (38) →(39). In the most promising approach, the carbocyclic system was assembled by means of the aldol reaction (42) →(43) with the newly formed α-hydroxyl being employed subsequently in the formation of the δ-lactone function of (44). The tropone ring may be formed from the methoxycycloheptatriene moiety simply by treatment with mercuric nitrate. Tropone (45) was formed from (44) in this way, but attempts to convert it into harringtonolide by means of transannular oxidation based on the 4-hypoiodite failed. The crystal structure of an intermediate is reported.
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38

Gahman, Timothy C., and Larry E. Overman. "ChemInform Abstract: Stereoselective Synthesis of Carbocyclic Ring Systems by Pinacol-Terminated Prins Cyclizations." ChemInform 33, no. 50 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200250061.

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39

Hirai, Sho, Masayuki Utsugi, Mitsuhiro Iwamoto, and Masahisa Nakada. "Formal Total Synthesis of (−)-Taxol through Pd-Catalyzed Eight-Membered Carbocyclic Ring Formation." Chemistry - A European Journal 21, no. 1 (October 24, 2014): 355–59. http://dx.doi.org/10.1002/chem.201404295.

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40

Ashfeld, Brandon L., and Zachary D. Tucker. "(4+1)-Cycloadditions Exploiting the Biphilicity of Oxyphosphonium Enolates and RhII/PdII-Stabilized Metallocarbenes for the Construction of Five-Membered Frameworks." Synlett 32, no. 12 (January 26, 2021): 1157–68. http://dx.doi.org/10.1055/s-0040-1706009.

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Abstract(4+1)-Cyclizations are an underutilized disconnect for the formation of five-membered heterocyclic and carbocyclic frameworks. Herein we analyze methods employing oxyphosphonium enolates and RhII/PdII-metallocarbenes as C1 synthons in the presence of several four-atom components for the synthesis of 2,3-dihydrobenzofurans, 2,3-dihydroindoles, oxazolones, cyclopentenones, and pyrrolones.1 Introduction2 (4+1)-Cyclizations Employing Kukhtin–Ramirez-Like Reactivity3 (4+1)-Cyclizations Employing a Cyclopropanation/Ring-Expansion Sequence4 Pd-Catalyzed (4+1)-Cyclizations through Carbene Migratory Insertion/Reductive Elimination Processes5 Summary
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41

Liboska, Radek, Milena Masojídková, and Ivan Rosenberg. "Carbocyclic Phosphonate-Based Nucleotide Analogs Related to PMEA. I. Racemic trans-Configured Derivatives." Collection of Czechoslovak Chemical Communications 61, no. 2 (1996): 313–32. http://dx.doi.org/10.1135/cccc19960313.

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Racemic trans-N-(2-phosphonomethoxycycloalkyl) derivatives of heterocyclic bases, a novel type of nucleotide analogs related to 9-(2-phosphonomethoxyethyl)adenine (PMEA), are reported. The synthesis of fully protected adenine- (5), hypoxanthine- (7), guanine- (11), thymine- (13), uracil- (16) and cytosine-containing (18) carbocyclic nucleotide analogs is based on the reaction of trans-2-hydroxycycloalkyl derivatives of N-protected nucleobases (2, 10, 12, 14, 17) with diisopropyl tosyloxymethanephosphonate. Deprotection of these compounds afforded the title nucleotide analogs. The starting nucleoside derivatives have been prepared via nucleophilic oxirane ring opening of cycloalkene oxides with various protected or free nucleobases.
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42

Ko, Ok Hyun, and Joon Hee Hong. "Efficient synthesis of novel carbocyclic nucleosides via sequential Claisen rearrangement and ring-closing metathesis." Tetrahedron Letters 43, no. 36 (September 2002): 6399–402. http://dx.doi.org/10.1016/s0040-4039(02)01384-9.

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43

Gooding, H., Stanley M. Roberts, and Richard Storer. "Synthesis of some carbocyclic nucleoside analogues based on a bicyclo[3.1.0]hexane ring system." Journal of the Chemical Society, Perkin Transactions 1, no. 14 (1994): 1891. http://dx.doi.org/10.1039/p19940001891.

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44

BALO, C., J. M. BLANCO, F. FERNANDEZ, E. LENS, and C. LOPEZ. "ChemInform Abstract: Synthesis of Novel Carbocyclic Nucleosides with a Cyclopentenyl Ring: Homocarbovir and Analogues." ChemInform 29, no. 29 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199829285.

