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Journal articles on the topic 'Carbocyclic'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 May 2024

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1

Murarka, Sandip, and Andrey Antonchick. "Metal-Catalyzed Oxidative Coupling of Ketones and Ketone Enolates." Synthesis 50, no. 11 (2018): 2150–62. http://dx.doi.org/10.1055/s-0037-1609715.

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Recent years have witnessed a significant advancement in the field of radical oxidative coupling of ketones towards the synthesis of highly useful synthetic building blocks, such as 1,4-dicarbonyl compounds, and biologically important heterocyclic and carbocyclic compounds. Besides oxidative homo- and cross-coupling of enolates, other powerful methods involving direct C(sp3)–H functionalizations of ketones have emerged towards the synthesis of 1,4-dicarbonyl compounds. Moreover, direct α-C–H functionalization of ketones has also allowed an efficient access to carbocycles and heterocycles. Thi

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2

Yuasa, Hideya, Monica M. Palcic та 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, № 12 (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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3

Aimon, Anthony, Louis J. Farrugia, and J. Stephen Clark. "Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling." Molecules 24, no. 14 (2019): 2654. http://dx.doi.org/10.3390/molecules24142654.

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A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reaction between a vinylic iodide and an aldehyde. Good yields of carbocyclic products were obtained from the reaction, but diastereomeric mixtures of allylic alcohols were produced. The cyclisation reaction was successful irrespective of the relative configuration of the stereogenic centres in the cyclisa

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4

Meier, Chris, Simon Weising, and Ilaria Torquati. "Stereoselective Synthesis of 1′,2′-cis-Disubstituted Carbocyclic ribo-Nucleoside Analogues." Synthesis 50, no. 06 (2017): 1264–74. http://dx.doi.org/10.1055/s-0036-1591732.

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Herein we disclose an efficient strategy for the convergent synthesis of 1′,2′-cis-disubstituted carbocyclic ribo-nucleoside analogues. Starting from an enantiomerically pure cyclopentenol precursor, the key step for the preparation of the highly functionalized carbocyclic building block is an asymmetric dihydroxylation. Employing different variants of the Mitsunobu protocol, the condensation with all-natural nucleobases or their precursors affords a series of ribo-configured carbocyclic 1′,2′-cis-disubstituted nucleoside analogues.

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5

Yin, Xueqiang, Guoxia Zhao, and Stewart W. Schneller. "Carbocyclic sinefungin." Tetrahedron Letters 48, no. 28 (2007): 4809–11. http://dx.doi.org/10.1016/j.tetlet.2007.05.079.

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6

Marquez, Victor E., and Mu-Ill Lim. "Carbocyclic nucleosides." Medicinal Research Reviews 6, no. 1 (1986): 1–40. http://dx.doi.org/10.1002/med.2610060102.

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7

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 (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 (38) 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 (68). 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 synthe

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8

Vince, Robert, Mei Hua, and Carol A. Caperelli. "PHOSPHONATE ANALOGS OF CARBOCYCLIC PHOSPHORIBOSYLAMINE AND CARBOCYCLIC GLYCINAMIDE RIBONUCLEOTIDE." Nucleosides and Nucleotides 15, no. 11-12 (1996): 1711–18. http://dx.doi.org/10.1080/07328319608002726.

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9

Slama, James T., Nimish Mehta та Ewa Skrzypczak-Jankun. "Carbocyclic Ribosylamines: Synthesis of 5-Substituted Carbocyclic β-Ribofuranosylamines". Journal of Organic Chemistry 71, № 20 (2006): 7877–80. http://dx.doi.org/10.1021/jo060920l.

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10

Zard, Samir Z. "The xanthate route to six-membered carbocycles." Journal of Chemical Research 46, no. 2 (2022): 174751982210881. http://dx.doi.org/10.1177/17475198221088194.

