Search results
Search for "macrocyclic" in Full Text gives 268 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Nanopatterns of arylene–alkynylene squares on graphite: self-sorting and intercalation
Beilstein J. Org. Chem. 2019, 15, 1848–1855, doi:10.3762/bjoc.15.180
- the procedure described above) a nanopattern of 1a (5 × 10−7 M), and added a 10−4 M solution of 3 in TCB. STM (Figure 4a) shows – again – bright features in the macrocyclic template of 1a. Again, a slight central depression is visible in the STM image which can attributed to the empty center region of
- images comprising both polymorphs are shown in Supporting Information File 1, Figure S9a and b. Therefore, the PAH coadsorption is a monitor for the alkoxy chain orientation inside the macrocyclic interior (whereas they do not point towards the solution phase here). By adding a solution of 3 at a
Novel macrocycles – and old ones doing new tricks
Beilstein J. Org. Chem. 2019, 15, 1838–1839, doi:10.3762/bjoc.15.178
- special issue in the Beilstein Journal of Organic Chemistry gathers world-renowned experts in the field to share their very recent results and will surely help stimulate macrocyclic chemistry. Wei Jiang and Christoph A. Schalley Shenzhen, Berlin, July 2019
Synthesis of a [6]rotaxane with singly threaded γ-cyclodextrins as a single stereoisomer
Beilstein J. Org. Chem. 2019, 15, 1829–1837, doi:10.3762/bjoc.15.177
- Jason Yin Hei Man Ho Yu Au-Yeung Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China 10.3762/bjoc.15.177 Abstract A series of hetero [4]-, [5]- and [6]rotaxanes containing both cucurbit[6]uril (CB[6]) and γ-cyclodextrin (γ-CD) as the macrocyclic components
- interested in exploiting the binding capability of γ-CD in the construction of high order [n]rotaxanes and [n]catenanes. Here, we report our work on the synthesis of multiring, hetero[n]rotaxane containing γ-CD and cucurbit[6]uril (CB[6]) as the macrocyclic components in an aqueous medium. Because of the
Complexation of 2,6-helic[6]arene and its derivatives with 1,1′-dimethyl-4,4′-bipyridinium salts and protonated 4,4'-bipyridinium salts: an acid–base controllable complexation
Beilstein J. Org. Chem. 2019, 15, 1795–1804, doi:10.3762/bjoc.15.173
- ; macrocycles; macrocyclic arene; Introduction Macrocyclic host molecules [1][2] play a significant role in host–guest chemistry. Compared with noncyclic molecules, the structures of macrocyclic hosts can greatly enhance the host–guest complexation ability through preorganization. Moreover, cyclic structures
- are also the epitome of complex-binding pockets of enzymes [3]. Macrocyclic arenes including calixarenes [4][5], resorcinarenes [6], cyclotriveratrylenes [7][8], pillararenes [9], biphen[n]arenes [10] and others [11][12] are all composed of hydroxy-substituted aromatic rings bridged by methylene or
- methenyl groups. They have been a kind of important macrocyclic host molecules during the last decades due to their unique structures and a wide range of applications in host–guest chemistry [13][14][15][16][17][18], self-assembly [19], biomedicine [20] and materials science [21][22]. The derivatives of
Host–guest interactions in nor-seco-cucurbit[10]uril: novel guest-dependent molecular recognition and stereoisomerism
Beilstein J. Org. Chem. 2019, 15, 1705–1711, doi:10.3762/bjoc.15.166
- Xiaodong Zhang Wei Wu Zhu Tao Xin-Long Ni Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China 10.3762/bjoc.15.166 Abstract The unique monomer and excimer fluorescence emissions of pyrene were first exploited as distinctly
- because of their varying cavity rigidity and larger portal sizes as compared with those of other macrocyclic hosts [4][5][6][7][8][9][10][11][12][13]. For example, cucurbit[8]uril (Q[8] or CB[8]), a large homologue of the Q[n] family, is unique because of its ability to bind two hetero- and homo-aromatic
Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments
Beilstein J. Org. Chem. 2019, 15, 1601–1611, doi:10.3762/bjoc.15.164
- guest receptors [4][5]. Planar-chiral macrocyclic molecules are particularly interesting in the context of the host–guest complexation properties [6][7][8]. Pillararenes are typical examples of this type of compounds and have attracted considerable attention due to their facile chemical synthesis and
- quantum yield was significantly decreased to 46.4% compared with 78.2% for Py-6. We ascribed the decreased fluorescence of P5A-Py to the π–π stacking of the Py units caused by the high local concentration of perylene. For P5A-DPA, which also bears two DPA units in one macrocyclic host, the fluorescent
- assigned to the excimer emission of Py (Figure S23, Supporting Information File 1) [54]. Conclusion Two new planar chiral macrocyclic hosts P5A-DPA and P5A-Py were synthesized by grafting two fluorophore pigments (DPA or Py) on pillar[5]arene through CuAAC “click” reaction. The new macrocyclic compounds
An azobenzene container showing a definite folding – synthesis and structural investigation
