EDC/DMAP-mediated direct condensation of dicarboxylic acids and diols: A concise synthesis of extra large polyether macrocyclic lactones and their X-ray structures

Naveen, _______; Babu, Srinivasarao Arulananda

doi:10.1016/j.tetlet.2016.11.046

Cited by 10 publications

(4 citation statements)

References 78 publications

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“…The amide and ester functional groups containing alkynes 1e , 1f, 1g , and 1k (Figure ) were freshly prepared by coupling the propargylamine or propargyl alcohol with carboxylic acids through the well-known standard EDC/DMAP coupling reaction . Both O and N -propargyl alkynes 1c, 1h, 1i, 1m , and 1l were prepared by alkylating the phenolic hydroxyl group or amide −NH by propargyl bromide using sodium hydride .…”

Section: Methodsmentioning

confidence: 99%

Chemoenzymatic and Protecting-Group-Free Synthesis of 1,4-Substituted 1,2,3-Triazole-α-d-glucosides with Potent Inhibitory Activity toward Lysosomal α-Glucosidase

et al. 2021

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α-Glucosyl triazoles have rarely been tested as α-glucosidase inhibitors, partly due to inefficient synthesis of their precursor α-d-glucosylazide (αGA1). Glycosynthase enzymes, made by nucleophile mutations of retaining β-glucosidases, produce αGA1 in chemical rescue experiments. Thermoanaerobacterium xylanolyticus glucosyl hydrolase 116 β-glucosidase (TxGH116) E441G nucleophile mutant catalyzed synthesis of αGA1 from sodium azide and pNP-β-d-glucoside (pNPGlc) or cellobiose in aqueous medium at 45 °C. The pNPGlc and azide reaction product was purified by Sephadex LH-20 column chromatography to yield 280 mg of pure αGA1 (68% yield). αGA1 was successfully conjugated with alkynes attached to different functional groups, including aryl, ether, amine, amide, ester, alcohol, and flavone via copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry reactions. These reactions afforded the 1,4-substituted 1,2,3-triazole-α-d-glucoside derivatives AGT2-14 without protection and deprotection. Several of these glucosyl triazoles exhibited strong inhibition of human lysosomal α-glucosidase, with IC50 values for AGT4 and AGT14 more than 60-fold lower than that of the commercial α-glucosidase inhibitor acarbose.

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Section: Methodsmentioning

confidence: 99%

Chemoenzymatic and Protecting-Group-Free Synthesis of 1,4-Substituted 1,2,3-Triazole-α-d-glucosides with Potent Inhibitory Activity toward Lysosomal α-Glucosidase

et al. 2021

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“…48 Based on the above molecular design concepts, six maleimide-based macrocyclic lactone enediynes were designed and synthesized in the present work. Firstly, the terminal dialkynes were prepared by an esterification reaction, [55][56][57][58] and then the macrocyclic enediynes (EDY A-F) were obtained through the Sonogashira cross-coupling reaction 59 between maleimide diiodide and the corresponding dialkynes at room temperature (Scheme 1). Among them, EDY-A, B, and C have different ring sizes (12-, 13-, and 14-membered, respectively), while EDY-D, E, and F are 13-membered enediynes with different substituents at the propargyl position.…”

Section: Design and Synthesis Of Maleimide-based Macrocyclic Enediynementioning

confidence: 99%

Synthesis and biological properties of maleimide-based macrocyclic lactone enediynes

Lü

et al. 2022

Org. Biomol. Chem.

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“…It has been shown that α,ω-alka-nZ,(n+4)Z-dienediols (1,12-dodeca-4Z,8Z-dienediol (4a), 1,14-tetradeca-5Z,9Z-dienediol (4b), 1,18-octadeca-7Z,11Z-dienediol (4c)), and aromatic dicarboxylic acids (5a-c) can be involved in intermolecular cyclocondensation mediated by DMAP and EDC•HCl [31,32].…”

Section: Chemistrymentioning

confidence: 99%

Direct Synthesis of Polyaromatic Cyclophanes Containing Bis-Methylene-Interrupted Z-Double Bonds and Study of Their Antitumor Activity In Vitro

D’yakonov

Islamov

Dzhemileva

et al. 2021

IJMS

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An original synthetic route was developed for the preparation of previously unknown unsaturated polyaromatic macrolactones containing a 1Z,5Z-diene moiety in 48–71% yields and with >98% stereoselectivity. The method is based on intermolecular cyclocondensation of aromatic dicarboxylic acids with α,ω-alka-nZ,(n+4)Z-dienediols (1,12-dodeca-4Z,8Z-dienediol, 1,14-tetradeca-5Z,9Z-dienediol, 1,18-octadeca-7Z,11Z-dienediol) mediated by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC)/4-dimethylaminopyridine (DMAP). The unsaturated diols were prepared by successive homo-cyclomagnesiation of tetrahydropyran ethers of O-containing 1,2-dienes with EtMgBr in the presence of Mg metal and the Cp2TiCl2 catalyst (10 mol.%) and subsequent treatment with 0.1 equiv. of para-toluenesulfonic acid of pyran ethers formed after the acid hydrolysis of magnesacyclopentanes. The resulting cyclophanes exhibited high cytotoxic activity in vitro against Jurkat, K562, U937, and HL60 cancer lines. Additionally, the synthesized products were studied for their effect on mitochondria, ability to induce apoptosis, and influence on the cell cycle using modern flow cytometry methods.

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EDC/DMAP-mediated direct condensation of dicarboxylic acids and diols: A concise synthesis of extra large polyether macrocyclic lactones and their X-ray structures

Cited by 10 publications

References 78 publications

Chemoenzymatic and Protecting-Group-Free Synthesis of 1,4-Substituted 1,2,3-Triazole-α-d-glucosides with Potent Inhibitory Activity toward Lysosomal α-Glucosidase

Chemoenzymatic and Protecting-Group-Free Synthesis of 1,4-Substituted 1,2,3-Triazole-α-d-glucosides with Potent Inhibitory Activity toward Lysosomal α-Glucosidase

Synthesis and biological properties of maleimide-based macrocyclic lactone enediynes

Direct Synthesis of Polyaromatic Cyclophanes Containing Bis-Methylene-Interrupted Z-Double Bonds and Study of Their Antitumor Activity In Vitro

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