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Academic literature on the topic 'Macrocyclic cyclophanes'

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Published: 4 June 2021

Last updated: 12 February 2022

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Journal articles on the topic "Macrocyclic cyclophanes"

Collins, Shawn K., and Yassir El-Azizi. "Development of quadrupolar engaging auxiliaries as novel gearing elements for macrocyclization." Pure and Applied Chemistry 78, no. 4 (January 1, 2006): 783–89. http://dx.doi.org/10.1351/pac200678040783.

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The formation of various macrocyclic cyclophanes via ring-closing olefin metathesis is possible through the use of a pendant pentafluorobenzyl ester group. A quadrupolar interaction between the cyclophane core and the auxiliary is proposed to act as a gearing element facilitating cyclization. The development of these noncovalent interactions as gearing elements as well as the investigation of the effect of the site of metathesis upon the macrocyclization process is described.

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Salazar-Medina, Alex J., Enrique F. Velazquez-Contreras, Rocio Sugich-Miranda, Hisila Santacruz, Rosa E. Navarro, Fernando Rocha-Alonzo, Maria A. Islas-Osuna, et al. "Immune response of human cultured cells towards macrocyclic Fe2PO and Fe2PC bioactive cyclophane complexes." PeerJ 8 (April 20, 2020): e8956. http://dx.doi.org/10.7717/peerj.8956.

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Synthetic molecules that mimic the function of natural enzymes or molecules have untapped potential for use in the next generation of drugs. Cyclic compounds that contain aromatic rings are macrocyclic cyclophanes, and when they coordinate iron ions are of particular interest due to their antioxidant and biomimetic properties. However, little is known about the molecular responses at the cellular level. This study aims to evaluate the changes in immune gene expression in human cells exposed to the cyclophanes Fe2PO and Fe2PC. Confluent human embryonic kidney cells were exposed to either the cyclophane Fe2PO or Fe2PC before extraction of RNA. The expression of a panel of innate and adaptive immune genes was analyzed by quantitative real-time PCR. Evidence was found for an inflammatory response elicited by the cyclophane exposures. After 8 h of exposure, the cells increased the relative expression of inflammatory mediators such as interleukin 1; IRAK, which transduces signals between interleukin 1 receptors and the NFκB pathway; and the LPS pattern recognition receptor CD14. After 24 h of exposure, regulatory genes begin to counter the inflammation, as some genes involved in oxidative stress, apoptosis and non-inflammatory immune responses come into play. Both Fe2PO and Fe2PC induced similar immunogenetic changes in transcription profiles, but equal molar doses of Fe2PC resulted in more robust responses. These data suggest that further work in whole animal models may provide more insights into the extent of systemic physiological changes induced by these cyclophanes.

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Monchaud, David, Anton Granzhan, Nicolas Saettel, Aurore Guédin, Jean-Louis Mergny, and Marie-Paule Teulade-Fichou. "“One Ring to Bind Them All”—Part I: The Efficiency of the Macrocyclic Scaffold for G-Quadruplex DNA Recognition." Journal of Nucleic Acids 2010 (2010): 1–19. http://dx.doi.org/10.4061/2010/525862.

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Macrocyclic scaffolds are particularly attractive for designing selective G-quadruplex ligands essentially because, on one hand, they show a poor affinity for the “standard” B-DNA conformation and, on the other hand, they fit nicely with the external G-quartets of quadruplexes. Stimulated by the pioneering studies on the cationic porphyrin TMPyP4 and the natural product telomestatin, follow-up studies have developed, rapidly leading to a large diversity of macrocyclic structures with remarkable-quadruplex binding properties and biological activities. In this review we summarize the current state of the art in detailing the three main categories of quadruplex-binding macrocycles described so far (telomestatin-like polyheteroarenes, porphyrins and derivatives, polyammonium cyclophanes), and in addressing both synthetic issues and biological aspects.

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Seliger, Piotr, Danuta Tomczyk, Grzegorz Andrijewski, and Ewa Tomal. "The Determination of Protonation Constants of Peptidomimetic Cyclophanes in Binary Methanol-Water Mixtures." Journal of Analytical Methods in Chemistry 2016 (2016): 1–7. http://dx.doi.org/10.1155/2016/1721069.

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The protonation constants of new group of peptidomimetic cyclophanes with valine or phenylalanine moieties incorporated into the macrocyclic skeleton as well as their linear analogues were determined by potentiometric measurements in solutions of methanol-water mixtures at 25°C and constant ionic strength. The influence of cavity size, location of protonation sites, and attached substituents of the macrocyclic ligands on the protonation constants were discussed on the basis of potentiometric measurement as well as H1-NMR results.

