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Int. J. Mol. Sci. 2016, 17(9), 1412; doi:10.3390/ijms17091412

Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives

1
Organic Research Laboratory, Department of Chemistry, University of Chittagong, Chittagong 4331, Bangladesh
2
Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Institute of Postgraduate Studies Building, Kuala Lumpur 50603, Malaysia
3
Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, Malaysia
4
Division of Human Biology, School of Medicine, International Medical University, Kuala Lumpur 57000, Malaysia
5
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
*
Authors to whom correspondence should be addressed.
Academic Editor: Ge Zhang
Received: 24 June 2016 / Revised: 3 August 2016 / Accepted: 16 August 2016 / Published: 27 August 2016
(This article belongs to the Special Issue Translational Molecular Medicine & Molecular Drug Discovery)
View Full-Text   |   Download PDF [816 KB, uploaded 27 August 2016]   |  

Abstract

Benzyl α-l-rhamnopyranoside 4, obtained by both conventional and microwave assisted glycosidation techniques, was subjected to 2,3-O-isopropylidene protection to yield compound 5 which on benzoylation and subsequent deprotection of isopropylidene group gave the desired 4-O-benzoylrhamnopyranoside 7 in reasonable yield. Di-O-acetyl derivative of benzoate 7 was prepared to get newer rhamnopyranoside. The structure activity relationship (SAR) of the designed compounds was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antimicrobial activities verified the predictions obtained by the PASS software. Protected rhamnopyranosides 5 and 6 exhibited slight distortion from regular 1C4 conformation, probably due to the fusion of pyranose and isopropylidene ring. Synthesized rhamnopyranosides 48 were employed as test chemicals for in vitro antimicrobial evaluation against eight human pathogenic bacteria and two fungi. Antimicrobial and SAR study showed that the rhamnopyranosides were prone against fungal organisms as compared to that of the bacterial pathogens. Interestingly, PASS prediction of the rhamnopyranoside derivatives 48 were 0.49 < Pa < 0.60 (where Pa is probability ‘to be active’) as antibacterial and 0.65 < Pa < 0.73 as antifungal activities, which showed significant agreement with experimental data, suggesting rhamnopyranoside derivatives 48 were more active against pathogenic fungi as compared to human pathogenic bacteria thus, there is a more than 50% chance that the rhamnopyranoside derivative structures 48 have not been reported with antimicrobial activity, making it a possible valuable lead compound. View Full-Text
Keywords: L-rhamnose; benzyl α-L-rhamnopyranoside; benzoylation; prediction of activity spectra for substances (PASS); structure activity relationship; antimicrobial agents L-rhamnose; benzyl α-L-rhamnopyranoside; benzoylation; prediction of activity spectra for substances (PASS); structure activity relationship; antimicrobial agents
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Matin, M.M.; Nath, A.R.; Saad, O.; Bhuiyan, M.M.H.; Kadir, F.A.; Abd Hamid, S.B.; Alhadi, A.A.; Ali, M.E.; Yehye, W.A. Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives. Int. J. Mol. Sci. 2016, 17, 1412.

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