Triazole-oligomers by 1,3-dipolar cycloaddition

Katritzky, Alan R.; Singh, Sandeep K.; Meher, Nabin K.; Doskocz, Jacek; Suzuki, Kazuyuki; Jiang, Rong; Sommen, Geoffroy L.; Ciaramitaro, David A.; Steel, Peter J.

doi:10.3998/ark.5550190.0007.505

Cited by 35 publications

(13 citation statements)

References 8 publications

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“…The conformation of T3C 4 in the crystal exhibits two 1,2,3‐triazole rings pointing to the same direction and therefore is not C 3 ‐symmetric (Figure 2 a and Figure S1 in the Supporting Information). Although not usual, the non‐ C 3 ‐symmetric structure has also been found in star‐shaped triazines substituted with 1‐benzyl‐4‐(trimethylsilyl)‐1,2,3‐ triazol‐5‐yl [10] or 5‐(4‐propyloxyphenyl)‐1,3,4‐oxadiazol‐2‐yl [11] arms, and supports the non‐symmetric structure claimed for the self‐assembly of some polycatenar tris(triazolyl)triazines in the columnar mesophases and their polar nature [12] . The core of T3C 4 formed by the triazine and the triazole rings is nearly planar.…”

Section: Resultsmentioning

confidence: 89%

On the Structure and Chiral Aggregation of Liquid Crystalline Star‐Shaped Triazines H‐Bonded to Benzoic Acids

Feringán

Cerdá

Diosdado

et al. 2020

Chemistry A European J

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The ability of as tar-shaped tris(triazolyl)triazine derivative to hierarchically build supramolecular chiral columnar organizationst hrough the formation of H-bonded complexes with benzoic acids was studied from at heoretical and experimental point of view.T he combined study has been done at three different levels includingt he study of the structure of the triazine core, the association with benzoic acids in stoichiometry 1:3, andt he assembly of 1:3c omplexes in helical aggregates. Althought he star-shaped triazine core crystallizes in an on-C 3 conformation, the C 3-symmetric conformation is theoretically predictedt ob emore stable and gives rise to af avorable C 3 supramolecular 1:3 complex upon the interactionw ith three benzoica cids in their voids. In addition, calculations at different levels (DFT, PM7, and MM3) for the 1:3h ost-guest complex predict the formation of large stable columnar helical aggregates stabilized by the compactp ackingo ft he interstitial acids by p-p and CH•••p interactions. The acids restrict the movement of the the star-shaped triazine cores along the stacking axis causing at emplate effect in the self-assembly of the complex. Theoretical predictions correlate with experimental results,s ince the interaction with achiral or chiral 3,4,5-(4-alkoxybenzyloxy)benzoic acids gives rise to supramolecular complexes that organize in bulk hexagonal columnar mesophases stable at room temperature with intracolumnar order. The existence of supramolecular chirality in the mesophasew as determined for complexes formed by acids derived from (S)-2-octanol. Chiral aggregationwas also evidenced for complexesf ormed in dodecane.

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Section: Resultsmentioning

confidence: 89%

On the Structure and Chiral Aggregation of Liquid Crystalline Star‐Shaped Triazines H‐Bonded to Benzoic Acids

Feringán

Cerdá

Diosdado

et al. 2020

Chemistry A European J

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“…Diamines NH 2 –X–NH 2 were the starting substances for the synthesis, oligoethylene glycol diamine was obtained from ditosylate as described in [ 7 – 8 ]. The synthesis of biantennary oligoglycines was carried out by means of the activated esters method ( Scheme 1 ) [ 9 ].…”

Section: Resultsmentioning

confidence: 99%

“…Activated esters BocGlyONSu and BocGly 2 ONSu were prepared as described earlier [ 9 ] from glycine or glycylglycine (Acros). Ethylenediamine and 1,10-diaminodecane were supplied from Sigma-Aldrich, and diamine NH 2 (CH 2 CH 2 O) 3 CH 2 CH 2 NH 2 ( 1 ) was synthesized from ditosylate TosO(CH 2 CH 2 O) 3 CH 2 CH 2 OTos (Sigma–Aldrich) according to the described methods [ 7 – 8 ].…”

Section: Methodsmentioning

confidence: 99%

Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

Tsygankova¹,

Chinarev²,

Tuzikov³

et al. 2014

Beilstein J. Org. Chem.

