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Journal articles on the topic 'Carbocyclic compounds'

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Author: Grafiati

Published: 7 September 2023

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 (May 3, 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. This review summarizes all these developments made since 2008 in the field of metal-catalyzed/promoted radical-mediated functionalization of ketones at the α-position.1 Introduction2 Synthesis of 1,4-Dicarbonyl Compounds3 Synthesis of Heterocyclic Scaffolds4 Synthesis of Carbocyclic Scaffolds5 Conclusion

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2

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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3

Biteau, Nicolas G., Sarah A. Amichai, Niloufar Azadi, Ramyani De, Jessica Downs-Bowen, Julia C. Lecher, Tamara MacBrayer, Raymond F. Schinazi, and Franck Amblard. "Synthesis of 4′-Substituted Carbocyclic Uracil Derivatives and Their Monophosphate Prodrugs as Potential Antiviral Agents." Viruses 15, no. 2 (February 16, 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, influenza A/B viruses and norovirus.

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4

Ando, Wataru. "Polyorganosilicon Compounds in Strained Carbocyclic Systems." Bulletin of the Chemical Society of Japan 69, no. 1 (January 1996): 1–16. http://dx.doi.org/10.1246/bcsj.69.1.

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5

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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6

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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7

Halimehjani, Azim Ziyaei, Irishi N. N. Namboothiri, and Seyyed Emad Hooshmand. "Nitroalkenes in the synthesis of carbocyclic compounds." RSC Advances 4, no. 59 (June 24, 2014): 31261. http://dx.doi.org/10.1039/c4ra04069d.

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8

Bartulewic, D., A. Markowska, S. Wołczyński, M. Dabrowska, and A. Rózański. "Molecular modelling, synthesis and antitumour activity of carbocyclic analogues of netropsin and distamycin--new carriers of alkylating elements." Acta Biochimica Polonica 47, no. 1 (March 31, 2000): 23–35. http://dx.doi.org/10.18388/abp.2000_4059.

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A series of netropsin and distamycin analogues was synthesised and investigated by molecular modelling. The lowest-energy conformations of four carbocyclic lexitropsins, potential carriers of alkylating elements, were obtained using the HyperChem 4.0 program, and compared with the DNA-lexitropsin crystal structures from the Brookhaven National Laboratory Protein Data Bank. A method for synthesis of carbocyclic lexitropsins was elaborated, with the use of a nitro group or azobenzene as precursors for the aromatic amino group. The influence of methoxy group in ortho position with respect to amide groups on the activity of the new compounds was investigated. All of the compounds tested showed high antitumour activity in the standard cell line of mammalian tumour MCF-7.

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9

Niu, Ben, Yin Wei, and Min Shi. "Recent advances in annulation reactions based on zwitterionic π-allyl palladium and propargyl palladium complexes." Organic Chemistry Frontiers 8, no. 13 (2021): 3475–501. http://dx.doi.org/10.1039/d1qo00273b.

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Carbocyclic and heterocyclic compounds could be constructed through the palladium-catalyzed annulation reactions of zwitterionic π-allyl palladium or propargyl palladium complexes with unsaturated electrophiles.

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10

Liu, Yuxiao, Yu Liu, Charles S. Shanahan, Xichen Xu, and Michael P. Doyle. "A survey of enoldiazo nucleophilicity in selective C–C bond forming reactions for the synthesis of natural product-like frameworks." Org. Biomol. Chem. 12, no. 28 (2014): 5227–34. http://dx.doi.org/10.1039/c4ob00709c.

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11

Morikawa, Tetsuo. "Graph-Theoretical Enumeration of Conjugated Patterns for Carbocyclic and Heterocyclic Compounds*." Zeitschrift für Naturforschung A 49, no. 3 (March 1, 1994): 511–14. http://dx.doi.org/10.1515/zna-1994-0310.

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Abstract An algorithmic analysis of the existence of conjugated patterns for carbocyclic and heterocyclic compounds is presented. This graph theoretical method is applicable to the enumeration of Kekulé patterns for hydrocarbon benzenoids, as a special case.

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12

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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13

Zhang, Tao, Zi-Yu Zhang, Guowei Kang, Tao Sheng, Jie-Lun Yan, Yuan-Bin Yang, Yuxin Ouyang, and Jin-Quan Yu. "Enantioselective remote methylene C−H (hetero)arylation of cycloalkane carboxylic acids." Science 384, no. 6697 (May 17, 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 enantioselective editing of two methylene C–H bonds can be achieved by using chiral ligands with opposite configuration to construct carbocycles containing three chiral centers. Enantioselective remote δ-C−H (hetero)arylation is also realized to establish δ-stereocenters that are particularly challenging to access using classical methodologies.

