scholarly journals Approaches to the Synthesis of Glycosides

2021 ◽  
Author(s):  
◽  
Richard Hubert Furneaux
Keyword(s):  
Ascorbic Acid ◽  
Hydrogen Sulphide ◽  
Boron Trifluoride ◽  
Synthetic Route ◽  
One Step ◽  
Synthetic Routes ◽  
Alpha Beta ◽  
Derivatives Of ◽  
Carbonyl Function

<p>In a search for better synthetic routes to O- and S-glycosides, a number of mercury(II) containing derivatives of 1-thio-D-glucose were synthesised, and their reactions with thiols and acids were investigated as well as their pyrolytic behaviour. A new route to O-acetylated glycosyl thiols involving specific S-deacetylation of peracetylated 1-thioglycoses was developed by the conversion of 1-thio-Beta-D-glucopyranose pentaacetate into tetra-O-acetyl-1-S-phenylmercury (II) thio-Beta-D-glucopyranose and subsequent demercuration of this by hydrogen sulphide. A range of acylated alkyl and aryl 1,2-trans-1-thioglycosides was prepared by one step processes from peracylated 1,2-trans-related sugars by a procedure which involved the use of equimolar proportions of thiols together with boron trifluoride. A similar procedure was used to obtain benzoylated 1,2-cis-O-glucosides from penta-O-benzoyl-Beta-D-glucopyranose. Partial desulphurisation of acetylated glucosyl phenyl disulphide with tris(diethylamino)phosphine led to both phenyl tetra-O-acetyl-1-thio-alpha-D-glucopyranoside and the alpha, beta-linked thiotrehalose peracetate. Phenyl 1-thiohex-1-enopyranosid-3-ulose esters were obtained from the light induced reactions of N-bromosuccinimide with acetylated and benzoylated phenyl 1-thiogluco- and galacto-pyranosides; the acetylated 1-thioglycosides gave mixtures of 2-O-acetyl and 2-O-monobromoacetyl 1-enosid-3-uloses. Methyl hexuronate derivatives were brominated alpha to the carbonyl function by N-bromosuccinimide, and a new synthetic route to L-ascorbic acid has been proposed following the successful bromination of methyl tri-O-acetyl-2,6-anhydro-L-gulonate.</p>

scholarly journals Approaches to the Synthesis of Glycosides

2021 ◽  
Author(s):  
◽  
Richard Hubert Furneaux
Keyword(s):  
Ascorbic Acid ◽  
Hydrogen Sulphide ◽  
Boron Trifluoride ◽  
Synthetic Route ◽  
One Step ◽  
Synthetic Routes ◽  
Alpha Beta ◽  
Derivatives Of ◽  
Carbonyl Function

<p>In a search for better synthetic routes to O- and S-glycosides, a number of mercury(II) containing derivatives of 1-thio-D-glucose were synthesised, and their reactions with thiols and acids were investigated as well as their pyrolytic behaviour. A new route to O-acetylated glycosyl thiols involving specific S-deacetylation of peracetylated 1-thioglycoses was developed by the conversion of 1-thio-Beta-D-glucopyranose pentaacetate into tetra-O-acetyl-1-S-phenylmercury (II) thio-Beta-D-glucopyranose and subsequent demercuration of this by hydrogen sulphide. A range of acylated alkyl and aryl 1,2-trans-1-thioglycosides was prepared by one step processes from peracylated 1,2-trans-related sugars by a procedure which involved the use of equimolar proportions of thiols together with boron trifluoride. A similar procedure was used to obtain benzoylated 1,2-cis-O-glucosides from penta-O-benzoyl-Beta-D-glucopyranose. Partial desulphurisation of acetylated glucosyl phenyl disulphide with tris(diethylamino)phosphine led to both phenyl tetra-O-acetyl-1-thio-alpha-D-glucopyranoside and the alpha, beta-linked thiotrehalose peracetate. Phenyl 1-thiohex-1-enopyranosid-3-ulose esters were obtained from the light induced reactions of N-bromosuccinimide with acetylated and benzoylated phenyl 1-thiogluco- and galacto-pyranosides; the acetylated 1-thioglycosides gave mixtures of 2-O-acetyl and 2-O-monobromoacetyl 1-enosid-3-uloses. Methyl hexuronate derivatives were brominated alpha to the carbonyl function by N-bromosuccinimide, and a new synthetic route to L-ascorbic acid has been proposed following the successful bromination of methyl tri-O-acetyl-2,6-anhydro-L-gulonate.</p>

Two in one: bifunctional derivatives of trolox acting as antimalarial and antioxidant agents

2020 ◽  
Vol 12 (20) ◽  
pp. 1845-1854
Author(s):  
Florence Souard ◽  
Edwige Nicolle ◽  
Delphine Cressend ◽  
Alexis Valentin ◽  
Ahcène Boumendjel
Keyword(s):  
Antioxidant Activity ◽  
Ascorbic Acid ◽  
In Vivo Studies ◽  
Chemical Libraries ◽  
Falciparum Strain ◽  
Antioxidant Agents ◽  
One Step ◽  
Set Up ◽  
Derivatives Of

Background: The aim of the present work was to set-up compounds that are able to act simultaneously as antimalarial and antioxidants. Trolox, a known antioxidant was chosen as a core structure to ensure the antioxidant activity and contribute to antiplasmodial effect. Results: Ten compounds were prepared in one step and evaluated on chloroquino-sensitive (3D7) and chloroquino-resistant (FcB1) strains of Plasmodium falciparum. The most active compound (3d) shows antiplasmodial activity in the range of chloroquine against chloroquino-sensitive and chloroquino-resistant P. falciparum strain. The antioxidant activity of (3d) was conducted through four tests and was found to be more potent than trolox itself and L-ascorbic acid. Conclusion: Compound (3d) can be considered as an excellent lead molecule for further in vivo studies. This study paves the way for building large chemical libraries to be investigated in the field of malaria.