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Convergent routes to various six-membered carbocyclic architectures exploiting the unique radical chemistry of xanthates are described in this brief review. Three approaches are discussed. The first is the modification of existing cyclohexane building blocks, namely, cyclohexanones, cyclohexenones and cyclohexenes. The second deals with the construction of six-membered carbocycles by associating the chemistry of xanthates with classical ionic reactions, especially the Robinson annulation, the Michael addition and the Horner–Wadsworth–Emmons condensation. Finally, the third route is the formati

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11

Hegde, Vishnumurthy R., Katherine L. Seley, and Stewart W. Schneller. "Carbocyclic 5′-Noruridine." Nucleosides, Nucleotides and Nucleic Acids 19, no. 1-2 (2000): 269–73. http://dx.doi.org/10.1080/15257770008033008.

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12

Schneller, Stewart, Yan Zhang, Wei Ye, and Haisheng Wang. "Carbocyclic 4-Deazaformycins." Synthesis 44, no. 05 (2012): 723–30. http://dx.doi.org/10.1055/s-0031-1289688.

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13

Maier, Lukáš, Ondřej Hylse, Marek Nečas, et al. "New carbocyclic nucleosides: synthesis of carbocyclic pseudoisocytidine and its analogs." Tetrahedron Letters 55, no. 27 (2014): 3713–16. http://dx.doi.org/10.1016/j.tetlet.2014.05.030.

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14

Sidi Mohamed, Bemba, Christian Périgaud, and Christophe Mathé. "Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues." Beilstein Journal of Organic Chemistry 13 (February 9, 2017): 251–56. http://dx.doi.org/10.3762/bjoc.13.28.

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The racemic synthesis of new carbocyclic nucleoside methylphosphonate analogues bearing purine bases (adenine and guanine) was accomplished using bio-sourced furfuryl alcohol derivatives. All compounds were prepared using a Mitsunobu coupling between the heterocyclic base and an appropriate carbocyclic precursor. After deprotection, the compounds were evaluated for their activity against a large number of viruses. However, none of them showed significant antiviral activity or cytotoxicity.

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15

Meier, Chris, Simon Weising, Patrick Dekiert, Dominique Schols, and Johan Neyts. "Synthesis of Enantiomerically Pure 1′,2′-cis-dideoxy, -dideoxydidehydro, -ribo and -deoxy Carbocyclic Nucleoside Analogues." Synthesis 50, no. 11 (2018): 2266–80. http://dx.doi.org/10.1055/s-0037-1609493.

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We describe a short and stereospecific synthesis of different series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues. All-natural nucleobases or their precursors are coupled in a microwave-assisted Mitsunobu-type reaction with enantiomerically pure (1R,2S)-2-(benzyloxymethyl)cyclopent-3-enol. By modifying the cyclopentene scaffold, our synthetic strategy gives access to a series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues of the dideoxy (dd), dideoxydidehydro (d4) or the ribo series. The ribo series is synthesized in a more convenient way compared to a previous rou

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16

Zhang, Tao, Zi-Yu Zhang, Guowei Kang, et al. "Enantioselective remote methylene C−H (hetero)arylation of cycloalkane carboxylic acids." Science 384, no. 6697 (2024): 793–98. http://dx.doi.org/10.1126/science.ado1246.

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Stereoselective construction of γ- and δ-stereocenters in carbonyl compounds is a pivotal objective in asymmetric synthesis. Here, we report chiral bifunctional oxazoline-pyridone ligands that enable enantioselective palladium-catalyzed remote γ-C−H (hetero)arylations of free cycloalkane carboxylic acids, which are essential carbocyclic building blocks in organic synthesis. The reaction establishes γ-tertiary and α-quaternary stereocenters simultaneously in up to >99% enantiomeric excess, providing access to a wide range of cyclic chiral synthons and bioactive molecules. The sequential enan

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17

Biggadike, Keith, Alan D. Borthwick, Anne M. Exall, Barrie E. Kirk, Stanley M. Roberts, and Peter Youds. "Short convergent route to homochiral carbocyclic-2′-deoxynucleosides and carbocyclic ribonucleosides." J. Chem. Soc., Chem. Commun., no. 14 (1987): 1083–84. http://dx.doi.org/10.1039/c39870001083.