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Liu, Zhichang, Siva Krishna Mohan Nalluri, and J. Fraser Stoddart. "Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes." Chemical Society Reviews 46, no. 9 (2017): 2459–78. http://dx.doi.org/10.1039/c7cs00185a.

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Heerklotz, Joerg A., Changchun Fu, Anthony Linden, and Manfred Hesse. "ChemInform Abstract: Photochemical Ring Enlargement of Macrocyclic N-Phenyl Imides into Cyclophanes." ChemInform 31, no. 47 (November 21, 2000): no. http://dx.doi.org/10.1002/chin.200047157.

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Esteve, Ferran, Belen Altava, Michael Bolte, M. Isabel Burguete, Eduardo García-Verdugo, and Santiago V. Luis. "Highly Selective Anion Template Effect in the Synthesis of Constrained Pseudopeptidic Macrocyclic Cyclophanes." Journal of Organic Chemistry 85, no. 2 (December 20, 2019): 1138–45. http://dx.doi.org/10.1021/acs.joc.9b03048.

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Murakami, Yukito, Osamu Hayashida, and Yasuyuki Nagai. "Hybrid molecular assemblies in combinations of a synthetic peptide lipid with macrocyclic cyclophanes." Recueil des Travaux Chimiques des Pays-Bas 113, no. 4 (September 2, 2010): 209–15. http://dx.doi.org/10.1002/recl.19941130408.

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Bedi, Anjan, Linda J. W. Shimon, Benny Bogoslavsky, and Ori Gidron. "Easier to Twist than Bend: The Scope of the Bridge Formation Approach to Naphthalenophane Synthesis." Organic Materials 02, no. 04 (October 2020): 323–29. http://dx.doi.org/10.1055/s-0040-1721102.

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Twisting anthracene and higher acenes can alter their optical, magnetic, and electronic properties. To test the effect of twisting on the lower homologue, naphthalene, we synthesized tethered naphthalenophanes bearing alkyl bridges. Both X-ray structure and DFT calculations show that hexyl and butyl bridges induce a 6° and 12° end-to-end twist on the naphthalene unit, respectively. Attempts to increase the twisting further using shorter tethers resulted in an elimination product. Enantiomerically pure naphthalenophanes display strong chiroptical properties, which intensify with increasing twist. Attempts to induce bending, rather than twisting, using the same synthetic methodology, resulted in intermolecular dimerization, yielding macrocyclic naphthalenes. This work highlights the importance of steric hindrance in the synthesis of curved cyclophanes using the bridge formation approach.

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Miyake, Yoshihiro, Mo Wu, M. Jalilur Rahman, Yoshiyuki Kuwatani, and Masahiko Iyoda. "Efficient Construction of Biaryls and Macrocyclic Cyclophanes via Electron-Transfer Oxidation of Lipshutz Cuprates." Journal of Organic Chemistry 71, no. 16 (August 2006): 6110–17. http://dx.doi.org/10.1021/jo0608063.

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Dissertations / Theses on the topic "Macrocyclic cyclophanes"

Thibault, Michelle Elizabeth, and University of Lethbridge Faculty of Arts and Science. "Novel bis(isobenzofuran)s and their utility in the synthesis of cyclophanes." Thesis, Lethbridge, Alta. : University of Lethbridge, Faculty of Arts and Science, 2003, 2003. http://hdl.handle.net/10133/239.

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The synthesis of 1,2-bis(5-isobenzofuranyl)ethene by two routes is described. The first route involved generation of 1,2-bis(5-isobenzofuranyl)ethene from a bis(acetal) precursor under basic conditions. However, the synthesis was lengthy with low-yielding steps, which led to it being abandoned. The second route involved generation of 1,2-bis(5-isobenzofuranyl)ethene from a bis(oxabicyclic) precursor with 3,6-di(2'-pyridyl)-s-tetrazine. Napththo[1,2-c:5,6-c] difuran and 1,2-bis(5isobenzofuranyl)ethene were used to construct novel cyclophanes by double Diels-Alder reactions with bis(maleimide)s. NMR, AM1 modeling, and X-ray studies of the cyclophanes are discused. Attempts to prepare phenanthro[2,3-c:6,7-c] difuran and its cyclophanes are discussed. None was successful, and investigations were hampered by the inability to obtain sufficient quantities of starting materials. Finally, several suggestions are given for improving the syntheses of 1,2-bis(5- isobenzofuranyl)ethene, phenanthro[2,3-c:6,7-c]difuran, and their cyclophanes. Future directions, such as the functionalization of the double bond of 1,2-bis(5-isobenzofuranyl)ethene, aromatization of the oxabicyclic rings of the cyclophanes, and further X-ray studies are discussed.
x, 122 leaves : ill. ; 28 cm.