Beilstein J. Org. Chem. 2019, 15, 1534–1544, doi:10.3762/bjoc.15.156
- chemistry. Here, we present the synthesis of a foldable container consisting of two different types of Lissoclinum macrocyclic peptides which are connected via two azobenzene units. The container is controllable by light: irradiation with UV light causes a switching process to the compact cis,cis-isomer
- are determined by the type and size of the macrocyclic platform, e.g., if all of the amino acid side chains are of the same configuration, they are presented on one face of the macrocycle in a convergent manner. The artificial Lissoclinum cyclopeptide platforms feature C2, C3 and C4 symmetry [3]. So
- -isomer (Figure 8). Conclusion In conclusion, we were able to synthesize a foldable container consisting of two different types of Lissoclinum macrocyclic peptides which are connected via two azobenzene units. The synthesis of this container was achieved by a one pot reaction of the two imidazole
2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes
Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146
- –guest chemistry; macrocycles; molecular recognition; precious metal chloride complexes; Introduction Macrocyclic receptors are the major workhorses in supramolecular chemistry. Design and synthesis of new macrocyclic receptors with new properties is always attractive but is also challenging [1
- interesting new binding properties. During the last six years, our group have developed a series of naphthol-based macrocyclic receptors [24][25][26][27][28][29]. Of them, oxatub[4]arene [30][31] and zorb[4]arene [32][33] show multiple conformations due to the flipping of naphthalenes and thus resulted in a
Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response
Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139
- binding of the analyte gives rise to an extraordinary luminescence response of the reporter dye. Macrocyclic hosts constitute a family of well-studied artificial receptors with a discrete cavity that is selective for complementary binding to certain guests [9]. Modulation of properties of organic
- fluorophores through supramolecular encapsulation using artificial macrocyclic hosts has always been an active research area [10][11][12]. The complexes of macrocycles with luminescent dyes not only act as reporter pairs for sensing [13][14][15], but also offer various applications in bioimaging [16][17
- supramolecular cavities [25]. Calixarenes are the third generation of macrocyclic compounds composed of phenolic units bridged with methylene groups at the o-positions of phenolic hydroxy groups [9]. We have focused on molecular recognition and self-assembly of water-soluble calixarene derivatives for a long
Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study
Beilstein J. Org. Chem. 2019, 15, 1321–1330, doi:10.3762/bjoc.15.131
- molecules [27], including some amino acids [28] and proteins [29]. They are also biocompatible: compared to other types of macrocyclic molecules such as cyclodextrins and cucurbiturils (which are also water soluble), p-sulfonatocalix[n]arenes do not exhibit any toxicity, which makes them applicable in
Bambusuril analogs based on alternating glycoluril and xylylene units
Beilstein J. Org. Chem. 2019, 15, 1268–1274, doi:10.3762/bjoc.15.124
- which can interact with cationic, anionic or neutral guest molecules. Here we present the design and synthesis of a new hybrid macrocycle containing glycoluril and aromatic units. The reaction afforded a mixture of macrocyclic homologues from which a two-membered macrocycle was isolated as the main
- urea groups can participate in intermolecular hydrogen bonding resulting in the formation of tubular [5][6][7] or gel-like [8] structures. Ureas lacking of N–H hydrogen atoms such as ethyleneureas, glycolurils, and biotin are also important building blocks of macrocyclic receptors such as cucurbiturils
- spectroscopy was not possible due to the low absorption of bambusurils within the UV–vis region. Therefore, we decided to investigate the synthesis of bambusuril derivatives and analogs containing chromophores in their structure. Initially we tested post-macrocyclic functionalization resulting in bambusurils
N-doped carbon dots covalently functionalized with pillar[5]arenes for Fe3+ sensing
Beilstein J. Org. Chem. 2019, 15, 1262–1267, doi:10.3762/bjoc.15.123
- macrocyclic compounds, especially new macrocyclic arenes, have become one of the research hotspots in supramolecular chemistry [11][12][13][14]. Among them pillarenes as a relatively new family of pillar-shaped members discovered a decade ago have played a key role due to their unique conformations
Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium
Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117
- macrocyclic hosts, crown ethers, have been widely used as building blocks for supramolecular assemblies in the past two decades [37][38][39][40][41][42][43][44][45][46][47][48][49][50][51][52][53], mainly in the fabrication of crown ether-based threaded or interlocked assemblies in organic solvents [54
