Carbohydrate recognition of symmetrical tripodal receptor type tris(2-aminoethyl)amine derivatives

Mibu, Nobuko; Aki, Hatsumi; Ikeda, Hirohito; Saito, Ai; Uchida, Wataru; Yokomizo, Kazumi; Zhou, Jian-Rong; Miyata, Takeshi; Sumoto, Kunihiro

doi:10.1007/s10973-012-2813-5

Cited by 21 publications

(18 citation statements)

References 10 publications

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“…Therefore, for the purpose of preparation of designed alkoxy-amino-TAZ derivatives as our target molecules, the synthetic procedure via alkoxy-substituted chloro-TAZ is expected to be superior to the procedure via amine-substituted chloro-TAZs. Chart 2 shows the strategic point of synthetic pathways via alkoxy-chloro-TAZ derivatives (7,8) to alkoxy-amino-TAZ derivatives (3,4). Our method via alkoxy-substituted chloro-TAZ intermediates for target alkoxy-amino-TAZs consisting of stepwise nucleophilic substitutions gave moderate to excellent results as shown in Table 2.…”

Section: Resultsmentioning

confidence: 95%

“…Considering the nature of an introduced substituent characterizing the lipophilicity of a molecule, further modifications for finding more promising antiviral leads with better selectivity indexes are now under investigation. Based on the results of our previous studies on a few types of symmetrical compounds, [3][4][5] we speculate that a symmetrical molecule constructed on a symmetric template or with a linker may be an efficient structural feature. For the elucidation of sugar recognition properties of some of the highly bioactive symmetrical compounds such as 3ds, 3dt, 3is, and 4dss described in this article, we are also planning to carry out calorimetric experiments.…”

Section: Resultsmentioning

confidence: 99%

“…[3][4][5] With reference to the molecular symmetry, small molecules having C 3 -, C S -, or C 2 -symmetrical geometry frequently appear in various biologically active compounds. [6][7][8] Such small symmetrical molecules are usually constructed on a corresponding symmetrical template.…”

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confidence: 99%

“…3) We have also reported an interesting lectin-like property for sugar recognition of some of these tripodal receptor type TAEA molecules. 4) In order to achieve a suprafacial three-dimensional interaction of a bioactive symmetrical molecule for its binding site, the nature of substituents in the molecule is thought to be very important for preferential interactions. Such interactions are dictated largely by van der Waals interactions or formation of hydrogen bonds.…”

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Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

et al. 2013

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We describe the synthesis and biological evaluation of newly designed 2,4,6-trisubstituted symmetrical 1,3,5-triazine (TAZ) derivatives. Among the tested trisubstituted symmetrical TAZ derivatives, various C 3 -or C S -symmetrical alkoxy-amino-substituted TAZ derivatives showed significant antiviral activity against herpes simplex virus type 1 (HSV-1) and/or cytotoxic activity against Vero cells. The structure-activity relationships for anti-HSV-1 activity of these symmetrical 2,4,6-trisubstituted TAZ derivatives are also described. Experimental results indicated that a C S -symmetrical TAZ structure with introduction of two alkoxy groups and one amine moiety seems to be the minimally required structure for anti-HSV-1 activity.Key words 1,3,5-triazine; anti-herpes simplex virus type 1; cytotoxic activity; C 3 symmetry; C S symmetry; plaque reduction assay Molecular recognition of two-fold (C 2 ) or three-fold (C 3 ) symmetrical geometry macromolecules is one of the common features in many important biological responses, 1,2) and we have therefore already designed a few symmetrical target molecules for the purpose of finding biologically active new leads or candidates.3-5) With reference to the molecular symmetry, small molecules having C 3 -, C S -, or C 2 -symmetrical geometry frequently appear in various biologically active compounds. [6][7][8] Such small symmetrical molecules are usually constructed on a corresponding symmetrical template.From this point of view, we have recently reported some molecular modifications of tris(2-aminoethyl) amine (TAEA) derivatives to C 3 -or C S -symmetrical tripodal receptor type molecules and the results of biological evaluation of these symmetrical compounds.3) We have also reported an interesting lectin-like property for sugar recognition of some of these tripodal receptor type TAEA molecules. 4)In order to achieve a suprafacial three-dimensional interaction of a bioactive symmetrical molecule for its binding site, the nature of substituents in the molecule is thought to be very important for preferential interactions. Such interactions are dictated largely by van der Waals interactions or formation of hydrogen bonds. The introduction of amine (basic nitrogen atom) and/or a bivalent oxygen group such as a hydroxy or alkoxy group into a C 3 -symmetrical 1,3,5-triazine (TAZ) template seems to be interesting, because it is well known that amine functionalities behave as both hydrogen acceptors and hydrogen donors in appropriate circumstances. These facts may indicate that molecules with some amine and/or bivalent oxygen functionalities on a heterocyclic C 3 -symmetrical TAZ template can produce a property for suprafacial hydrogenbonding interaction.For an extension of our studies, we planned to investigate the synthesis of 2,4,6-trisubstituted symmetrical TAZ derivatives [9][10][11][12][13][14][15][16] as well as to evaluate their biological properties. In this paper, we report the results of new synthetic routes for C 3 -or C S -symmetrical 2,4,6-trisubstituted TAZ derivativ...