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SummaryOligoglycines designed in a star-like fashion, so-called tri- and tetraantennary molecules, were found to form highly ordered supramers in aqueous medium. The formation of these supramers occurred either spontaneously or due to the assistance of a mica surface. The driving force of the supramer formation is hydrogen bonding, the polypeptide chain conformation is related to the folding of helical polyglycine II (PG II). Tri- and tetraantennary molecules are capable of association if the antenna length reach 7 glycine (Gly) residues. Properties of similar biantennary molecules have not been investigated yet, and we compared their self-aggregating potency with similar tri- and tetraantennary analogs. Here, we synthesized oligoglycines of the general formula R-Glyn-Х-Glyn-R (X = -HN-(СН2)m-NH-, m = 2, 4, 10; n = 1–7) without pendant ligands (R = H) and with two pendant sialoligands (R = sialic acid or sialooligosaccharide). Biantennary oligoglycines formed PG II aggregates, their properties, however, differ from those of the corresponding tri- and tetraantennary oligoglycines. In particular, the tendency to aggregate starts from Gly4 motifs instead of Gly7. The antiviral activity of end-glycosylated peptides was studied, and all capable of assembling glycopeptides demonstrated an antiviral potency which was up to 50 times higher than the activity of peptide-free glycans.

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“…Commercial compounds [Oleyl alcohol 85%, 2-bromoethylamine hydrobromide] were used as received except DIPEA which was distilled over KOH. O,O-Dioleylphosphite 5 22 and 3,5-Bis(bromomethyl)phenol 23 13 were synthesized according to a reported procedure. The mean particle diameter and zeta potential (ξ) of the liposomes and lipoplexes were measured using a Zetasizer Nano ZS (Malvern Instruments) at 25 °C (see ESI †).…”

Section: Methodsmentioning

confidence: 99%

Cationic dialkylarylphosphates: a new family of bio-inspired cationic lipids for gene delivery

et al. 2015

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In this work that aims to synthesize and evaluate new cationic lipids as vectors for gene delivery, we report the synthesis of a series of cationic lipids in which a phosphate functional group acts as a linker to assemble on a molecular scale, two lipid chains and one cationic polar head. The mono or dicationic moiety is connected to the phosphate group by an aryl spacer. In this work, two synthesis strategies were evaluated. The first used the Atherton-Todd coupling reaction to introduce a phenolic derivative to dioleylphosphite. The second strategy used a sequential addition of lipid alcohol and a phenolic derivative on POCl3. The two methods are efficient, but the latter allows larger yields. Different polar head groups were introduced, thus producing amphiphilic compounds possessing either one permanent (N-methyl-imidazolium, pyridinium, trimethylammonium) or two permanent cationic charges. All these cationic lipids were formulated as liposomal solutions and characterized (size and zeta potential). They formed stable liposomal solutions both in water (at pH 7.0) and in a weakly acidic medium (at pH 5.5). Finally, this new generation of cationic lipids was used to deliver DNA into various human-derived epithelial cells cultured in vitro. Compared with Lipofectamine used as a reference commercial lipofection reagent, some cationic dialkylarylphosphates were able to demonstrate potent gene transfer abilities, and noteworthily, monocationic derivatives were much more efficient than dicationic analogues.

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Triazole-oligomers by 1,3-dipolar cycloaddition

Abstract: A variety of triazole-oligomers have been prepared under microwave and conventional conditions from novel alkynes and azides.

Cited by 35 publications

References 8 publications

On the Structure and Chiral Aggregation of Liquid Crystalline Star‐Shaped Triazines H‐Bonded to Benzoic Acids

On the Structure and Chiral Aggregation of Liquid Crystalline Star‐Shaped Triazines H‐Bonded to Benzoic Acids

Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

Cationic dialkylarylphosphates: a new family of bio-inspired cationic lipids for gene delivery

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