Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations

Brusentzeva, Olga I.; Kharitonov, Yurii V.; Fadeev, Dmitry S.; Шульц, Э. Э.

doi:10.1007/s10847-019-00965-z

Cited by 4 publications

(3 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Regularities of behavior in aqueous solutions with temperature variation were established for PAlOx, and features that distinguish them from other thermosensitive polymers were revealed [ 28 , 29 , 30 , 31 , 32 , 33 , 34 ]. It has been found that the introduction of fragments ready for effective binding of inorganic ions and organic compounds, for example, azamacrocycles, is an effective strategy for the construction of supramolecular structures, thereby allowing to simulate the processes occurring in living nature [ 35 , 36 , 37 ].…”

Section: Introductionmentioning

confidence: 99%

Influence of Salt on the Self-Organization in Solutions of Star-Shaped Poly-2-alkyl-2-oxazoline and Poly-2-alkyl-2-oxazine on Heating

et al. 2021

View full text Add to dashboard Cite

The water–salt solutions of star-shaped six-arm poly-2-alkyl-2-oxazines and poly-2-alkyl-2-oxazolines were studied by light scattering and turbidimetry. The core was hexaaza[26]orthoparacyclophane and the arms were poly-2-ethyl-2-oxazine, poly-2-isopropyl-2-oxazine, poly-2-ethyl-2-oxazoline, and poly-2-isopropyl-2-oxazoline. NaCl and N-methylpyridinium p-toluenesulfonate were used as salts. Their concentration varied from 0–0.154 M. On heating, a phase transition was observed in all studied solutions. It was found that the effect of salt on the thermosensitivity of the investigated stars depends on the structure of the salt and polymer and on the salt content in the solution. The phase separation temperature decreased with an increase in the hydrophobicity of the polymers, which is caused by both a growth of the side radical size and an elongation of the monomer unit. For NaCl solutions, the phase separation temperature monotonically decreased with growth of salt concentration. In solutions with methylpyridinium p-toluenesulfonate, the dependence of the phase separation temperature on the salt concentration was non-monotonic with minimum at salt concentration corresponding to one salt molecule per one arm of a polymer star. Poly-2-alkyl-2-oxazine and poly-2-alkyl-2-oxazoline stars with a hexaaza[26]orthoparacyclophane core are more sensitive to the presence of salt in solution than the similar stars with a calix[n]arene branching center.

show abstract

Section: Introductionmentioning

confidence: 99%

Influence of Salt on the Self-Organization in Solutions of Star-Shaped Poly-2-alkyl-2-oxazoline and Poly-2-alkyl-2-oxazine on Heating

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[13,14,17,18] The synthetic chemistry of tricyclic diterpenoids is a currently emerging area. In a series of macroheterocyclic derivatives based on accessible labdane diterpenoid lambertianic acid [19][20][21][22][23][24] compounds with significant cytotoxicity to human tumor cells, [22] and also mercury(II) [21] or zinc(II) ion complexants have been identified. [24] As a common synthetic approach to preparing macroheterocyclic diterpenoids the Cu-catalyzed azide alkyne cycloaddition (CuAAC) reaction was successfully used.…”

Section: Introductionmentioning

confidence: 99%

Click Synthesis of Triazole-Linked Polyazamacrocycles through Selective Isopimaric Acid Transformations

Gromova¹,

Kharitonov²,

Рыбалова³

et al. 2021

MHC

Self Cite

View full text Add to dashboard Cite

The first macrocyclic pimarane type diterpenoids containing fragments of 1,2,3-triazole and tricyclic diterpenoid isopimaric acid moieties were synthesized. The key step was the CuAAC reaction of various diazides with the dialkyne derivative obtained from 16-(carboxyphenyl)isopimaric acid. The molecular structure of the macrocyclic compound with 1,5-diazopentane unit was determined by single crystal X-ray diffraction analysis.

show abstract

“…[25] 1,2,3-Triazole found application in the structural modification of natural products. [26] We have recently shown that the CuAAC reaction of labdane type [27][28][29][30][31] and pimarane-type [32] diacetylenes with various diazides led to optically active 1,2,3-triazolecontaining macroheterocyclic diterpenoids in good yields. Among the synthesized macrocyclic compounds, substances were found that have high cytotoxicity to human tumor cells.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Macrocyclic Peptide-Diterpenoid Conjugates by a Sequential Arylation/Peptide Coupling/Click Macrocyclization Procedure

Gromova¹,

Kharitonov²,

Golubeva³

et al. 2021

MHC

Self Cite

View full text Add to dashboard Cite

An approach relying on a sequential selective arylation of isopimaric acid/peptide coupling/CuAAC-based macrocyclization procedure of alkynyl peptides to azidoditerpenoid, was developed for the preparation of novel triazole-linked peptide -tricyclic diterpenoid conjugates. The process has comprised the synthesis of azidoditerpenoid bearing the azido group at the side chain by the cross-coupling reaction of isopimaric acid with 1-azido-2-iodobenzene as well as the preparation of a small library of dipeptides featuring varied amino acid sequence (Gly-Gly, Gly-Val, Val-Gly and Val-Val). This approach has shown great chemical efficiency and gave macrocyclic compounds in good yields. It was shown that the yield of macrocyclization products depends on the substituent in the dipeptide fragment. The cytotoxicity of the synthesized compounds was evaluated using the conventional MTT assays. It has been found that the introduction of a dipeptide fragment into the structure of isopimaric acid and macrocyclization have a significant effect on toxicity towards human cancer cells

show abstract

Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations

Cited by 4 publications

References 25 publications

Influence of Salt on the Self-Organization in Solutions of Star-Shaped Poly-2-alkyl-2-oxazoline and Poly-2-alkyl-2-oxazine on Heating

Influence of Salt on the Self-Organization in Solutions of Star-Shaped Poly-2-alkyl-2-oxazoline and Poly-2-alkyl-2-oxazine on Heating

Click Synthesis of Triazole-Linked Polyazamacrocycles through Selective Isopimaric Acid Transformations

Synthesis of Macrocyclic Peptide-Diterpenoid Conjugates by a Sequential Arylation/Peptide Coupling/Click Macrocyclization Procedure

Contact Info

Product

Resources

About