Efficient Synthetic Technique, PASS Predication, and ADMET Studies of Acylated n-Octyl Glucopyranosides

Authors

  • Mohammad Ali Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chattogram, 4331, Bangladesh https://orcid.org/0000-0002-4751-5832
  • Md. Hasanul Karim Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chattogram, 4331, Bangladesh https://orcid.org/0000-0002-5786-8260
  • Mohammed Mahbubul Matin Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chattogram, 4331, Bangladesh https://orcid.org/0000-0003-4965-2280

DOI:

https://doi.org/10.33736/jaspe.2823.2021

Keywords:

n-Octyl β-D-glucopyranoside (OBG), Carbohydrate Fatty Acid (CFA) Esters (SEs), PASS Predication, ADMET, SwissADME.

Abstract

Direct dimolar pentanoylation of octyl β-D-glucopyranoside (OBG) in pyridine-chloroform solvent system furnished the corresponding 3,6-di-O-pentanoate in improved yield. The pentanoate was further converted into three 2,4-di-O-acyl esters to get novel octyl glucopyranosides. To explore medicinal probability of OBG-based esters all the synthesized compounds were subjected for in silico PASS (prediction of activity spectra for substances) predication and ADMET (absorption, distribution, metabolism, excretion, and toxicity) studies. Both the studies indicated that OBG derived carbohydrate fatty acid (CFA) esters are potential alternative for multidrug resistant (MDR) pathogens, especially for fungal infections.

References

Zheng, Y., Zheng, M., Ma, Z., Xin, B., Guo, R., & Xu, X. (2015). Sugar Fatty Acid Esters. In Polar Lipids: Biology, Chemistry, and Technology, pp 215-243, Elsevier B.V. https://doi.org/10.1016/B978-1-63067-044-3.50012-1

Abd-Elbary, A., El-Laithy, H. M., & Tadros, M. I. (2008). Sucrose stearate-based proniosome-derived niosomes for the nebulisable delivery of cromolyn sodium, International Journal of Pharmacy, Vol.357, 189-198. https://doi.org/10.1016/j.ijpharm.2008.01.056

Matin, M. M., Chakraborty, P., Alam, M. S., Islam, M. M., & Hanee, U. (2020). Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies, Carbohydrate Research, Vol.496, 108130. https://doi.org/10.1016/j.carres.2020.108130

Matin, M. M., Bhuiyan, M. M. H., Kabir, E., Sanaullah, A. F. M., Rahman, M. A., Hossain, M. E., & Uzzaman, M. (2019). Synthesis, characterization, ADMET, PASS predication, and antimicrobial study of 6-O-lauroyl mannopyranosides, Journal of Molecular Structure, Vol.1195, 189-197. https://doi.org/10.1016/j.molstruc.2019.05.102

Kabir, A. K. M. S., & Matin, M. M. (1998). Synthesis and characterization of some D-mannose derivatives, The Chittagong University Journal of Science, Vol.22, No.1, 105-110. ISSN: 1561-1167

Matin, M. M., Hasan, M. S., Uzzaman, M., Bhuiyan, M. M. H., Kibria, S. M., Hossain, M. E., & Roshid, M. H. O. (2020). Synthesis, spectroscopic characterization, molecular docking, and ADMET studies of mannopyranoside esters as antimicrobial agents, Journal of Molecular Structure, Vol.1222, 128821. https://doi.org/10.1016/j.molstruc.2020.128821

Chansanroj, K., & Betz, G. (2010). Sucrose esters with various hydrophilic-lipophilic properties: Novel controlled release agents for oral drug delivery matrix tablets prepared by direct compaction, Acta Biomaterialia, Vol.6, 3101-3109. https://doi.org/10.1016/j.actbio.2010.01.044

Matin, M. M., Ibrahim, M., & Rahman, M. S. (2008). Antimicrobial evaluation of methyl 4-O-acetyl-α-L-rhamnopyranoside derivatives, The Chittagong University Journal of Biological Sciences, Vol.3, No.1&2, 33-43. http://dx.doi.org/10.3329/cujbs.v3i1.13404

Matin, M. M., Bhattacharjee, S. C., Chakraborty, P., & Alam, M. S. (2019). Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters, Carbohydrate Research, Vol.485, 107812. https://doi.org/10.1016/j.carres.2019.107812