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14

Chen, Houguang Jeremy, Ronald Hong Xiang Teo, Jonathan Wong, Yongxin Li, Sumod A. Pullarkat, and Pak-Hing Leung. "Challenges in cyclometalation: steric effects leading to competing pathways and η1,η2-cyclometalated iridium(iii) complexes." Dalton Transactions 47, no. 37 (2018): 13046–51. http://dx.doi.org/10.1039/c8dt02639d.

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The iridation of a known cyclometalating ligand led to several products, one of which is an olefin-directed carbocyclic iridacycle. The mechanistic pathways to the formation of these compounds were investigated.

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15

Barbera, J., E. Melendez, J. L. Serrano, M. T. Sierra, A. Ezcurra, and M. A. Perez Jubindo. "Chiral Mesogenic Compounds: Carbocyclic and Heterocyclic Schiff Bases." Molecular Crystals and Liquid Crystals Incorporating Nonlinear Optics 170, no. 1 (May 1989): 151–57. http://dx.doi.org/10.1080/00268948908047755.

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16

ANDO, W. "ChemInform Abstract: Polyorganosilicon Compounds in Strained Carbocyclic Systems." ChemInform 27, no. 17 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199617312.

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17

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 (May 1, 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, benzyl amines, hydrazones, and triazines.

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18

Pućkowska, Anna, Krzysztof Bielawski, Anna Bielawska, and Andrzej Rózański. "New carbocyclic analogues of netropsin: synthesis and inhibition of topoisomerases." Acta Biochimica Polonica 49, no. 1 (March 31, 2002): 177–83. http://dx.doi.org/10.18388/abp.2002_3834.

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A series of carbocyclic analogues of netropsin were synthesized and evaluated for their capacity to inhibit human topoisomerases I and II in vitro. The compounds are oligopeptides containing 1,4-di- and 1,2,5-trisubstituted benzene rings and unsubstituted N-terminal NH2 groups. Compounds 4-7 consist of two netropsin-like units linked by aliphatic (tetra- and hexamethylene) chains. In the topoisomerase I and II assay, the relaxation of pBR322 plasmid was inhibited by compounds 4-7 at 100 microM concentration.

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19

Andrés, Patricia, Gema Ballano, M. Isabel Calaza, and Carlos Cativiela. "Synthesis of α-aminoboronic acids." Chemical Society Reviews 45, no. 8 (2016): 2291–307. http://dx.doi.org/10.1039/c5cs00886g.

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This review provides an overview of methodologies for the synthesis of acyclic, carbocyclic and azacyclic α-aminoboronic acid derivatives. Preparation routes towards these challenging compounds in either their racemic or their enantiomerically pure form are discussed.

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20

Doraghi, Fatemeh, Mohammad Mahdi Aghanour Ashtiani, Fatemeh Moradkhani, Bagher Larijani, and Mohammad Mahdavi. "Developments and applications of α-bromonitrostyrenes in organic syntheses." RSC Advances 14, no. 21 (2024): 14835–46. http://dx.doi.org/10.1039/d4ra02474e.

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In this work, we have described the use of α-bromonitrostyrenes in the synthesis of a wide variety of carbocyclic and heterocyclic compounds under organocatalysis, metal catalysis, and base-catalysis systems as well as catalyst-free reactions.

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21

Battistini, Lucia, Claudio Curti, Gloria Rassu, Andrea Sartori, and Franca Zanardi. "Enolizable Alkylidene Heterocyclic and Carbocyclic Carbonyl Systems: Valuable Vinylogous Donor Substrates in Synthesis." Synthesis 49, no. 11 (April 6, 2017): 2297–336. http://dx.doi.org/10.1055/s-0036-1589487.