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Dikmans, Antonius Josephus. "Synthesis of belt-shaped macrocyclic cyclophanes, Part I, synthesis of key intermediates in the proposed synthesis of (7)- and (8)cyclacenes, Part II, synthesis of key intermediates in a proposed synthesis of a cyclic decaphenylene." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1998. http://www.collectionscanada.ca/obj/s4/f2/dsk2/ftp02/NQ31119.pdf.

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Spenst, Peter [Verfasser], and Frank [Gutachter] Würthner. "Xylylene Bridged Perylene Bisimide Cyclophanes and Macrocycles / Peter Spenst ; Gutachter: Frank Würthner." Würzburg : Universität Würzburg, 2016. http://d-nb.info/1141054272/34.

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Florian, Maria Carmen. "Design, synthèse et analyse structurale de nouvelles molécules hôtes : Macrocycles et cyclophanes." Rouen, 2006. http://www.theses.fr/2006ROUES034.

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Dans la première partie, nous avons réalisé la synthèse de nouveaux composés dispiro-1. 3- dioxaniques sous forme d’isomères syn et anti. La synthèse de nouveaux macrocycles à motif 1. 3-dioxanique a été réalisée par la technique de la haute dilution et par effet template. La conception de ces macrocycles a été basée sur la connaissance de la stéréochimie des précurseurs et sur la pré-organisation de ces derniers, favorable à la formation des macrocycles. Dans la deuxième partie, nous avons réalisé la synthèse et l’analyse structurale de nouveaux dérivés dioxaniques du 1. 3. 5- triacétylbenzène et tenté la synthèse de nouvelles molécules « cages » à partir de ces dérivés
In the first part, we reported the synthesis of new dispiro-1. 3-dioxane compounds as syn and anti isomers. The synthesis of new macromolecules embedding semiflexible dispiro-1. 3-dioxane units was performed by high-dilution technique and using the template effect. The design of these macrocyclic compounds is based on the stereochemistry of the precursors which show a favourable pre-organization for the incorporation in macrocycle systems. In the second part, we reported the synthesis and the stereochemistry of new 1. 3. 5-triacetylbenzene derivatives and the attempts to obtain new “cage” molecules from these derivatives

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Cristau, Pierre. "Synthèses totales des mauritines A, B, C et F ; synthèse de macrocycles orientée pour la diversité structurale : conception et synthèse d'un cyclophane support d'un coude β." Paris 11, 2003. http://www.theses.fr/2003PA112184.

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Dans la première partie de ce manuscrit, nous avons decrit la première synthèse totale des mauritines a, b, c et f, alcaloi͏̈des cyclopeptidiques à 14 chaînons biologiquement actifs. La stratégie de synthèse que nous avons développé est basée sur une cycloétherification par réaction de s(n)ar intramoléculaire et met en jeu un tripeptide linéaire intact, ce qui rend la stratégie très convergente. Le rendement global de ces synthèses totales est de 6. 7-10. 2 pour cent pour 13-14 étapes. Une étude complète par spectroscopie rmn a été réalisée sur les mauritines a, b, c et f, permettant notamment d'attribuer, pour la première fois, tous les signaux correspondant aux protons mais aussi à tous les carbones. Dans la deuxième et troisième partie de ce manuscrit, nous avons décrit une nouvelle séquence ugi-s(n)ar permettant de synthétiser efficacement des macrocycles, analogues de produits naturels biologiquement actifs, qui comportent soit un motif biaryl éther soit un motif aryl-x-alkyl endocyclique (x = nh, 0, s). Cette séquence permet d'introduire une grande diversité structurale dans les molécules cibles et des macrocycles à 14, 15, 16 et 17 chaînons ont pu être synthétisés. Enfin, la séquence ugi-s(n)ar permettant d'accéder aux macrocycles comportant un motif biaryl éther a pu être appliquée aussi efficacement sur support solide (résine de wang). Dans la dernière partie de ce manuscrit, nous avons conÇu et synthétisé un nouveau cyclophane de type cycloisodityrosine, support externe potentiel d'un coude béta. Ainsi, quatre molécules cibles ont été synthétisées puis entièrement caractérisées. Une analyse conformationnelle détaillée (rmn, dichroi͏̈sme circulaire) a montré que cette unité cycloisodityrosine constitue vraisemblablement un bon support externe d'un coude béta du type ii, qui pourrait permettre le développement d'une nouvelle classe de peptidomimetiques
In the first part of this manuscript, we have detailled the first total syntheses of mauritines a, b, c and f, 14-membered cyclopeptide alkaloids with biological activity. Our strategy is very convergent and is based on the intramolecular s(n)ar cycloetherification which involves an intact linear tripeptide. The overall yield of these total syntheses is 6. 7-10. 2 per cent for 13-14 steps. For the first time detailled nmr studies allowed all proton and carbon signals to be attributed. In the second and third part of this manuscript, we have detailled a new ugi-s(n)ar sequence which allow the easy access to natural product-like macrocycles containing either an endocyclic biaryl ether or an aryl-x-alkyl pattern (x = nh, o, s). This sequence allow the introduction of broad structural diversity into the targetted molecules and 14 to 17-membered macrocycles have been synthesized. A solid supported version of this sequence was also developped for the synthesis of biaryl ether containing macrocycles (wang resin). In the last part of this manuscript, we have designed and synthesized a new macrocyclic beta turn scaffold. Thus four cycloisodityrosine-like macrocycles have been synthesized and fully characterized. A detailled conformational study (nmr, circular dichroi͏̈sm) showed that these targetted molecules are probably type ii beta turns. Therefore this new scaffold could be further considered for the developpment of a new class of peptidomimetics

