Glucopyranoside Dipentanoyl Esters: Synthesis, PASS Predication, Antimicrobial and <i>In Silico</i> ADMET Studies

Abstract

Dimolar pentanoylation of methyl α-D-glucopyranoside using direct method furnished the 2,6-di-O-pentanoate indicating regioselectivity at C-6 and C-2 positions. To develop glucopyranoside based potential antimicrobial agents, 2,6-di-O-pentanoate was further converted into eight newer 3,4-di-O-acyl esters reasonably in good yields. Both prediction of activity spectra for substances (PASS) and in vitro antimicrobial activity test established them as better antifungals than antibacterials. PASS predication also indicated that these sugar esters (SEs) are more potent as anticarcinogenic agents than as antioxidant agents. Structure activity relationship along with in silico ADMET studies clearly indicated that combination of pentanoyl (C5) and lauroyl (C12) in the glucopyranoside framework could be a potential antifungal agent especially against Macrophomina phaseolina.

<i>In Silico</i> Biological Profile Prediction of Some Selectively Synthesized Acyl Rhamnopyranosides

“…In silico prediction of drug bio-profiles provides a non-laborious and less expensive way to find novel drug candidates, and also shed light on the hidden pharmacological potential of the launched drugs [45]. Considering these aspects, we have used web-based PASS (Prediction of Activity Spectra for Substances; http://www.way2drug.com/passonline/) for the prediction of biological activities of the synthesized SEs [45][46][47]. It is well known program which can predict/calculate a plethora of biological activities with 90% accuracy.…”

“…Web based PASS (Prediction of Activity Spectra for Substances; http://www.way2drug.com/passonline/) [45][46][47] predication selective results are presented in Table 2. The data indicated that these rhamnopyranoside esters 5-8 could be more active against fungal pathogens (0.66 < Pa < 0.70) as compared to bacterial organisms (0.53 < Pa < 0.54).…”

Chemical Reactivity Descriptors and Molecular Docking Studies of Octyl 6-O-hexanoyl-β-D-glucopyranosides

“…Hexanoyl glucosides 2-7 of n-octyl β-D-glucopyranoside (1) were selected for the present study (Figure 2). These compounds were synthesized and duly characterized previously by our group [51] using the direct acylation technique [52][53][54][55][56].…”

Synthesis and DFT Studies of Glucopyranoside Dipentanoyl Esters

“…Also, variable antimicrobial results are reported by different researchers (Petrova et al, 2018;Kabir and Matin, 1994), and there are few reports on their molecular docking with different essential proteins (Ye and Hayes, 2017). Considering biological and synthetic importance of glucose molecule, several 2,6-di-O-pentanoyl esters were synthesized from methyl α-D-glucopyranoside (1), and DFT based thermodynamic and docking studies were conducted (Matin et al, 2021a). The additional part of the series (2-6) are reported and discussed herein.…”