Three-Component [1+1+1] Cyclopropanation with Ruthenium(II)

2018 ◽  
Author(s):  
Tanner C. Jankins ◽  
Robert R. Fayzullin ◽  
Eugene Khaskin
Keyword(s):  
Quaternary Carbon ◽  
Poor Control ◽  
One Step ◽  
Synthetic Routes ◽  
Mechanistic Investigations ◽  
Chiral Centers ◽  
Metal Catalyzed ◽  
The Right ◽  
Substituted Cyclopropanes

We report a one-step, Ru(II)-catalyzed cyclopropanation reaction that is conceptually different from the previously reported protocols that include Corey-Chaykovsky, Simmons-Smith, and metal catalyzed carbene attack on olefins. Under the current protocol, various alcohols are transformed into sulfone substituted cyclopropanes with excellent isolated yields and diastereoselectivities. This new reaction forms highly congested cyclopropane products with three new C–C bonds, three or two new chiral centers and one new quaternary carbon center. 22 examples of isolated substrates are given. Previously reported synthetic routes for similar substrates are all multi-step, linear routes that proceed with overall low yields and poor control of stereochemistry. Experimental mechanistic investigations suggest initial metal-catalyzed dehydrogenation of the alcohol substrate and catalyst independent stepwise attack of two equivalents of sulfone on the aldehyde under basic conditions. While the Ru(II) is only responsible for the initial dehydrogenation step, the rate of aldehyde formation is crucial to maintaining the right balance of intermediates needed to afford the cyclopropane product.

Potentials of Diphenyl Ether Scaffold as a Therapeutic Agent: A Review

2019 ◽  
Vol 19 (17) ◽  
pp. 1392-1406
Author(s):  
Suvarna G. Kini ◽  
Ekta Rathi ◽  
Avinash Kumar ◽  
Varadaraj Bhat
Keyword(s):  
Therapeutic Agent ◽  
Diphenyl Ether ◽  
Biological Properties ◽  
Industrial Applications ◽  
Synthetic Route ◽  
Structure Activity ◽  
Diphenyl Ethers ◽  
Antiviral Activities ◽  
Synthetic Routes ◽  
The 19Th Century

Diphenyl ethers (DPE) and its analogs have exhibited excellent potential for therapeutic and industrial applications. Since the 19th century, intensive research is perpetuating on the synthetic routes and biological properties of DPEs. Few well-known DPEs are Nimesulide, Fenclofenac, Triclosan, Sorafenib, MK-4965, and MK-1439 which have shown the potential of this moiety as a lead scaffold for different pharmacological properties. In this review, we recapitulate the diverse synthetic route of DPE moiety inclusive of merits and demerits over the classical synthetic route and how this moiety sparked an interest in researchers to discern the SAR (Structure Activity Relationship) for the development of diversified biological properties of DPEs such as antimicrobial, antifungal, antiinflammatory & antiviral activities.

scholarly journals Non-Nucleoside Agonists of the Adenosine Receptors: An Overview

2019 ◽  
Vol 12 (4) ◽  
pp. 150 ◽  
Author(s):  
Dal Ben ◽  
Lambertucci ◽  
Buccioni ◽  
Martí Navia ◽  
Marucci ◽  
...  
Keyword(s):  
Adenosine Receptors ◽  
Biological Activities ◽  
Great Majority ◽  
Synthetic Route ◽  
Wide Range ◽  
Pharmacological Interest ◽  
Molecular Modeling Studies ◽  
Synthetic Routes ◽  
Alternative Set ◽  
Structural Classes

Potent and selective adenosine receptor (AR) agonists are of pharmacological interest for the treatment of a wide range of diseases and conditions. Among these derivatives, nucleoside-based agonists represent the great majority of molecules developed and reported to date. However, the limited availability of compounds selective for a specific AR subtype (i.e., A2BAR) and a generally long and complex synthetic route for largely substituted nucleosides are the main drawbacks of this category of molecules. Non-nucleoside agonists represent an alternative set of compounds able to stimulate the AR function and based on simplified structures. This review provides an updated overview on the structural classes of non-nucleoside AR agonists and their biological activities, with emphasis on the main derivatives reported in the literature. A focus is also given to the synthetic routes employed to develop these derivatives and on molecular modeling studies simulating their interaction with ARs.

2-C-derivatives of L-ascorbic acid (review)

1993 ◽  
Vol 27 (1) ◽  
pp. 25-42
Author(s):  
M. N. Preobrazhenskaya ◽  
I. L. Plikhtyak
Keyword(s):  
Ascorbic Acid ◽  
Derivatives Of
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