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Renko, Zafiarisoa Dolor. "Synthèse totale de porphyrines protégées sur leurs deux faces (Porphyrines "Gyroscopes")." Paris 6, 1986. http://www.theses.fr/1986PA066274.

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La synthèse d'une nouvelle génération de porphyrines protégées sur leurs deux faces a été réalisée. Il s'agit d'un dérivé d'une octamethylporphyrine substituée en ses positions méso alpha et gamma par deux groupes phényles eux-mêmes fonctionnalises en position ortho et ortho par des anses peptidiques d'acides aminés optiquement actifs. L'une des anses comporte une pyridine. La synthèse totale de cette porphyrine a été effectuée en vue d'obtenir de nouveaux modèles d'hémoprotéines et de nouveaux catalyseurs d'époxydation asymétrique.

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Zahidi, Assou. "Etudes structurales et dynamiques de complexes macrocycliques par rmn heteronucleaire." Université Louis Pasteur (Strasbourg) (1971-2008), 1986. http://www.theses.fr/1986STR13171.

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Etude de la complexation de cations et d'anions par des ligands synthetiques a l'aide de la rmn heteronucleaire (**(6)li, **(7)li, **(13)c, **(14)n, **(15)n, **(19)f, **(31)p, **(35)cl et **(109)ag) et de mesures d'effet overhauser homo- et heteronuclaires

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Binay, Patrice. "Nouveaux modèles du NADH : réactivité et énantiosélectivité." Rouen, 1986. http://www.theses.fr/1986ROUES001.

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Dans une première partie, synthèse d'alkyl-4 dihydro-1,4 benzyl-1 et -phényl-1p éthyl-1 (diméthyl-4,4 oxazoline-2yl-2)-3 pyridines et étude de leur activité réductrice vis-a-vis de p-nitrobenzaldéhyde et de benzenéglyoxylate de méthyle en présence de mg**(2+) ; dans la seconde partie, étude de modèles plus énantiosélectifs : méthyl-1 dihydro-1,4 n-(hydroxyméthyl-1 propyl) nicotinamide (=méthyl-1 a), o-, m- et p- xylylene-1, 1' bis-a, dihydro-1,4 methyl-1 nicotinate de (dihydro-1,4 methyl-1 nicotinoylamino)-2 butyle et le cyclophane correspondant à ce dernier composé (pont xylylene entre les azotes des pyridines) ; interaction entre les noyaux pyridines

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"Synthesis of [beta]-ketomacrolides via 1-oxa[n]meta-cyclophanes and a new route to (+-)-patulolide C." Chinese University of Hong Kong, 1994. http://library.cuhk.edu.hk/record=b5895379.