Matin, M. M., Uzzaman, M., Chowdhury, S. A., & Bhuiyan, M. M. H. (2020). In vitro antimicrobial, physicochemical, pharmacokinetics, and molecular docking studies of benzoyl uridine esters against SARS-CoV-2 main protease, Journal of Biomolecular Structure and Dynamics. https://doi.org/10.1080/07391102.2020.1850358

Matin, M. M. (2008). Synthesis of D-glucose derived oxetane: 1,2-O-isopropylidene-4-(S)-3-O,4-C-methylene-5-O-methanesulfonyl-α-L-threo-pento-1,4-furanose, Journal of Applied Sciences Research, Vo.4, No.11, 1478-1482. ISSN: 1816157X

Dhavale, D. D., & Matin, M. M. (2004). Selective sulfonylation of 4-C-hydroxymethyl-β-L-threo-pento-1,4-furanose: Synthesis of bicyclic diazasugars, Tetrahedron, Vol.60, No.19, 4275-4281. https://doi.org/10.1016/j.tet.2004.03.034

Matin, M. M. (2008). One step intramolecular cyclization of diol via mesylation: Efficient synthesis of sugar derived [1,4]oxazepanes, Journal of Bangladesh Chemical Society, Vol.21, No.2, 179-183. ISSN 1022-016X

Yuan, S. S., Li, M. L., Chen, J. S., Zhou, L., & Zhou, W. (2017). Application of mono- or disaccharides in drug targeting and efficacy, ChemMedChem, e 10.1002/cmdc.201700762. https://doi.org/10.1002/cmdc.201700762

Matin, M. M. (2004). Synthesis and study of glycosidase inhibitory activity of piperidine, pyrrolidine and bicyclic azasugars, PhD Thesis, University of Pune, India.

AlFindee, M.N., Zhang, Q., Subedi, Y. P., Shrestha, J. P., Kawasaki, Y., Grilley, M., Taemoto, J. Y., & Chang, C. W. T. (2018). One-step synthesis of carbohydrate esters as antibacterial and antifungal agents, Bioorganic and Medicinal Chemistry, Vol.26, 765-774. https://doi.org/10.1016/j.bmc.2017.12.038

Tolnia, G. L., Nilsson, U. J., & Olofsson, B. (2016). Efficient O‐functionalization of carbohydrates with electrophilic reagents, Angewandte Chemie International, Edition, Vol.55, 11226-11230. https://doi.org/10.1002/anie.201605999

Matin, M. M., Bhuiyan, M. M. H., Azad, A. K. M. S., & Akther, N. (2017). Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents, Current Chemistry Letters, Vol.6, No.1, 31-40. https://doi.org/10.5267/j.ccl.2016.10.001

Matin, M. M., Bhuiyan, M. M. H., Azad, A. K. M. S., & Rashid, M. H. O. (2015). Synthesis of 6-O-stearoyl-1,2-O-isopropylidene-α-D-gluco-furanose derivatives for antimicrobial evaluation, Journal of Physical Science, Vo.26, No.1, 1-12. ISSN: 2180-4230

Kabir, A. K. M. S., & Matin, M. M. (1994). Regioselective acylation of a derivative of L-rhamonse using the dibutyltin oxide method, Journal of the Bangladesh Chemical Society, Vol.7, No.1, 73-79. ISSN: 1022-016X

Kabir, A. K. M. S., & Matin, M. M. (1997). Regioselective monoacylation of a derivative of L-rhamnose, Journal of Bangladesh Academy of Sciences, Vol.21, No.1, 83-88. ISSN 0378-8121

Kiyoshima, K., Sakamoto, M., Ishikura, T., Fukagawa, Y., Yoshioka, T., Naganawa, H., Sawa, T., & Takeuchi, T. (1989). Application of dibutyltin oxide method to regioselective acylation and alkylation of tylosin at C-4'', Chemical and Pharmaceutical Bulletin, Vo.37, No.4, 861-865. https://doi.org/10.1248/cpb.37.861

Kabir, A. K. M. S., Matin, M. M., Bhuiyan, M. M. R., & Rahim, M. A. (2001). Synthesis and characterization of some acylated derivatives of D-mannose, The Chittagong University Journal of Science, Vo.25, No.1, 65-73. ISSN: 1561-1167

