Hybrids of sugars and aromatics: A Pd-catalyzed modular approach to chromans and isochromans

Leibeling, Markus; Koester, Dennis C.; Pawliczek, Martin; Kratzert, Daniel; Dittrich, Birger; Werz, Daniel B.

doi:10.1016/j.bmc.2010.03.004

Cited by 33 publications

(15 citation statements)

References 58 publications

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“…In contrast to our earlier studies, which showed limitations with respect to the substitution pattern due to the use of an intramolecular domino reaction, [9,10] our results for a much more flexible intermolecular variant are described in this report. The general idea is depicted in Scheme 1.…”

Section: Markus Leibelingcontrasting

confidence: 81%

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Intermolecular Twofold Carbopalladation/Cyclization Sequence to Access Chromans and Isochromans from Carbohydrates

Leibeling

Milde

Kratzert

et al. 2011

Chemistry A European J

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Section: Markus Leibelingcontrasting

confidence: 81%

“…[12,13,14] The starting material is a 2-bromoglycal that can be easily derived from the native monosaccharide in several steps. [10,15] This six-membered ring can be employed either to give chroman-or isochroman-type structures. In the former case, an alkynyl chain is attached to C3, in the latter to C1.…”

Section: Markus Leibelingmentioning

confidence: 99%

Intermolecular Twofold Carbopalladation/Cyclization Sequence to Access Chromans and Isochromans from Carbohydrates

Leibeling

Milde

Kratzert

et al. 2011

Chemistry A European J

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“…The importance of 2‐haloglycals has been very well demonstrated by Werz and co‐workers5,13 in the synthesis of annulated sugars through metal‐catalyzed coupling reactions. As a result of the relevance of these important sugar intermediates, the synthesis of 2‐ C ‐aryl‐glycoside 21 from 2‐iodoglucal 20 through phosphine‐free Suzuki–Miyaura cross‐coupling in aqueous media has recently been reported by Boutureira and Davis 14.…”

Section: 2‐c‐branched Carbohydratesmentioning

confidence: 94%

Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates

Vankar

Linker

2015

Eur J Org Chem

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The importance of carbohydrate chemistry in biological and medicinal chemistry has led to enormous developments in the synthesis of carbohydrate mimics. In this context, the synthesis of branched sugars in general and of 2‐C‐branched carbohydrates in particular, as well as the synthesis of 1,2‐annulated sugars, have received immense attention. They serve not only as carbohydrate mimics in the form of stand‐alone molecules, but also as useful intermediates in the synthesis of many natural products, their analogues, and glycosidase inhibitors. This microreview covers the recent synthetic efforts in this area and puts the subject matter into proper perspective for future developments.

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“…However, the drawback associated with use of carbohydrates as drug scaffolds is their metabolism by native enzymes in the body 43,44 . A potentially useful approach to circumvent this drawback could be achieved after synthesis of hybrid molecules with a sugar and a non-sugar domain fused or linked together, possessing druggable properties that may avoid enzymatic breakdown in the body [45][46][47][48][49][50][51] . The mounting realization of the potential biological significance of sugar-based hybrid molecules has prompted a number of chemists to attempt their synthesis in recent years.…”

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confidence: 99%

Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents

Kumari

Mishra

Narayana

et al. 2020

Sci Rep

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C-glycosides are important class of molecules exhibit diverse biological activities and present as structural motif in many natural products. Two series of new pyrazoline and isoxazole bridged indole C-glycoside molecular hybrids (n = 36) were efficiently synthesized starting from diverse indole 3-carboxaldehydes derived α, β-unsaturated ketone derivatives of β-D-glucosyl-propan-2-one, β-D-galactosyl-propan-2-one and β-D-mannosyl-propan-2-one, reacting with hydrazine hydrate and hydroxyl amine hydrochloride in shorter reaction time (15 min) under microwave assisted condition. Anticancer activity of these newly synthesized pyrazoline and isoxazole bridged indoles C-glycoside hybrids were determined in details through cellular assays against MCF-7, MDA-MB-453 and MDA-MB-231 cancer cell lines. The selected library members displayed low micromolar (IC 50 = 0.67-4.67 µM) and selective toxicity against breast cancer cell line (MCF-7). Whereas these compounds were nontoxic towards normal cell line (MCF-10A). Mechanistic studies showed that, active compounds inhibit COX-2 enzyme, which was also supported by molecular docking studies. These findings are expected to provide new leads towards anticancer drug discovery.C-Glycosides are stable surrogates of O-glycosides and are often used as investigative tool in chemical biology and medicinal chemistry, in particular C-glycoside analogues are often used as substrate mimics for different enzymes involved in the carbohydrate metabolism 1-10 . The use of glycomimetic in the design of inhibitors has proven to be a successful approach and now constitutes one of the most attractive ways to develop new generations of effective and selective inhibitors 11 . α, β-unsaturated ketone is a central core for many significant biological compounds 12,13 . According to literature α, β-unsaturated ketone derivatives from natural and synthetic analogues exhibit diverse pharmacological activities such as anti-tuberculosis, anti-inflammatory, anticancer, antineoplastic, antibacterial, antifungal, antimalarial, antiviral, antiallergic, estrogenic 12 and COX-2 inhibitor 13 .Pyrazoline derivatives are important biologically active heterocyclic compounds. These derivatives are the subject of many research studies due to their widespread potential biological activities such as anticancer, antioxidant, antibacterial activities 14 and COX-2 inhibitor 15 . The most prominent compounds containing pyrazoline nucleus are ampyrone, phenazone and propyphenzone. Isoxazole heterocycle is well known for its medicinal relevance 16,17 . There are isoxazole nucleus containing drug molecules currently available in market, such as acetylsulfisoxazole, cycloserine, sulfisoxazole, and zonisamide etc. These drugs possess antimicrobial 18 , antioxidant 19,20 tuberculostatic 21 neurotoxic 22 , antiepileptic activities 23,24 and COX-2 inhibitor 25 . The comparable activities are also observed in other isoxazole derivatives, captivates researcher to search for newer bioactive compounds of using this as pharmacophore. α, β-...

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Hybrids of sugars and aromatics: A Pd-catalyzed modular approach to chromans and isochromans

Cited by 33 publications

References 58 publications

Intermolecular Twofold Carbopalladation/Cyclization Sequence to Access Chromans and Isochromans from Carbohydrates

Intermolecular Twofold Carbopalladation/Cyclization Sequence to Access Chromans and Isochromans from Carbohydrates

Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates

Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents

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