Introducing Lipophilicity to (Polyhydroxyalkyl)thiazolidine Carboxylic Acids Via Acylation

Abstract

The therapeutic efficacy of bioactive compounds is related to their bioavailability. In turn, the bioavailability depends on the equilibrium between the hydrophilicity and the lipophilicity. 2( R,S )-(Polyhydroxyalkyl)thiazolidine-4( R ) carboxylic acids (TCAs), obtained from the condensation of l -cysteine and an aldose, have been recognized as nontoxic precursors of glutathione with important preventive and therapeutic effects. The bioavailability of these compounds can be improved by enhancing their lipophilicity. This can be achieved by the introduction of some acyl groups derived from fatty acids via esterification of the aldose hydroxyl groups. With this purpose four new compounds were synthesized through a selective palmitoyl acylation of d -(−)-ribose and d -(+)-glucose and subsequent condensation with l -cysteine. In addition, the log P of the new compounds was calculated as a measure of the lipophilicity, and in vitro 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) tests were performed as a measure of the antioxidant capability.

Modifying Fraction Extracted From Sesewanua (Clerodendrum Fragrans Wild) Leaves in Snedds Preparations: Characterization and Bioavailability Test

“…Using acyl chloride derivatives is a method for adding structures to form ester groups that enhance the lipophilicity of compounds. The greater the lipophilicity of a compound, the easier the rate of penetrating the stomach and intestinal membranes [13,14]. The analgesic efficacy of pinostrobin isolated from cat encounters has been structurally modified using acyl chloride, including acetyl, propanoyl, butyryl, and pentanoyl chloride.…”

Discovery of Potent N-Methylcarbamoylguanidino Insect Growth Regulators Targeting OfChtI and OfChi-h

“…Lipophilicity contributes to the absorption and distribution characteristics of compounds, which is important in designing potent insecticides. , In addition, four-membered fatty ring piperidine, an important chemical structure with ideal lipid solubility and permeability, has important applications in improving the solubility of drug molecules . In this work, we designed and synthesized a series of N -[((4-amino-1-piperidinyl)­(aryl)­methanone)­iminomethyl]- N ′-methylurea compounds using lipophilic piperidine as a bridge connecting the planar structures and the pharmacophore N -methylcarbamoylguanidino (Figure ).…”