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Controlled vinylogous carbon–carbon bond-forming reactions are useful options for providing the selective remote functionalization of conjugated carbonyl substrates. Remotely enolizable alkylidene heterocyclic and carbocyclic carbonyl compounds are pro-nucleophilic substrates that may be engaged in highly valuable chemical transformations. This review emphasizes the merits of these recently discovered vinylogous donors in the chemo-, regio- and stereoselective synthesis of many functionality-rich products.1 Introduction2 Alkylidene Oxindoles3 Alkylidene Pyrazolinones4 Alkylidene Furanones5 Alkylidene Azlactones6 Cycloalkylidene Carbonyl Compounds7 Alkylidene Indenones8 Cycloalkylidene Malononitriles9 Conclusion

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22

Erian, Ayman W., Yvette A. Issac, and Sherif M. Sherif. "A Novel Synthesis of Sulfone Systems as Antimicrobial Agents." Zeitschrift für Naturforschung B 55, no. 1 (January 1, 2000): 127–32. http://dx.doi.org/10.1515/znb-2000-0119.

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The applicability and synthetic potency of novel reagent, 2-aryl-1,1-dicyano-3-(phenylsulfo-nyl)propenes 3 to develop an expeditious convenient synthetic route of unique polyfunctionally substituted carbocyclic and heterocyclic sulfone systems is reported. Chemical and spectroscopic evidence for the structures of the newly synthesized compounds are described. Some of the obtained compounds were tested for their antimicrobial activity

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23

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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24

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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25

Shinde, Madhuri V., Rohini S. Ople, Ekta Sangtani, Rajesh Gonnade, and D. Srinivasa Reddy. "Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction." Beilstein Journal of Organic Chemistry 11 (June 23, 2015): 1060–67. http://dx.doi.org/10.3762/bjoc.11.119.

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A novel and convenient method utilizing the Aubé reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aubé reaction with various cyclic ketones to give cyclopentenyl-substituted lactams. Upon dihydroxylation, this affords the N-cyclopentenyl-lactam compounds in racemic form. Given the numerous uses of nucleosides and related compounds, we were interested in the synthesis of carbocylic nucleoside mimics. The attempts and results are described herein.

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26

Quadrelli, Paolo, Naiara Vazquez Martinez, Roberto Scrocchi, Antonino Corsaro, and Venerando Pistarà. "Syntheses of Isoxazoline-Carbocyclic Nucleosides and Their Antiviral Evaluation: A Standard Protocol." Scientific World Journal 2014 (2014): 1–12. http://dx.doi.org/10.1155/2014/492178.

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The current synthesis of racemic purine and pyrimidine isoxazoline-carbocyclic nucleosides is reported, detailing the key-steps for standard and reliable preparations. Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds. Some of the obtained compounds were also evaluated against a wide variety of DNA and RNA viruses including HIV. No specific antiviral activity was observed in the cases at hand. Novel compounds were prepared for future biological tests.

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27

Zhou, Jian, Guannan Wang, Li-He Zhang, and Xin-Shan Ye. "From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds." Current Organic Chemistry 10, no. 6 (April 1, 2006): 625–42. http://dx.doi.org/10.2174/138527206776359711.

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28

TADANO, Kin-ichi, and Tetsuo SUAMI. "Chiral synthesis of alkaloids and carbocyclic compounds from carbohydrates." Journal of Synthetic Organic Chemistry, Japan 44, no. 7 (1986): 633–46. http://dx.doi.org/10.5059/yukigoseikyokaishi.44.633.

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29

Halimehjani, Azim Ziyaei, Irishi N. N. Namboothiri, and Seyyed Emad Hooshmand. "ChemInform Abstract: Nitroalkenes in the Synthesis of Carbocyclic Compounds." ChemInform 45, no. 47 (November 6, 2014): no. http://dx.doi.org/10.1002/chin.201447261.

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30

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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31

Morikawa, Tetsuo. "Structural Features for Non-Existence of Conjugated Patterns for Carbocyclic and Heterocyclic Compounds." Zeitschrift für Naturforschung A 49, no. 6 (June 1, 1994): 719–22. http://dx.doi.org/10.1515/zna-1994-0611.

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Abstract At least one polygonal arc (a′ a a′), where (a′) and (a) denote unconjugated and conjugated vertices (connected with two vertices), respectively, is involved implicitly and/or explicitly in a skeleton of carbocyclic and heterocyclic compounds with no side-chains, if the number of conjugated vertices is even, and if there is no conjugated structure. This case is discussed in detail.

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32

Jiang, Yue-Ming, Jie Liu, Qiang Fu, Yu-Ming Yu, and Da-Gang Yu. "Visible-Light-Driven Phosphonoalkylation of Alkenes." Synlett 32, no. 04 (February 12, 2021): 378–82. http://dx.doi.org/10.1055/s-0040-1706681.

