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Title

Glucopyranoside Dipentanoyl Esters: Synthesis, PASS Predication, Antimicrobial and In Silico ADMET Studies.

Authors

Matin, M. M.; Chowdhury, S. A.; Bhuiyan, M. M. H.; Kawsar, S. M. A.; Alam, M. A.

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.

Subjects

GLUCOPYRANOSIDE; ESTERS; STRUCTURE-activity relationships; ANTICARCINOGENIC agents; ANTIFUNGAL agents; MACROPHOMINA phaseolina

Publication

Journal of Scientific Research, 2021, Vol 13, Issue 1, p221

ISSN

2070-0237

Publication type

Academic Journal

DOI

10.3329/jsr.v13i1.48147

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