- ]. However, we recently found that benzo-21-crown-7 (B21C7) displays impressive high water solubility in comparison with other macrocyclic hosts [55]. Moreover, the conjugation of B21C7s to the well-known supramolecular BTA core leads to the observation of special topological effects on ion selectivity in
Molecular recognition using tetralactam macrocycles with parallel aromatic sidewalls
Beilstein J. Org. Chem. 2019, 15, 1086–1095, doi:10.3762/bjoc.15.105
- aromatic sidewalls and four NH residues directed into the macrocyclic cavity. These macrocycles are versatile hosts for a large number of different guest structures in water and organic solvents, and they are well-suited for a range of supramolecular applications. The macrocyclic cavity contains a mixture
- selectivity. In organic solvents, the supramolecular factors are reversed; the polar NH groups drive high affinity and the aromatic surfaces provide the secondary interactions. In addition to an amphiphilic cavity, macrocyclic tetralactams exhibit conformational flexibility, and the combination of properties
- effect; macrocycles; rotaxane; supramolecular; Review 1. Introduction A large fraction of host–guest chemistry research uses macrocyclic compounds as the host molecules [1][2]. There are several reasons for this circumstance. Macrocycles are often relatively easy to synthesize and they have inherently
Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions
Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88
- diastereomers. After converting 68 into aldehyde 69, this was reacted with cyclopropyl isocyanide 57 and acetic acid (Passerini reaction) furnishing compound 70, which was converted to telaprevir (64) in three additional steps. Macrocyclic peptoid synthesis Dömling et al. performed the combination of two
- bifunctional compounds 74 at the end, allowing the obtention of the 16- to 20-membered tetrazolic macrocycles 75 in only five steps (Scheme 14). A similar approach was used shortly afterwards by the same research group in the synthesis of macrocyclic depsipeptides containing a tetrazole nucleus [31]. The
- combination of two isocyanide-based multicomponent reactions (azido-Ugi and Passerini reactions) allowed easy access to a library of macrocyclic depsipeptides in only four steps with variations in the size of the macrocycle as well as in the side chains (Scheme 15). This was the first example in which the
Mechanochemistry of supramolecules
Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86
- –acceptor [2]rotaxanes such as 19 through liquid-assisted mechanochemical milling (Figure 9). The donor–acceptor interaction between the electron-deficient naphthalene diimide moiety and the electron-rich naphthalene moieties embedded in the macrocyclic polyethers played the vital role for the construction
Coordination chemistry and photoswitching of dinuclear macrocyclic cadmium-, nickel-, and zinc complexes containing azobenzene carboxylato co-ligands
Beilstein J. Org. Chem. 2019, 15, 840–851, doi:10.3762/bjoc.15.81
- represents a 24-membered macrocyclic hexaaza-dithiophenolate ligand, L' is an azobenzene carboxylate co-ligand, and M = Cd(II), Ni(II) or Zn(II), is reported. A series of new complexes were synthesized, namely [M2L(μ-L')]+ (L' = azo-H, M = Cd (1), Ni (2); L' = azo-OH, M = Zn (3), Ni (4); L' = azo-NMe2, M
- with λ = 365 nm reveals a photoisomerization of the co-ligand from the trans to the cis form. Keywords: azobenzene carboxylates; cadmium; complexes; macrocyclic ligands; nickel; zinc; Introduction The macrocyclic N6S2 donor ligand H2L is an effective dinucleating ligand that supports a large number
- '. The co-ligand binds again via its carboxylato function in a μ1,3-bridging mode to give a Zn···Zn distance of 3.440 Å, which is typical for carboxylato-bridged Zn complexes supported by the macrocyclic N6S2 donor ligand. The average Zn–S, Zn–N and Zn–O distances are at 2.536 Å, 2.305 Å, and 2.049 Å
Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks
Beilstein J. Org. Chem. 2019, 15, 721–726, doi:10.3762/bjoc.15.67
- ], thioether macrocycles [11], macrocyclic Schiff bases [12] or even poly(phthalaldehyde) polymers [13]; taking into account that few studies were carried out with modified OPA on position 3 or 4. This could probably be due to the fact that the synthesis of 4-substituted OPA was, to the best of our knowledge
Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes
Beilstein J. Org. Chem. 2019, 15, 617–622, doi:10.3762/bjoc.15.57
- Krzysztof M. Zwolinski Julita Eilmes Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387 Kraków, Poland 10.3762/bjoc.15.57 Abstract The first crown ether-capped dibenzotetraaza[14]annulenes (DBTAAs), featuring two macrocyclic binding sites fixed in a face-to-face orientation
- ], little research has been undertaken regarding DBTAAs functionalized with crown ether moieties (see Figure 1). Kruse and Breitmaier [24] reported annulated DBTAA‘s containing benzo-15-crown-5 scaffolds fused with benzenoid rings of the macrocyclic core. Both nickel(II) and cobalt(II) complexes were