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18

VINCE, R., M. HUA, and C. A. CAPERELLI. "ChemInform Abstract: Phosphonate Analogues of Carbocyclic Phosphoribosylamine and Carbocyclic Glycinamide Ribonucleotide." ChemInform 28, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199738261.

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19

Akabane-Nakata, Masaaki, Tyler Chickering, Joel M. Harp, et al. "RNAs Containing Carbocyclic Ribonucleotides." Organic Letters 24, no. 2 (2021): 525–30. http://dx.doi.org/10.1021/acs.orglett.1c03936.

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20

Zhou, Jian, Minmin Yang, Akin Akdag, Haisheng Wang, and Stewart W. Schneller. "Carbocyclic 4′-epi-formycin." Tetrahedron 64, no. 2 (2008): 433–38. http://dx.doi.org/10.1016/j.tet.2007.10.054.

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21

Agrofoglio, Luigi, Edouard Suhas, Audrey Farese, et al. "Synthesis of carbocyclic nucleosides." Tetrahedron 50, no. 36 (1994): 10611–70. http://dx.doi.org/10.1016/s0040-4020(01)89258-9.

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22

Mévellec, Laurence, and François Huet. "Novel cyclobutane carbocyclic nucleosides." Tetrahedron 50, no. 46 (1994): 13145–54. http://dx.doi.org/10.1016/s0040-4020(01)89324-8.

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23

Öfele, K., E. Tosh, C. Taubmann, and W. A. Herrmann. "Carbocyclic Carbene Metal Complexes." Chemical Reviews 109, no. 8 (2009): 3408–44. http://dx.doi.org/10.1021/cr800516g.

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24

Palmer, Christopher F., Keith P. Parry, and Stanley M. Roberts. "Synthesis of carbocyclic clitocine." Tetrahedron Letters 31, no. 2 (1990): 279–82. http://dx.doi.org/10.1016/s0040-4039(00)94392-2.

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25

Legeret, B., Z. Sarakauskaite, F. Pradaux, Y. Saito, S. Tumkevicius, and L. A. Agrofoglio. "SYNTHESIS OF CARBOCYCLIC PHOSPHONONUCLEOSIDES." Nucleosides, Nucleotides and Nucleic Acids 20, no. 4-7 (2001): 661–64. http://dx.doi.org/10.1081/ncn-100002345.

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26

Tuncbilek#, Meral, and Stewart W. Schneller. "5′-Nor Carbocyclic Ribavirin." Nucleosides, Nucleotides and Nucleic Acids 22, no. 11 (2003): 1995–2001. http://dx.doi.org/10.1081/ncn-120026401.

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27

Cotter, Andrew, Una Ni Ghogain, and Mary J. Meegan. "CARBOCYCLIC ANALOGUES OF PENICILLINS." Journal of Pharmacy and Pharmacology 37, S12 (1985): 133P. http://dx.doi.org/10.1111/j.2042-7158.1985.tb14204.x.

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28

Biggadike, Keith, Alan D. Borthwick, Derek Evans, et al. "Synthesis of fluorinated carbocyclic nucleosides: preparation of (±)-carbocyclic-FMAU and some congeners." J. Chem. Soc., Chem. Commun., no. 4 (1987): 251–54. http://dx.doi.org/10.1039/c39870000251.

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29

Maier, Lukas, Ondrej Hylse, Marek Necas, et al. "ChemInform Abstract: New Carbocyclic Nucleosides: Synthesis of Carbocyclic Pseudoisocytidine and Its Analogues." ChemInform 45, no. 49 (2014): no. http://dx.doi.org/10.1002/chin.201449169.

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30

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 (2004): 1991–95. http://dx.doi.org/10.1055/s-2004-829141.

