Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity was written by Kaur Gulati, Harmandeep;Choudhary, Sushil;Kumar, Nitish;Ahmed, Ajaz;Bhagat, Kavita;Vir Singh, Jatinder;Singh, Atamjit;Kumar, Ajay;Singh Bedi, Preet Mohinder;Singh, Harbinder;Mukherjee, Debaraj. And the article was included in Bioorganic Chemistry in 2022.Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate The following contents are mentioned in the article:
Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen’s [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated, e.g. I, and free sugar hydroxyl groups at the amino position of tacrine were synthesized in good yield taking aid from mol. docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200μM (100% cell viability) as compared to tacrine (35% cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series I (IC50 0.4μM) revealed its mixed inhibition approach. Thus, compound I can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer’s disease (AD) which stands as an adequate chem. probe to be launched in an AD drug discovery program. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate).
(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
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