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by Fong Sun.
On t.p., "+" appears over "-".
Thesis (M.Phil.)--Chinese University of Hong Kong, 1994.
Includes bibliographical references (leaves 41-43).
Acknowledgements --- p.i
Contents --- p.ii
Abstract --- p.iii
Abbreviations --- p.iv
Chapter I --- Introduction
Chapter I-1 --- General background --- p.1
Chapter I-2 --- Literature survey --- p.3
Chapter I-2-1 --- Ley's approach to β-ketomacrolides --- p.3
Chapter I-2-2 --- Weiler's approach to β-ketomacrolides --- p.4
Chapter I-2-3 --- Macrocyclic β-ketomacrolides formation through sulfide contraction ´ؤIreland's approach --- p.5
Chapter II --- Result and Discussion
Chapter II-1 --- General strategy for the synthesis of 1 -oxa[n]metacyclophanes --- p.7
Chapter II-2 --- l-Oxa[n]metacyclophanes as masked β-ketomacrolides synthons --- p.9
Chapter II-3 --- Application to the synthesis of natural products --- p.10
Chapter II-4 --- An alternate approach for the synthesis of (2E)-2-dodecen-l 1-olide´ؤA structural proof --- p.15
Chapter III --- Conclusion --- p.17
Chapter IV --- Experimental --- p.18
Chapter V --- References --- p.41
Chapter VI --- Spectra --- p.44

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Raymond, Michaël. "Synthèse de macrocycles par réaction de métathèse et application en débit continu." Thèse, 2016. http://hdl.handle.net/1866/18438.

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La réaction de macrocyclisation par métathèse est une réaction clé en synthèse organique et qui comporte de nombreux défis. Les méthodes traditionnelles de macrocyclisation impliquent par exemple la haute dilution du mélange réactionnel et l’emploie d’une pompe seringue. Dans cette thèse de doctorat, une méthode qui évite l’emploi des techniques de haute dilution a été développée. Cette méthode a été appliquée à la synthèse de cyclophanes macrocycliques. De plus, la synthèse totale de la néomarchantine A, un macrocycle bisbibenzylique, a été réalisée en 12 étapes à partir de produits commercialement disponibles avec un couplage d’Ullmann, un couplage de Wittig et une macrocyclisation par métathèse comme réactions clés. La chimie en débit continu, une méthode facilement applicable en milieu industriel, a été explorée. Cette technologie a été appliquée à l’étape clé de macrocyclisation par métathèse pour la synthèse de la néomarchantine A ainsi que pour la synthèse d’un musc macrocyclique breveté par la compagnie « International Flavors and Fragrances (IFF) ».
The macrocyclic metathesis reaction is a key reaction in organic synthesis and possesses numerous challenges. Traditional methods typically involve high dilution conditions and the use of a syringe pump. In this doctoral thesis, a method that avoids the use of dilution technics has been developed. This method has been applied to the synthesis of macrocyclic cyclophanes. Furthermore, total synthesis of neomarchantin A, a bisbibenzyl macrocycle, has been done in 12 steps from commercially available reagents with an Ullmann coupling, a Wittig coupling and a macrocyclic metathesis reaction as key steps. Continuous flow chemistry, a method easily applicable in an industrial setting, has been explored. This technology was applied to the key macrocyclization step of the neomarchantin A and for the synthesis of a macrocyclic musk patented by International Flavors and Fragrances (IFF).

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Books on the topic "Macrocyclic cyclophanes"

Weber, E. Topics in Current Chemistry: Macrocycles (Topics in Current Chemistry). Springer-Verlag Berlin and Heidelberg GmbH & Co. KG, 1991.

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Book chapters on the topic "Macrocyclic cyclophanes"

Campbell, Katie, and Rik R. Tykwinski. "Chiral Carbon-rich Macrocycles and Cyclophanes." In Carbon-Rich Compounds, 229–94. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2006. http://dx.doi.org/10.1002/3527607994.ch6.

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Li, Hao, Tianyu Jiao, and Libo Shen. "Host-Guest Chemistry of a Tetracationic Cyclophane, Namely, Cyclobis (paraquat-p-phenylene)." In Handbook of Macrocyclic Supramolecular Assembly, 1–33. Singapore: Springer Singapore, 2019. http://dx.doi.org/10.1007/978-981-13-1744-6_4-1.

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Li, Hao, Tianyu Jiao, and Libo Shen. "Host-Guest Chemistry of a Tetracationic Cyclophane, Namely, Cyclobis (paraquat-p-phenylene)." In Handbook of Macrocyclic Supramolecular Assembly, 49–81. Singapore: Springer Singapore, 2020. http://dx.doi.org/10.1007/978-981-15-2686-2_4.

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"Cyclophanes." In Macrocycles, 16–33. Chichester, UK: John Wiley & Sons, Ltd, 2011. http://dx.doi.org/10.1002/9780470980200.ch2.

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