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AbstractPhosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

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33

Arciszewska, Karolina, Anna Pućkowska, Agnieszka Wróbel, and Danuta Drozdowska. "Carbocyclic Analogues of Distamycin and Netropsin." Mini-Reviews in Medicinal Chemistry 19, no. 2 (December 6, 2018): 98–113. http://dx.doi.org/10.2174/1389557518666181009143203.

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The DNA as the depository of genetic information is a natural target for chemotherapy. A lot of anticancer and antimicrobial agents derive their biological activity from their selective interaction with DNA in the minor groove and from their ability to interfere with biological processes such as enzyme catalysis, replication and transcription. The discovery of the details of minor groove binding drugs, such as netropsin and distamycin A, oligoamides built of 4-amino-1-methylpyrrole-2-carboxylic acid residues, allowed to develop various DNA sequence-reading molecules, named lexitropsins, capable of interacting with DNA precisely, strongly and with a high specificity, and at the same time exhibiting significant cytotoxic potential. Among such compounds, lexitropsins built of carbocyclic sixmembered aromatic rings occupy a quite prominent place in drug research. This work is an attempt to present current findings in the study of carbocyclic lexitropins, their structures, syntheses and biological investigations such as DNA-binding and antiproliferative activity.

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34

Lakeev, Sergei N., Irina O. Maydanova, Fanur Z. Galin, and Genrikh A. Tolstikov. "Sulfur ylides in the synthesis of heterocyclic and carbocyclic compounds." Russian Chemical Reviews 70, no. 8 (August 31, 2001): 655–72. http://dx.doi.org/10.1070/rc2001v070n08abeh000645.

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35

Savoia, Diego, Giuseppe Falini, and Andrea Gualandi. "Rhodium/Graphite-Catalyzed Hydrogenation of Carbocyclic and Heterocyclic Aromatic Compounds." Synthesis 2009, no. 14 (June 2, 2009): 2440–46. http://dx.doi.org/10.1055/s-0029-1216852.

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36

Keshavarz, Mohammad Hossein, and Hamid Reza Pouretedal. "New approach for predicting melting point of carbocyclic nitroaromatic compounds." Journal of Hazardous Materials 148, no. 3 (September 30, 2007): 592–98. http://dx.doi.org/10.1016/j.jhazmat.2007.03.014.

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37

Müllen, Klaus. "Book Review: Non-Benzenoid Conjugated Carbocyclic Compounds. By D. Lloyd." Angewandte Chemie International Edition in English 24, no. 11 (November 1985): 1007–8. http://dx.doi.org/10.1002/anie.198510072.

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38

Matyugina, E. S., S. N. Andreevskaya, T. G. Smirnova, and A. L. Khandazhinskaya. "Carbocyclic Analogues of Inosine-5’-Monophosphate: Synthesis and Biological Activity." Acta Naturae 4, no. 4 (December 15, 2012): 73–77. http://dx.doi.org/10.32607/20758251-2012-4-4-73-77.

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9-(4-Phosphonomethoxy-2-cyclopenten-1-yl)hypoxanthine and 9-(4-phosphonomethoxy-2,3-dihydroxycyclopenten-1-yl)hypoxanthine were synthesized as isosteric carbocyclic analogues of inosine-5-monophosphate. The synthesized compounds were shown to be capable of inhibiting the activity of human type II inosine-5-monophosphate dehydrogenase (IMPDH II) (IC50 = 500 M) and to have no significant effects on the growth of Mycobacterium tuberculosis.

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39

Hronowski, Lucjan J. J., and Walter A. Szarek. "Synthesis of cyclopentane analogs of (2′- and 3′-deoxy-erythro-pentofuranosyl and ribofuranosyl)-2-thiouracil nucleosides." Canadian Journal of Chemistry 64, no. 8 (August 1, 1986): 1620–29. http://dx.doi.org/10.1139/v86-268.