Kabir, A. K. M. S., Matin, M. M., Kawsar, S. M. A., & Anwar, M. N. (1998). Antibacterial activities of some selectively acylated uridine derivatives, The Chittagong University Journal of Science, Vol.22, No.2, 37-41. ISSN: 1561-1167

Matin, M. M., & M. Ibrahim (2010). Synthesis of some methyl 4-O-octanoyl-α-L-rhamnopyranoside derivatives, Journal of Applied Sciences Research, Vol.6, No.10, 1527-1532. ISSN: 1816-157X

Gumel, A. M., Annuar, M. S. M., Heidelberg, T., & Chisti, Y. (2011). Lipase Mediated synthesis of Sugar fatty acid esters, Process Biochemistry, Vol.46, 2079-2090. https://doi.org/10.1016/j.procbio.2011.07.021

Ortiz, Á. D-., Prieto, P., & de la Hoz, A. (2019). A critical overview on the effect of microwave irradiation in organic synthesis, The Chemical Record, Vol.19, No.1, 85-97. https://doi.org/10.1002/tcr.201800059

Kabir, A. K. M. S., Matin, M. M., & Uddin, M. R. (1998). Comparative studies on selective acylation of uridine using the dibutyltin oxide and direct methods, The Chittagong University Journal of Science, Vol.22, No.1, 97-103. ISSN: 1561-1167

Ren, D. B., Zhang, L., & Zhang, M. (2019). Progress on selective acylation of carbohydrate hydroxyl groups, Asian Journal of Organic Chemistry, Vol.8, 1813-1823. https://doi.org/10.1002/ajoc.201900400

Matin, M. M. (2006). Synthesis of some protected 6-O-acyl-galactopyranose derivatives for antibacterial evaluation, The Chittagong University Journal of Science, Vol.30, No.2, 59-65. ISSN: 1561-1167

Abronina, P. I., Malysheva, N. N., Zinin, A. I., Kolotyrkina, N. G., Stepanova, E. V., & Kononov, L. O. (2020). Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid, RSC Advances, Vol.10, 36836-36842. https://doi.org/10.1039/D0RA07360A

Matin, M. M., & Azad, A. K. M. S. (2006). Synthesis of some protected 6-O-acyl-galactopyranose derivatives, Journal of Applied Sciences Research, Vol.2, No.12, 1199-1202. ISSN: 1816157X

Matin, M. M., Bhuiyan, M. M. H., Hossain, M. M., & Roshid, M. H. O. (2015). Synthesis and comparative antibacterial studies of some benzylidene monosaccharide benzoates, Journal of the Turkish Chemical Society Section A: Chemistry, Vol.2, No.4, 12-21. https://doi.org/10.18596/jotcsa.83708

Kabir, A. K. M. S., & Matin, M. M. (1999). Antibacterial activities of some monosaccharide derivatives, The Chittagong University Journal of Science, Vol.23, No.2, 121-123. ISSN: 1561-1167

Kabir, A. K. M. S., Matin, M. M., & Bhuiyan, M. J. U. (1997). Regioselective monoacylation of methyl 4,6-O-benzylidene-α-D-glucopyranoside, Chittagong University Studies, Part II: Science, Vol.21, No.2, 33-38. ISSN: 1561-1167

Matin, M. M., & Chakraborty, P. (2020). Synthesis, spectral and DFT characterization, PASS predication, antimicrobial, and ADMET studies of some novel mannopyranoside esters, Journal of Applied Science & Process Engineering, Vol.7, No.2, 572-586. https://doi.org/10.33736/jaspe.2603.2020

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 in silico ADMET studies, Journal of Scientific Research, Vol.13, No.1, 221-235. http://dx.doi.org/10.3329/jsr.v13i1.48147

Murtazalieva, K. A., Druzhilovskiy, D. S., Goel, R. K., Sastry, G. N., & Poroikov, V. V. (2017). How good are publicly available web services that predict bioactivity profiles for drug repurposing?, SAR and QSAR in Environmental Research, Vol.28, No.10, 843-862. https://doi.org/10.1080/1062936X.2017.1399448

