Can C3‐Symmetric Receptors Differentiate Enantiomers?

Moberg, Christina

doi:10.1002/anie.200601214

Cited by 81 publications

(23 citation statements)

References 14 publications

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“…Applications of C 3 -symmetrical functional receptor molecules in the area of molecular recognition have led to significant advances, and it is also expected that the use of C 3 -symmetrical molecules will lead to many developments in molecular recognition stages. 27) Regarding carbohydrate recognition by C 3 -type symmetrical small molecules, we consider that the results obtained for diastereo-selective sugar recognition in some monosaccharides such as MeO-α/β-Gal by compound 4e may provide useful information for research on carbohydrates recognition, especially by an achiral small molecule with three-fold (C 3 -geometrical) symmetry. 28) On the basis of this information on sugar recognition of C 3 -symmetrical antiviral active TAZ derivative 4e, we are also planning to carry out further molecular modifications to the related trisubstituted TAZ derivatives with branched C3-C5 alkoxy groups similar to the isopropoxy group.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antiviral Evaluation of Some C3-Symmetrical Trialkoxy-Substituted 1,3,5-Triazines and Their Molecular Geometry

et al. 2015

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As one of our projects, we here report some new molecular modifications of 2,4,6-trichloro-1,3,5-triazine (TCTAZ: 1) to symmetrical 2,4,6-trialkoxy-or 2,4,6-triaryloxy-substituted 1,3,5-triazine (TAZ) molecules, as well as the results of anti-herpes simplex virus type 1 (anti-HSV-1) activity evaluation of synthesized 2,4,6-trisubstituted TAZ derivatives. Among the tested 2,4,6-trisubstituted TAZ derivatives, we reconfirmed that a C 3 -symmetrical TAZ derivative, 4e, shows the highest level of anti-HSV-1 activity with a good selectivity index. In this paper, we also report the results of the preparation of newly targeted TAZ derivatives and the structure-activity relationships (SARs) of these trialkoxy-substituted TAZ derivatives and related compounds. The sugar recognition properties of C 3 -symmetrical TAZ derivative 4e are also described.Key words 1,3,5-triazine; C 3 symmetry; anti-herpes simplex virus type 1; structure-activity relationship; plaque reduction assay; isothermal titration calorimetryThe glycocalyx at the cell surface, containing glycoproteins, proteoglycans and glicolipids, plays an important role in various cell-to-cell communications. Specific interactions of these carbohydrates with lectins (protein receptors) are important biological processes, including the processes of bacterial or viral infection and tumor metastasis. 1-3)From the viewpoint of molecular symmetry, many host receptors that consist of homo-oligometric units (homomultiligands) often construct symmetric macromolecule architectures such as C 2 -or C 3 -symmetrical geometry receptor systems. These phenomena of macromolecules connected with many biological stages have encouraged scientists to develop new multivalent symmetrical synthetic molecules to find new bioactive compounds or leads. Results of many works related to the above conception have been published over the past few decades. [4][5][6][7] The terms identical twin-drugs and tripletdrugs (symmetrical bivalent and trivalent molecules) are now commonly used in medicinal chemistry and related scientific fields. In connection with our synthetic works on such symmetrical molecules, we have already designed and synthesized a few new symmetrical molecules and evaluated their bioactivities in order to find new types of bioactive compounds. 8-17)In connection with the above projects, we have recently reported some molecular modifications of 2,4,6-trichloro-1,3,5-triazine (TCT AZ) (1) to symmetrical 2,4,6-trisubstituted 1,3,5-triazine (TAZ) molecules and the results of biological evaluation of synthesized symmetrical 2,4,6-trisubstituted TAZ derivatives. 8,9) Among previously targeted trisubstituted TAZ derivatives, we found that a C 3 -symmetrical TAZ derivative with three isopropoxy groups on a TAZ template such as compound 4e showed a high level of anti-herpes simplex virus (HSV)-1 activity and low cytotoxity, and it therefore seemed to be a potential lead in the search for preferred anti-HSV-1 activity with a good selectivity index (SI).In this paper, we report the results of...

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Section: Resultsmentioning

confidence: 99%

Synthesis and Antiviral Evaluation of Some C3-Symmetrical Trialkoxy-Substituted 1,3,5-Triazines and Their Molecular Geometry

et al. 2015

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“…[14] The C 2 -symmetric macrocycle 2 shows a selectivity ratio in acetonitrile of 3.65 for the perchlorate salt of (R)-α-(1-naphthyl)ethylamine (K a = 7753  -1 ) vs. the perchlorate salt of (S)-α-(1-naphthyl)-ethylamine (K a = 2123  -1 ). [15] The question of whether or not C 3 -or D 3 -symmetric systems are able to act as receptors for chiral recognition has been controversial for a long time, [18] and Ahn et al were the first to succeed in synthesizing a C 3 -symmetric receptor (3), which shows selectivity ratios of up to 71:29 in chloroform in the field of enantiomeric discrimination. [17] This receptor type is built by coupling the chiral binding arms to the achiral backbone in such a way that they can organize themselves around a potential guest in a predetermined ar-rangement.…”

