Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation

Miura, Yoshiko; Onogi, Shunsuke; Fukuda, Tomohiro

doi:10.3390/molecules171011877

Cited by 14 publications

(5 citation statements)

References 31 publications

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“…The substituted coumarins ( 1a – e ) were then reacted with 1,2-dibromoethane, 1,3-dibromopropane or 3-bromo-1-propyne, respectively, to give 2a – e , 3a – e , 4a – e , 7a , 7b , and 9a were obtained by dihydroartemisinin(DHA) reacted with 2-bromoethanol, 3-bromo-1-propanol, or 3-bromo-1-propyne, respectively, as β configuration (indicated by the small coupling constants between 9-H and 10-H in 1 H NMR, J 9,10 = 3–4 Hz [20]) by using boron trifluoride ethyl ether as a catalyst [21]. Further azidation of 2a – e , 3a – e , 7a , and 7b gave compounds 5a – e , 6a – e , 8a , and 8b [22].…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry

Tian

Liang

et al. 2016

Molecules

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Abstract:In order to develop novel chemotherapeutic agents with potent anticancer activities, we designed four series of novel compounds employing hybridization strategy. Twenty novel dihydroartemisinin-coumarin hybrids, 10a-e, 11a-e, 12a-e, 13a-e, were synthesized via click chemistry in this study and their structures were characterized by HRMS and NMR. The cytotoxic activities were measured by MTT assay against three cancer cell lines (HCT-116, MDA-MB-231, and HT-29) under normoxic or anoxic conditions, respectively. The target compounds exhibited moderate activity with IC 50 values in the 0.05-125.40 µM range, and these compounds exhibited better activity against HT-29 cell line under anoxic condition. The cytotoxic activities of most compounds under anoxic condition displayed one-to 10-fold greater activity than under normoxic condition. Compounds 10a-e showed better selectivity against the HT-29 cell line than the other two cell lines. These results indicated that our design of CA IX inhibitors does correspond with its action mode to some degree and deserves further investigation.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry

Tian

Liang

et al. 2016

Molecules

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“…Starting materials 1,4-di(chloromethyl)benzene and 1,3,5-tri(chloromethyl)benzene were prepared according to a literature procedure and purified by sublimation in vacuo (10 –3 mbar, 60 °C) before further use .…”

Section: Methodsmentioning

confidence: 99%

Introducing Benzene-1,3,5-tri(dithiocarboxylate) as a Multidentate Linker in Coordination Chemistry

et al. 2021

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Benzene-1,3,5-tri(dithiocarboxylate) (BTDTC3–), the sulfur-donor analogue of trimesate (BTC3–, benzene-1,3,5-tricarboxylate), is introduced, and its potential as a multidentate, electronically bridging ligand in coordination chemistry is evaluated. For this, the sodium salt Na3BTDTC has been synthesized, characterized, and compared with the sodium salt of the related ditopic benzene-1,4-di(dithiocarboxylate) (Na2BDDTC). Single-crystal X-ray diffraction of the respective tetrahydrofuran (THF) solvates reveals that such multitopic aromatic dithiocarboxylate linkers can form both discrete metal complexes (Na3BTDTC·9THF) and (two-dimensional) coordination polymers (Na2BDDTC·4THF). Additionally, the versatile coordination behavior of the novel BTDTC3– ligand is demonstrated by successful synthesis and characterization of trinuclear Cu(I) and hexanuclear Mo(II)2 paddlewheel complexes. The electronic structure and molecular orbitals of both dithiocarboxylate ligands as well as their carboxylate counterparts are investigated by density functional theory computational methods. Electrochemical investigations suggest that BTDTC3– enables electronic communication between the coordinated metal ions, rendering it a promising tritopic linker for functional coordination polymers.

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“…In recent years, click chemistry has been applied to the syntheses of dendrimers. Expanding the use of click reactions to dendrimers can contribute to the development of dendrimer science [19][20][21][22][23][24]. However, the application of Huisgen cycloaddition to triazine dendrimers has not been reported to date.…”

Section: Introductionmentioning

confidence: 99%

Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity

et al. 2022

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Dendrimers are attractive macromolecules for a broad range of applications owing to their well-defined shapes and dimensions, highly branched and globular architectures, and opportunities for exploiting multivalency. Triazine dendrimers in particular offer advantages such as ease of synthesis, stability, well-defined spherical structure, multivalency, potential to achieve acceptable drug loadings, and low polydispersity. In this study, the potential utility of alkyne-azide “click” cycloadditions of first-, second-, and third-generation triazine dendrimers containing three or six alkynyl groups with benzyl azide was examined using copper catalysts. “Click-and-grow” and “grow-then-click” strategies were employed. For the first- and second- generation dendrimers, the desired triazole derivatives were obtained in high yields and purified by simple reprecipitation without column chromatography; however, some difficulties were observed in the preparation of third-generation dendrimers. The desired reaction proceeded under microwave irradiation as well as with simple heating. This click chemistry can be utilized for various melamine dendrimers that are fabricated with other amine linkers.

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Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation

Cited by 14 publications

References 31 publications

Design, Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry

Design, Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry

Introducing Benzene-1,3,5-tri(dithiocarboxylate) as a Multidentate Linker in Coordination Chemistry

Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity

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