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confidence: 95%

Section: Resultsmentioning

confidence: 99%

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Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

et al. 2013

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“…5 We have been interested in small molecules that interfere with such carbohydrate recognition stages in order to find new bioactive leads. [6][7][8] Regarding carbohydrate (sugar chain) recognition molecules, we have been particularly interested in boronic acid derivatives because many boronic acid functionalities (A) have a property to react with various 1,2-diol functionalities included in carbohydrates and generate cyclic derivatives (B) formed with reversible covalent bonds (see Figure 1). 9,10 From this point of view, we have recently synthesized a few …”

Section: Novel Trivalentmentioning

confidence: 99%

Novel Trivalent C3-Symmetrical Phenylboronic Acid Pinacol Esters and Their Biological Evaluation

Sumoto¹,

Furutachi²,

Fuchigami³

et al. 2018

HETEROCYCLES

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-We report the preparation of newly designed trivalent C 3 -symmetrical cyclic phenylboronic acid derivatives constructed on a symmetrical benzene or a cyclohexane ring. The synthesis of these C 3 -symmetrical molecules 4 was accomplished by an amide bond formation reaction using amino-substituted phenylboronic acid pinacol esters 2 and C 3 -symmetrical benzene-1,3,5-tricarboxylic acid trichloride 3a or cyclohexane-1,3,5-tricarboxylic acid trichloride 3b in the presence of Et 3 N. We confirmed that this procedure is conventionally applicable to the preparation of targeted C 3 -symmetrical cyclic boronic acid derivatives 4 in good to excellent yields. We also report the results of biological evaluation of the prepared compounds.Many host receptors that consist of homo-oligometric units (homo-multiligands) often construct symmetric macromolecule architectures such as C 2 -or C 3 -symmetrical geometry receptor systems.Molecular recognition of two-fold (C 2 ) or three-fold (C 3 ) geometric symmetrical macromolecules is one of the common features in several important biological processes. 1,2 With reference to the molecular symmetry, small oligovalent molecules having C 2 -or C 3 -symmetrical geometry have frequently appeared in various biologically active substances. [2][3][4] An oligovalent molecule is generally expected to show enhanced biological potential compared to that of the corresponding monovalent molecule. 4 On the other hand, regarding lectin-like carbohydrate recognition molecules, much attention has recently been paid to the design of synthetic receptors for carbohydrates. 5 We have been interested in small molecules that Figure 1). 9,10 From this point of view, we have recently synthesized a few 11 Figure 1As an extension of this study, we carried out further investigations of these symmetrical classes of compounds. In this paper, we report the synthesis of new trivalent C 3 -symmetrical phenylboronic acid derivatives incorporating a benzene or cyclohexane ring as a symmetrical template in the molecules and we report results of biological evaluations of the obtained C 3 -symmetrical phenylboronic acid derivatives.The results for synthesis of new C 3 -symmetrical cyclic boronic acid derivatives constructed on a benzene ring or a cyclohexane ring having three amide bonds are summarized in Tables 1 and 2. The synthesis of these target trivalent C 3 -symmetrical molecules 4aa~4ca constructed on a benzene ring was accomplished by an amide bond formation reaction using amino-substituted phenylboronic acid pinacol esters 2 and benzene-1,3,5-tricarboxylic acid trichloride 3a in the presence of a base such as Et 3 N. The preparation and physical and spectroscopic data of compounds 4aa~4ca have been reported in detail as a separated paper. 13 New C 3 -symmetrical compounds 4ab and 4bb constructed on a cyclohexane ring were also prepared by a procedure similar to that for compounds 4aa~4ca with cyclohexane-1,3,5-tricarboxylic acid trichloride in good yields (see EXPERIMENTAL). The structures of targe...

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Carbohydrate recognition of C3-symmetrical tripodal receptor-type 2,4,6-trisubstituted 1,3,5-triazine derivatives with antiviral activities

Mibu

Ohata

Sano

et al. 2018

J Therm Anal Calorim

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Carbohydrate recognition of symmetrical tripodal receptor type tris(2-aminoethyl)amine derivatives

Cited by 21 publications

References 10 publications

Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

Novel Trivalent C3-Symmetrical Phenylboronic Acid Pinacol Esters and Their Biological Evaluation

Carbohydrate recognition of C3-symmetrical tripodal receptor-type 2,4,6-trisubstituted 1,3,5-triazine derivatives with antiviral activities

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