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Three new carbocyclic analogs of nucleosides having the 2-thiouracil base have been synthesized. The cyclopentyl groups in these nucleosides are (±)-{(1β,3α,4β)-3-hydroxy-4-(hydroxyrnethyl)cyclopentyl} (see 31), (±)-{(1β,2α,4β)-2-hydroxy-4-(hydroxymethyl)cyclopentyl} (see 32), and (±)-{(1β,2α,3α,4β)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl} (see 33). The nucleosides were prepared by coupling the appropriate hydroxy derivatives of cis-3-aminocyclopentanemethanol with 3-ethoxypropenoyl isothiocyanate (21) followed by cyclization in 15 N aqueous ammonia to give the 2-thiouracil nucleosides. In addition a modified and shortened synthetic route is described for the synthesis of (±)-(1β,2α,3α,4β)-4-amino-2,3-dihydroxy-cyclopentanemethanol (19). The 1H nmr spectra at 200 MHz of all of the synthetic intermediates, the 2-thiouracil nucleosides, and of the corresponding carbocyclic analogs of uracil nucleosides are discussed. It is shown that each nucleoside has a characteristically unique 1H nmr spectrum and that in general the protons in the sulfur-containing compounds resonate at lower fields than those in the corresponding oxygen-containing compounds. The magnitude of this downfield shift is inversely related to the number of bonds separating a particular proton from the sulfur atom.

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40

Hronowski, Lucjan J. J., and Walter A. Szarek. "Synthesis of cyclopentane analogs of 5-fluorouracil nucleosides." Canadian Journal of Chemistry 70, no. 4 (April 1, 1992): 1162–69. http://dx.doi.org/10.1139/v92-152.

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New carbocyclic analogs (12, 14, and 15) of 5-fluorouracil nucleosides have been prepared by fluorination, using elemental fluorine, of the acetylated analogs (8, 10, and 11, respectively) of 1-(2′,3′-dideoxy-glycero-pentofuranosyl)-and 1-(2′- and 3′-deoxy-β-threo-pentofuranosyl)-uracil nucleosides. The carbocyclic analog (14) of 1-(2′-deoxy-β-threo-pentofuranosyl)-5-fluorouracil was then utilized for the preparation of various new carbocyclic analogs of 1-(3′-substituted-2′,3′-dideoxy-β-erythro-pentofuranosyl)-5-fluorouracil nucleosides by SN2 displacement of the 3′-mesyloxy group in the protected derivative 17. In this way analogs having the chloro (see 23), bromo (see 24), and azido (see 25) groups at the 3′-position were obtained; the analog 29 having a 3′-amino group was obtained by reduction of the azido group. In addition (±)-5-fluoro-1-{3-(hydroxymethyl)-3-cyclopenten-1-yl}-2,4(1H,3H)-pyrimidinedione (26) was obtained as an elimination side-reaction product in the preparation of the 3′-chloro and 3′-bromo analogs. Compounds 8, 9, 12, 14, 15, 25, and 29 were tested against the herpes simplex viruses and were found to be inactive. Compound 26 inhibited the growth of K-562 cells with an ID50 (10−4–10−3), which was about 100-fold greater than that of 5-fluorouracil in this test system. Analogs 12, 25, and 29 were slightly cytotoxic.

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41

Kitamura, Masato, Kengo Miyata, Tomoaki Seki, Namdev Vatmurge, and Shinji Tanaka. "CpRu-catalyzed asymmetric dehydrative allylation." Pure and Applied Chemistry 85, no. 6 (April 15, 2013): 1121–32. http://dx.doi.org/10.1351/pac-con-12-10-02.

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Asymmetric Tsuji–Trost allylation is one of the key chiral technologies for construction of pharmaceutically important compounds because of the high utility of alkenyl-substituted products. Particularly, the dehydrative system using allylic alcohols and protic nucleophiles has started to attract the attention of organic synthetic chemists from the viewpoints of atom and step economy, environmental benignity, and operational simplicity. In this paper, two types of new chiral CpRu catalysts, which have been developed on the basis of redox-mediated donor–acceptor bifunctional catalyst (RDACat) concept, are presented. Complementary use of the chiral catalysts has realized the syntheses of a wide rage of carbocyclic compounds, saturated N- or O-heterocyclic compounds with high reactivity, regioselectivity, enantioselectivity, productivity, and generality.

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42

Durakov, S. A., A. A. Kolobov, and V. R. Flid. "Features of heterogeneous catalytic transformations of strained carbocyclic compounds of the norbornene series." Fine Chemical Technologies 17, no. 4 (September 30, 2022): 275–97. http://dx.doi.org/10.32362/2410-6593-2022-17-4-275-297.