- showed cation and solvent-induced dimerisation. More recently, Raston et al. reported the synthesis of Goedken’s macrocycle tmtaa nickel(II) complex featuring a single oligo(ethylene glycol) chain strapped across the face of the DBTAA macrocyclic core [28]. However, to the best of our knowledge, there
Synthesis and SAR of the antistaphylococcal natural product nematophin from Xenorhabdus nematophila
Beilstein J. Org. Chem. 2019, 15, 535–541, doi:10.3762/bjoc.15.47
- moiety itself are required for bioactivity [16]. These findings suggest a specific interaction of this electrophilic moiety with a nucleophile. Such an interaction was previously reported for the macrocyclic peptide cyclotheonamide A, isolated from marine sponge Theonella sp. Cyclotheonamide A is
Selectivity in multiple multicomponent reactions: types and synthetic applications
Beilstein J. Org. Chem. 2019, 15, 521–534, doi:10.3762/bjoc.15.46
- interesting case, where this principle does not apply, is introduced by Wessjohann [5][18], who introduced a family of MMCRs leading to complex macrocyclic structures instead of linear polymer chains. In these examples, a low concentration together with the use of specific substrates tune the reactivity
- pattern, promoting intramolecular interactions over intermolecular polymerizations. Thus, the use of the right conditions and the intelligent choice of the polyfunctionalized building blocks, enable an “architectural approach” towards the MMCR synthesis of macrocyclic adducts [19]. This multiple
- [21], supramolecular structures (cryptands, cages, cryptophanes, podands, etc.) [22][23][24], cyclic/macrocyclic peptides [25] and other complex structures in a straightforward manner (Scheme 5). The diversity in these systems arises not only from combining a variety of building blocks (from simple
Design of indole- and MCR-based macrocycles as p53-MDM2 antagonists
Beilstein J. Org. Chem. 2019, 15, 513–520, doi:10.3762/bjoc.15.45
- ring. It is estimated that 3% of the known natural products consists of a macrocyclic ring [1][2][3][4][5]. Compared to macrocycles in synthetic molecules, the aforementioned occurrence is still over proportional; for that reason, these compounds have delighted scientists worldwide due to their special
- physicochemical properties, their roles in biological systems and the associated synthetic challenges [6][7]. However, only few synthetic methods allow for the convergent and fast access to a large macrocyclic chemical space [8][9][10]; most of the times their synthesis is complex, multistep and sequential [11
- MDM2–p53 interaction could enable p53 and reverse tumor formation [26][27][28]. Based on our knowledge to antagonize the oncogenic protein–protein interaction p53–MDM2 [23][29][30][31][32][33][34][35][36][37][38][39][40] we designed macrocyclic inhibitors in continuation of our previous work [13][23
Chemical structure of cichorinotoxin, a cyclic lipodepsipeptide that is produced by Pseudomonas cichorii and causes varnish spots on lettuce
Beilstein J. Org. Chem. 2019, 15, 299–309, doi:10.3762/bjoc.15.27
- treatment had no activity, supporting that a macrocyclic peptide would be essential for biological activity. The sequence Z-dhThr17-D-alloThr18 of cichorinotoxin was converted to Z-dhThr17-E-dhThr18 by alkaline hydrolysis. This additional structural modification may have further decreased the activity
Olefin metathesis in multiblock copolymer synthesis
Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21
- -substituted NB with poly(ethylene glycol) (PEG) [69]. Ring-opening metathesis copolymerization of the rather strained cyclooctene (COE) and a strainless 27-membered macrocyclic olefin (MCO) led to the multiblock copolymer consisting of octenylene blocks linked with ring-opened MCO segments (Scheme 6) [70
First synthesis of cryptands with sucrose scaffold
Beilstein J. Org. Chem. 2019, 15, 210–217, doi:10.3762/bjoc.15.20
- ’,4,4’-penta-O-benzylsucrose and 1’,2,3,3’,4,4’-hexa-O-benzylsucrose. Keywords: cryptands; macrocyclization; sucrose; Introduction The design and synthesis of macrocyclic receptors is one of the main challenges of supramolecular chemistry [1][2]. These artificial systems exhibit interesting properties
- ]. There are also reports on the preparation of ‘distorted’ cyclodextrins in which diverse fragments are incorporated into the original oligosaccharide ring(s) [5]. Another class of sugar receptors is represented by macrocyclic derivatives with the carbohydrate unit being a part of a crown or aza-crown
- sucrose scaffold (e.g., 4) can be also prepared successfully [15][16]. All macrocyclic derivatives, shown in Figure 1, were prepared from hexa-O-benzylsucrose 3 by a connection of the terminal positions of glucose (C6) and fructose (C6’) units. Results and Discussion Diol 3 may be also used as a starting
Other Beilstein-Institut Open Science Activities