Section: Introductionmentioning

confidence: 99%

“…[10] Presently, crown ether derivatives showing C 1 or C 2 symmetry prevail as receptors for primary organoammonium salts, [13][14][15] and there are only a few examples of enantioselective receptors for chiral ammonium ions with C 3 symmetry. [16,17] A recent example of a C 1 -symmetric receptor is the macrocycle 1, which provides in chloroform a selectivity ratio of 2.50 for the perchlorate salt of (R)-α-phenylethylamine (K a = 33000  -1 ) vs. the perchlorate salt of (S)-α-phenylethyl- The question of whether or not C 3 -or D 3 -symmetric systems are able to act as receptors for chiral recognition has been controversial for a long time, [18] and Ahn et al were the first to succeed in synthesizing a C 3 -symmetric receptor (3), which shows selectivity ratios of up to 71:29 in chloroform in the field of enantiomeric discrimination. [17] This receptor type is built by coupling the chiral binding arms to the achiral backbone in such a way that they can organize themselves around a potential guest in a predetermined ar-rangement.…”

Section: Introductionmentioning

confidence: 99%

Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by C₃‐Symmetric Peptide Receptors

Schnopp

Haberhauer

2009

Eur J Org Chem

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A straightforward synthesis of C3‐symmetric, imidazole‐containing, macrocyclic peptides with different binding arms is presented. The chirality of the backbone and the selection of adequate receptor arms make these systems highly selective receptors for α‐chiral primary organoammonium ions. Furthermore, the receptors have the ability to discriminate between enantiomeric guests with selectivity ratios of up to 87:13. The binding constants and the selectivity ratios were estimated by standard 1H NMR titration techniques in CDCl3. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…[1] Examples are C 3 symmetric platforms, [2][3][4][5][6] which stem from Lissoclinum cyclopeptide alkaloids. [1] Examples are C 3 symmetric platforms, [2][3][4][5][6] which stem from Lissoclinum cyclopeptide alkaloids.…”

Section: Introductionmentioning

confidence: 99%

N‐Aryl Imidazole Platforms – Synthesis and Structural Investigation

et al. 2018

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Cyclic oligomers of azole peptides were isolated from a multitude of marine organisms and were used for a variety of applications in supramolecular chemistry. Up to now the use of imidazole‐containing platforms based on Lissoclinum cyclopeptides were limited to N‐alkyl imidazole scaffolds. Here we present the synthesis of chiral N‐aryl imidazole amino acids by starting from the corresponding amidoketones and aniline derivatives. By using the optimized reaction conditions even chiral imidazoles with large substituents at the α‐carbon atom and at ortho position of the aryl ring were obtained without racemization at the stereogenic center. Subsequent one‐pot cyclotrimerization of the N‐aryl imidazole amino acids leads to the desired C3‐symmetric platforms in rather good yields. The investigation of the structures of the platforms with bromine atoms in ortho, meta and para position relative to the imidazole unit were conducted by NMR spectroscopy, X‐ray crystallography, and quantum chemical calculations. The experimental data reveals that the ortho isomer is present in a single conformer in which all bromine atoms are oriented in the same direction. The rotation around the aryl‐imidazole axis in this isomer is completely prevented in the measured temperature range.

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Can C₃‐Symmetric Receptors Differentiate Enantiomers?

Cited by 81 publications

References 14 publications

Synthesis and Antiviral Evaluation of Some <i>C</i><sub>3</sub>-Symmetrical Trialkoxy-Substituted 1,3,5-Triazines and Their Molecular Geometry

Synthesis and Antiviral Evaluation of Some <i>C</i><sub>3</sub>-Symmetrical Trialkoxy-Substituted 1,3,5-Triazines and Their Molecular Geometry

Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by C₃‐Symmetric Peptide Receptors

N‐Aryl Imidazole Platforms – Synthesis and Structural Investigation

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Can C3‐Symmetric Receptors Differentiate Enantiomers?

Cited by 81 publications

References 14 publications

Synthesis and Antiviral Evaluation of Some <i>C</i><sub>3</sub>-Symmetrical Trialkoxy-Substituted 1,3,5-Triazines and Their Molecular Geometry

Synthesis and Antiviral Evaluation of Some <i>C</i><sub>3</sub>-Symmetrical Trialkoxy-Substituted 1,3,5-Triazines and Their Molecular Geometry

Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by C3‐Symmetric Peptide Receptors

N‐Aryl Imidazole Platforms – Synthesis and Structural Investigation

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Can C₃‐Symmetric Receptors Differentiate Enantiomers?

Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by C₃‐Symmetric Peptide Receptors