MDPI - Publisher of Open Access Journals

4 pages, 260 KiB

Open AccessProceeding Paper

Green, Microwave-Assisted Synthesis of O-Perbutyrylated-Alkyl-Glycosides

by Emmanuel Pérez-Escalante, Luis Guillermo González-Olivares, Araceli Castañeda-Ovando, Verónica Salazar-Pereda, John F. Trant, Mirandeli Bautista-Ávila and Sergio Alatorre-Santamaría

Proceedings 2019, 41(1), 42; https://doi.org/10.3390/ecsoc-23-06500 - 14 Nov 2019

Viewed by 1108

Abstract

Chemical synthesis of carbohydrates is a challenging task. Several protection and deprotection steps of hydroxyl groups are required to ensure regioselective formation of the glycosidic bond. Usually, it is achieved through acylation, where conventional heating is combined with addition of Lewis acids as catalysts. This traditional approach has two drawbacks; it is time consuming and often catalysts are hazardous to the environment. An alternative route relies on application of microwaves and/or other Lewis acids with less or no toxicity. Such combination would reduce reaction times and offer a benign synthetic strategy to obtain peracylated compounds. The current work describes an efficient and environmentally mild synthesis of peracylated glycosides with potential application in enzymatic preparation of carbohydrates. Model compound O-perbutyrylated-phenyl-galactose was synthesized using imidazole as catalyst in the microwave-assisted process. The acylation protocol was optimized, and the target sugar was obtained at 50% yield after 1 h. In conclusion, the combination of imidazole and microwaves provides an excellent alternative to swiftly synthesize peracylated glycosides in a benign way. Full article

(This article belongs to the Proceedings of The 23rd International Electronic Conference on Synthetic Organic Chemistry)

► Show Figures

Figure 1

26 pages, 911 KiB

Open AccessArticle

Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives

by Cheng-Ting Zi, Zhen-Hua Liu, Gen-Tao Li, Yan Li, Jun Zhou, Zhong-Tao Ding, Jiang-Miao Hu and Zi-Hua Jiang

Molecules 2015, 20(2), 3255-3280; https://doi.org/10.3390/molecules20023255 - 16 Feb 2015

Cited by 18 | Viewed by 6573

Abstract

A series of novel perbutyrylated glycosides of 4β-triazolopodophyllotoxin derivatives were synthesized by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Evaluation of cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using the MTT assay shows that some of these glycosylated derivatives have good anticancer activity. Among the synthesized compounds, compound 21a shows the highest activity, with IC₅₀ values ranging from 0.49 to 6.70 μM, which is more potent than the control drugs etoposide and cisplatin. Compound 21a is characterized by a perbutyrylated α-D(+)-galactosyl residue, the absence of an additional linking spacer between the sugar residue and the triazole ring, as well as a 4'-OH group on the E ring of the podophyllotoxin scaffold. Full article

(This article belongs to the Section Medicinal Chemistry)

► Show Figures

Graphical abstract

Search Results (2)

Further Information

Guidelines

MDPI Initiatives

Follow MDPI

Saved Queries

Search Filter Reset All

Years

Feature Papers

Subjects

Journals

Article Types

Countries / Regions

Search Results (2)

Further Information

Guidelines

MDPI Initiatives

Follow MDPI