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Objectives. Catalytic processes involving norbornene (NBN) and norbornadiene (NBD) offer exceptional opportunities for the synthesis of a wide range of hard-to-reach polycyclic hydrocarbons. The problems of selectivity and manufacturability of these reactions are fundamentally important for their practical implementation. The aim of this review is to summarize the latest advances in the field of designing heterogeneous catalysts for the preparation and transformation of promising NBN- and NBD-derivatives with the maintenance of a strained carbocyclic framework in isomerization and dimerization reactions of these compounds.Results. Various strategies for the selection of catalysts and prospects for the development of heterogeneous catalysis for syntheses based on NBN and NBD derivatives were considered. The possibility of selective cyclic dimerization and isomerization of NBN and NBD was shown. The factors that affect the direction of the reactions and make it possible to maintain the strained norbornane structure were discussed.Conclusions. An analysis of the current state of this problem showed that at present, the technological parameters of the conversion of NBD and NBN derivatives with the participation of heterogeneous catalysts are significantly inferior to homogeneous systems. In order to improve the productivity of these processes and design catalyst regeneration, further investigations are required. However, some progress in these areas has already been made. In a number of processes, it is possible not only to maintain the strained carbocyclic framework, but also to establish ways to control regio- and stereo-selectivity. In some cases, the use of heterogeneous catalysts allows the process to be direct into a completely new path, which has no analogues for homogeneous systems.

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43

Yang, De-Suo, Zheng-Hui Guan, Sen Ke, Ming-Jin Fan, Hai-Tao Zhu, and Xiao-Ling Wang. "A Facile and Efficient Synthesis of Six-Membered Enol Carbocyclic Compounds." Synlett 26, no. 20 (October 28, 2015): 2826–30. http://dx.doi.org/10.1055/s-0035-1560517.

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44

Gallos, John K., Zoe S. Massen, Theocharis V. Koftis, and Constantinos C. Dellios. "Carbocyclic nucleoside precursors by intramolecular cyclopropanation of sugar-derived diazo compounds." Tetrahedron Letters 42, no. 42 (October 2001): 7489–91. http://dx.doi.org/10.1016/s0040-4039(01)01556-8.

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45

Gutke, Hans-Jürgen, and Dietrich Spitzner. "Resin-bound anionically induced Domino reactions; synthesis of functionalized carbocyclic compounds." Tetrahedron 55, no. 13 (March 1999): 3931–36. http://dx.doi.org/10.1016/s0040-4020(99)00113-1.

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46

MARUYAMA, Tokumi, and Mitsutoshi FUKUHARA. "Synthesis and Antitumor Activity of Phenyl Carbocyclic Oxetanocin and Related Compounds." CHEMICAL & PHARMACEUTICAL BULLETIN 44, no. 7 (1996): 1407–11. http://dx.doi.org/10.1248/cpb.44.1407.

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47

DOLGII, I. E., V. G. BORDAKOV, O. B. VETROVA, G. A. GRIGOR'EVA, E. A. KATSMAN, O. M. NEFEDOV, V. N. PAVLYCHEV, N. V. TRESHCHALINA, and T. A. BORTYAN. "ChemInform Abstract: Preparation of Carbocyclic Compounds and Synthesis on Their Basis." ChemInform 25, no. 25 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199425313.

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48

Al-Saad, Dalya, Misal Giuseppe Memeo, and Paolo Quadrelli. "#Nitrosocarbonyls 1: Antiviral Activity ofN-(4-Hydroxycyclohex-2-en-1-yl)quinoline-2-carboxamide against the Influenza A Virus H1N1." Scientific World Journal 2014 (2014): 1–10. http://dx.doi.org/10.1155/2014/472373.

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Influenza virus flu A H1N1 still remains a target for its inhibition with small molecules. Fleeting nitrosocarbonyl intermediates are at work in a short-cut synthesis of carbocyclic nucleoside analogues. The strategy of the synthetic approaches is presented along with thein vitroantiviral tests. The nucleoside derivatives were tested for their inhibitory activity against a variety of viruses. Promising antiviral activities were found for specific compounds in the case of flu A H1N1.

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49

Hanessian, Stephen, Daljit S. Dhanoa, and Pierre L. Beaulieu. "Synthesis of carbocycles from ω-substituted α,β-unsaturated esters via radical-induced cyclizations." Canadian Journal of Chemistry 65, no. 8 (August 1, 1987): 1859–66. http://dx.doi.org/10.1139/v87-312.

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The intramolecular radical cyclization of ω-bromo α,β-unsaturated esters for the synthesis of carbocyclic compounds is described. The effect of carbon chain substituents, the bulk of the ester group, and the olefin geometry were examined. The highest level of stereoselectivity (trans/cis: 9/1) was achieved with the Z ester via an exo cyclization. The sequential radical cyclization of a dihalodienoate to give a cis-fused bicyclic structure is also described.

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50

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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