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45

Mulamoottil, Varughese A., Akshata Nayak, and Lak Shin Jeong. "ChemInform Abstract: Recent Advances in the Synthesis of Carbocyclic Nucleosides via Ring-Closing Metathesis." ChemInform 45, no. 37 (August 28, 2014): no. http://dx.doi.org/10.1002/chin.201437266.

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46

Figueira, M. José, J. Manuel Blanco, Olga Caamaño, Franco Fernández, Xerardo García-Mera, Carmen López, Graciela Andrei, et al. "Synthesis and Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclobutane Ring." Archiv der Pharmazie 332, no. 10 (October 1999): 348–52. http://dx.doi.org/10.1002/(sici)1521-4184(199910)332:10<348::aid-ardp348>3.0.co;2-h.

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47

Sedlmaier, Helmut, Franz Müller, Paul J. Keller, and Adelbert Bacher. "Enzymatic Synthesis of Riboflavin and FMN Specifically Labeled with 13C in the Xylene Ring." Zeitschrift für Naturforschung C 42, no. 4 (April 1, 1987): 425–29. http://dx.doi.org/10.1515/znc-1987-0416.

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The condensation of 3-hydroximino-2-butanone (1) with 5-amino-6-ribitylamino-2,4(1H,3H)- pyrimidinedione (2) yields 6,7-dimethyl-8-ribityllumazine (3). At slightly alkaline pH, the car­bonyl group of 1 reacts preferentially with the 5-amino group of 2 (regioselectivity, 4:1). Under acidic conditions, the reaction occurs with higher yield and marginal regioselectivity of opposite direction (1:1.4). Appropriately 13C-labeled samples of 1 afford 3 labeled at C-6α, C-6, C-7 or C-7α. [6α,7α-13C2]-3 was prepared by condensation of 2 with [1,4-13C2]diacetyl. The lumazines 3 were converted to riboflavin by the enzyme, riboflavin synthase, with almost quantitative yield. By this procedure, any C-atom of the carbocyclic moiety of riboflavin can be selectively labeled with 13C at high abundance. Phosphorylation yields the respectively 13C-labeled FMN samples.
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48

Liboska, Radek, Milena Masojídková, and Ivan Rosenberg. "Carbocyclic Phosphonate-Based Nucleotide Analogs Related to PMEA II. Racemic cis-Configured Derivatives." Collection of Czechoslovak Chemical Communications 61, no. 5 (1996): 778–90. http://dx.doi.org/10.1135/cccc19960778.

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Racemic N-(cis-2-phosphonomethoxycycloalkyl) derivatives of heterocyclic bases, a novel type of nucleotide analogs related to 9-(2-phosphonomethoxyethyl)adenine (PMEA), are reported. The synthesis of adenine- (6a, 6b), uracil- (6c) and cytosine- (6d) containing carbocyclic phosphonates is based on the reaction of cis-2-hydroxycycloalkyl derivatives of protected nucleobases with diisopropyl tosyloxymethanephosphonate. The starting purine-containing nucleoside analogs 5a-5f were prepared by the Mitsunobu reaction of protected nucleobases with trans-2-benzyloxycycloalkanols, whereas pyrimidine-containing nucleoside analogs 5g-5k were obtained by configurational inversion at C-2' of the corresponding 1-(trans-2-hydroxycycloalkyl)pyrimidines via ring opening of their 2,2'-anhydro derivatives.
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49

Harrowven, David, Wei Sun, and Dharyl Wilson. "Steric Buttressing Changes Torquospecificity in Thermal Cyclo­butenone Rearrangements, Providing New Opportunities for 5H-Furanone Synthesis." Synthesis 49, no. 14 (June 13, 2017): 3091–106. http://dx.doi.org/10.1055/s-0036-1588850.

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Thermally induced rearrangements of 4-hydroxycyclo­butenones are known to provide clean and reliable access to an array of useful carbocyclic and fused heterocyclic ring systems. Rarely, such reactions have been diverted to an alternative pathway leading to furanone formation. Herein, we show that these switches in the course of the rearrangement occur when a substrate bears a bulky substituent and are due to adverse steric buttressing as the transition state for electrocyclisation is approached. We also show how the reaction provides new opportunities for furanone synthesis and how bulky proton and halogen surrogates can be used to divert classical rearrangement pathways toward furanone formation. Additionally, we show that classical rearrangement pathways can be promoted by the simple expedient of alcohol protection.
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50

Ito, Hisanaka, Takeo Taguchi, and Yuji Hanzawa. "Zirconium-mediated ring contraction: An efficient synthesis of enantiomerically pure key intermediate of carbocyclic oxetanocin." Tetrahedron Letters 34, no. 47 (November 1993): 7639–40. http://dx.doi.org/10.1016/s0040-4039(00)60421-5.

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