Matin, M. M., Nath, A. R., Saad, O., Bhuiyan, M. M. H., Kadir, F. A., Hamid, S. B. A., Alhadi, A. A., Ali, M. E., & Yehye, W.A. (2016). Synthesis, PASS-predication and in vitro antimicrobial activity of benzyl 4-O-benzoyl-α-L-rhamnopyranoside derivatives, International Journal of Molecular Sciences, Vol.17, No.9, 1412. https://doi.org/10.3390/ijms17091412

Chowdhury, S. A., Chakraborty, P., Kawsar, S. M. A., Bhuiyan, M. M. H., Matin, M. M. (2018). Regioselective acylation, PASS prediction and antimicrobial properties of some protected glucopyranosides, Journal of Bangladesh Chemical Society, Vol.30, No.1, 1-9. ISSN 1022-016X

Matin, M. M., Roshid, M. H. O., Bhattacharjee, S. C., & Azad, A. K. M. S. (2020). PASS predication, antiviral, in vitro antimicrobial, and ADMET studies of rhamnopyranoside esters, Medical Research Archives, Vol.8, No.7, 2165. https://doi.org/10.18103/mra.v8i7.2165

Han, Y., Zhang, J., Hu, C. Q., Zhang, X., Ma, B., & Zhang, P. (2019). In silico ADME and toxicity prediction of Ceftazidime and its impurities, Frontiers Pharmacology, Vol.10, 434. https://doi.org/10.3389/fphar.2019.00434

Rahim, A., Bhuiyan, M. M. H., & Matin, M. M. (2020). Microwave assisted efficient synthesis of some flavones for antimicrobial and ADMET studies, Journal of Scientific Research, Vol.12, No.4, 673-685. http://dx.doi.org/10.3329/jsr.v12i4.45523

Lohidakshan, K., Rajan, M., Ganesh, A., Paul, M., Jerin, J. (2018). Pass and Swiss ADME collaborated in silico docking approach to the synthesis of certain pyrazoline spacer compounds for dihydrofolate reductase inhibition and antimalarial activity, Bangladesh Journal of Pharmacology, Vol.13, 23-29. eISSN: 1991-0088

Dinesh, M., Deepika, S., Kumar, R. H., Selvaraj, C. I., & Roopan, S. M. (2017). Evaluation of octyl-β-D-glucopyranoside (OGP) for cytotoxic, hemolytic, thrombolytic, and antibacterial activity, Applied Biochemistry and Biotechnologr, Vol.185, No.4, 450-463. https://doi.org/10.1007/s12010-017-2661-7

Kabir, A. K. M. S., & Matin, M. M. (1996). Selective pivaloylation of some D-glucose derivatives, Chittagong University Studies, Part II: Science, Vol.20, No.2, 105-111. ISSN: 1561-1167

Matin, M. M. (2014). Synthesis and antimicrobial study of some methyl 4-O-palmitoyl-α-L-rhamnopyranoside derivatives, Orbital: The Electronic Journal of Chemistry, Vol.6, No.1, 20-28. https://doi.org/10.17807/orbital.v6i1.553

Kabir, A. K. M. S., Matin, M. M., Bhuiyan, M. M. R., Rahim, M. A., & Rahman, M. S. (2005). Biological evaluation of some monosaccharide derivatives International Journal of Agriculture and Biology, Vol.7, No.2, 218-221. ISSN 1814-9596

Matin, M. M., Bhuiyan, M. H., Hossain, M. M., & Roshid, M. H. O. (2015). Comparative antibacterial activities of some monosaccharide and disaccharide benzoates, Orbital: The Electronic Journal of Chemistry, Vol.7, No.2, 160-167. https://doi.org/10.17807/orbital.v7i2.699

Journal of Applied Science & Process Engineering, Volume 8, Number 1, 2021

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2021-04-30

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Ali, M., Karim, M. H., & Matin, M. M. (2021). Efficient Synthetic Technique, PASS Predication, and ADMET Studies of Acylated n-Octyl Glucopyranosides. Journal of Applied Science &Amp; Process Engineering, 8(1), 648–659. https://doi.org/10.33736/jaspe.2823.2021

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Vol. 8 No. 1 (2021): Journal of Applied Science & Process Engineering, Volume 8, Number 1, 2021

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