Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives
| Autor: | Abeer A. Alhadi, Sharifah Bee Abd Hamid, Amit R. Nath, Mohammad M. H. Bhuiyan, Md. Eaqub Ali, Farkaad A. Kadir, Wageeh A. Yehye, Omar Saad, Mohammed Mahbubul Matin |
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| Rok vydání: | 2016 |
| Předmět: |
0301 basic medicine
prediction of activity spectra for substances (PASS) Oligosaccharides antimicrobial agents medicine.disease_cause 01 natural sciences Rhamnose benzoylation lcsh:Chemistry chemistry.chemical_compound L-rhamnose benzyl α-L-rhamnopyranoside structure activity relationship Anti-Infective Agents lcsh:QH301-705.5 Spectroscopy biology General Medicine Antimicrobial Computer Science Applications Pyranose Carbohydrate Sequence l-rhamnose Lead compound Stereochemistry Microbial Sensitivity Tests Catalysis Article Inorganic Chemistry 03 medical and health sciences Structure-Activity Relationship medicine Structure–activity relationship Physical and Theoretical Chemistry Molecular Biology Bacteria 010405 organic chemistry Organic Chemistry Fungi Pathogenic bacteria biology.organism_classification 0104 chemical sciences 030104 developmental biology lcsh:Biology (General) lcsh:QD1-999 chemistry Yield (chemistry) benzyl α-l-rhamnopyranoside Software |
| Zdroj: | International Journal of Molecular Sciences International Journal of Molecular Sciences; Volume 17; Issue 9; Pages: 1412 International Journal of Molecular Sciences, Vol 17, Iss 9, p 1412 (2016) |
| ISSN: | 1422-0067 |
| Popis: | 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 4–8 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 4–8 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 4–8 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 4–8 have not been reported with antimicrobial activity, making it a possible valuable lead compound. |
| Databáze: | OpenAIRE |
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