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31

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 t

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32

Boyd, Derek R., Narain D. Sharma, Ludmila V. Modyanova, et al. "Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems." Canadian Journal of Chemistry 80, no. 6 (2002): 589–600. http://dx.doi.org/10.1139/v02-062.

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Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihy dro diol metabolites using whole cells of Pseudomonas putida UV4. cis-Dihydroxylation at the 3,4-bond of 2-chloroquino line, 2-methoxyquinoline, and 2-quinolone was also found to yield the heterocyclic cis-dihydrodiol metabolite, (+)-cis-(3S,4S)-3,4-dihydroxy-3,4-dihydro-2-quinolone. Heterocyclic cis-dihydrodiol metabolites, resulting from dihydroxylation at the 5,6- and 3,4-bon

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33

Bartulewicz, D., K. Bielawski, A. Markowska, K. Zwierz, A. Pućkowska, and A. Rózański. "Synthetic analogues of netropsin and distamycin--synthesis of a new pyridine and carbocyclic analogues of the pyrrolecarboxamide antitumour antibiotics." Acta Biochimica Polonica 45, no. 1 (1998): 41–57. http://dx.doi.org/10.18388/abp.1998_4317.

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A new series of pyridine-containing analogues III-XXII of distamycin A and netrop sin was investigated by the molecular mechanics technique and molecular modelling. A pyridine analogue of netropsin (VII) is described, the first compound based on molecular studies, and two carbocyclic analogues of distamycin A with an N-terminal chloro- or bromoacetyl group (VIa, VIIa) were synthesized, as well as carbocyclic analogues of netropsin (VIIIb, Xb), potential carriers of alkylating elements. The potential use of VIa, VII, VIIa, VIIIb and Xb as carriers to place into the minor groove of DNA chemical

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34

Biteau, Nicolas G., Sarah A. Amichai, Niloufar Azadi, et al. "Synthesis of 4′-Substituted Carbocyclic Uracil Derivatives and Their Monophosphate Prodrugs as Potential Antiviral Agents." Viruses 15, no. 2 (2023): 544. http://dx.doi.org/10.3390/v15020544.

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Over the past decades, both 4′-modified nucleoside and carbocyclic nucleoside analogs have been under the spotlight as several compounds from either family showed anti-HIV, HCV, RSV or SARS-CoV-2 activity. Herein, we designed compounds combining these two features and report the synthesis of a series of novel 4′-substituted carbocyclic uracil derivatives along with their corresponding monophosphate prodrugs. These compounds were successfully prepared in 19 to 22 steps from the commercially available (-)-Vince lactam and were evaluated against a panel of RNA viruses including SARS-CoV-2, influe

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35

Al Mamari, Hamad H. "Ir-Catalyzed ortho-C-H Borylation of Aromatic C(sp2)-H Bonds of Carbocyclic Compounds Assisted by N-Bearing Directing Groups." Reactions 5, no. 2 (2024): 318–37. http://dx.doi.org/10.3390/reactions5020016.

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C-H borylation is a powerful strategy for the construction of C-B bonds due to the synthetic versatility of C-B bonds. Various transition metals affect the powerful functionalization of C-H bonds, of which Ir is the most common. Substrate-directed methods have enabled directed Ir-catalyzed C-H borylation at the ortho position. Amongst the powerful directing groups in Ir-catalyzed C-H borylation are N-containing carbocyclic systems. This review covers substrate-directed Ir-catalyzed ortho-C-H borylation of aromatic C(sp2)-H bonds in N-containing carbocyclic compounds, such as anilines, amides,

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36

Barkley, James V., Anupma Dhanda, May-Britt Nielsen, Stanley M. Roberts, Lars J. S. Knutsen, and David R. Varley. "Stereoselective conversion of 2′,3′-dideoxydidehydro carbocyclic nucleosides into 2′-deoxy carbocyclic nucleosides." Chemical Communications, no. 10 (1998): 1117–18. http://dx.doi.org/10.1039/a801759j.

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37

Halder, Joydev, Debabrata Das та 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, № 14 (2018): 2549–75. http://dx.doi.org/10.1039/c8ob00233a.

