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

Authors

  • M. M. Matin Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, University of Chittagong https://orcid.org/0000-0003-4965-2280
  • S. A. Chowdhury Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, University of Chittagong, Chattogram 4331, Bangladesh
  • M. M. H. Bhuiyan Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, University of Chittagong, Chattogram 4331, Bangladesh
  • S. M. A. Kawsar Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, University of Chittagong, Chattogram 4331, Bangladesh
  • M. A. Alam Department of Chemistry and Biological Sciences, Iwate University, Morioka, Japan

DOI:

https://doi.org/10.3329/jsr.v13i1.48147

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.

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Published

2021-01-01

How to Cite

Matin, M. M., Chowdhury, S. A., Bhuiyan, M. M. H., Kawsar, S. M. A., & Alam, M. A. (2021). Glucopyranoside Dipentanoyl Esters: Synthesis, PASS Predication, Antimicrobial and <i>In Silico</i> ADMET Studies. Journal of Scientific Research, 13(1), 221–235. https://doi.org/10.3329/jsr.v13i1.48147

Issue

Vol. 13 No. 1 (2021)

Section

Section B: Chemical and Biological Sciences

License

© Journal of Scientific Research

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