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38

Hu, Hui-Juan, Peng Chen, Yu-Fei Ao, Qi-Qiang Wang, De-Xian Wang, and Mei-Xiang Wang. "Highly efficient biocatalytic desymmetrization of meso carbocyclic 1,3-dicarboxamides: a versatile route for enantiopure 1,3-disubstituted cyclohexanes and cyclopentanes." Organic Chemistry Frontiers 6, no. 6 (2019): 808–12. http://dx.doi.org/10.1039/c9qo00069k.

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39

Samunuri, Ramakrishnamraju, Masaaki Toyama, Renuka Sivasankar Pallaka, et al. "Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin." RSC Medicinal Chemistry 11, no. 5 (2020): 597–601. http://dx.doi.org/10.1039/d0md00059k.

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40

Jandl, Christian, and Alexander Pöthig. "A hybrid carbocyclic/N-heterocyclic carbene ligand." Chemical Communications 53, no. 13 (2017): 2098–101. http://dx.doi.org/10.1039/c6cc08468k.

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41

Gao, Yuan, Xiaonan Wang, Zhonglin Wei, et al. "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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42

Wermuth, Camille G. "Are pyridazines privileged structures?" MedChemComm 2, no. 10 (2011): 935–41. http://dx.doi.org/10.1039/c1md00074h.

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43

Sidi Mohamed, Bemba, Christian Périgaud, Suzanne Peyrottes, Jean-Pierre Uttaro, and Christophe Mathé. "Rapid synthesis of carbonucleoside phophonate analogues as potential antiviral agents via a hydrophosphonylation reaction of ethynyl carbocyclic precursors." New Journal of Chemistry 42, no. 2 (2018): 974–79. http://dx.doi.org/10.1039/c7nj03991c.

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44

Xie, Ming-Sheng, Yong Wang, Jian-Ping Li та ін. "A straightforward entry to chiral carbocyclic nucleoside analogues via the enantioselective [3+2] cycloaddition of α-nucleobase substituted acrylates". Chemical Communications 51, № 62 (2015): 12451–54. http://dx.doi.org/10.1039/c5cc04832j.

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45

Gaber, Hatem M., Mark C. Bagley, Zeinab A. Muhammad, and Sobhi M. Gomha. "Recent developments in chemical reactivity of N,N-dimethylenamino ketones as synthons for various heterocycles." RSC Advances 7, no. 24 (2017): 14562–610. http://dx.doi.org/10.1039/c7ra00683g.

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46

Vila, Carlos, Arturo Tortosa, Gonzalo Blay, M. Carmen Muñoz, and José R. Pedro. "Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines." New Journal of Chemistry 43, no. 1 (2019): 130–34. http://dx.doi.org/10.1039/c8nj05577g.

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47

Ojeda-Porras, A. C., V. Roy, O. Bourzikat, P. Favetta, and L. A. Agrofoglio. "Cobalt-assisted route to rare carbocyclic C-ribonucleosides." RSC Advances 13, no. 44 (2023): 30777–86. http://dx.doi.org/10.1039/d3ra04937j.

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48

W. Schneller, Stewart, Jayu Wu, Katherine L. Seley, and Erik De Clercq. "Carbocyclic 7-Deazaguanine Oxetanocin Analogues." HETEROCYCLES 47, no. 2 (1998): 757. http://dx.doi.org/10.3987/com-97-s(n)63.

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49

Elliott, Robert D., Gregory A. Rener, James M. Riordan, et al. "Phosphonate Analogs of Carbocyclic Nucleotides." Journal of Medicinal Chemistry 37, no. 6 (1994): 739–44. http://dx.doi.org/10.1021/jm00032a006.

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50

Csuk, René, and Yvonne von Scholz. "Synthesis of cyclopropyl carbocyclic nucleosides." Tetrahedron 50, no. 35 (1994): 10431–42. http://dx.doi.org/10.1016/s0040-4020(01)89583-1.

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