Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives (original) (raw)
Related papers
Antimicrobial evaluation of methyl 4-O-Acetyl-α-L-Rhamnopyranoside derivatives
Chittagong University Journal of Biological Sciences, 2013
A number of 2,3-di-O-acyl derivatives (6-11) of methyl 4-O-acetyl-a-Lrhamnopyranoside (5) obtained by using various acylating agents were screened for in vitro antifungal activity against four plant pathogenic fungi, viz., Alternaria alternata, Curvularia lunata. Fusarium equiseti and Macrophomina phaseolina. These compounds were also screened for in vitro antibacterial activity against ten human pathogenic bacteria, viz., Bacillus subtilis, Bacillus cereus, Bacillus megaterium, Staphylococcus aureus, Escherichia coli, INABA ET (Vibrio), Pseudomonas species, Salmonella paratyphi, Shigella dysenteriae and Salmonella typhi. The study reveal that these 4-O-acetyl-?-L-rhamnopyranoside derivatives are more prone towards antifungal activities than that of antibacterial activities. DOI: http://dx.doi.org/10.3329/cujbs.v3i1.13404 The Chittagong Univ. J. B. Sci.,Vol. 3(1&2):33-43, 2008
PASS Predication, Antiviral, in vitro Antimicrobial, and ADMET Studies of Rhamnopyranoside Esters
Medical research archives, 2020
Sugar derived esters (SEs) with potential antimicrobial activity were found to be a better choice to solve the multidrug resistant (MDR) pathogens due to improved antimicrobial efficacy, biodegradability, non-toxic, and non-allergic properties. In this context, a series of benzyl -Lrhamnopyranoside esters with different chain length (C2-C18) were employed for PASS predication, antiviral, and in vitro antimicrobial activity test. The in vitro antimicrobial tests against four bacterial, and four fungal pathogens along with PASS predication indicated that these sugar esters acted as better antifungals as compared to antibacterial functionality. The study revealed that the incorporation of octanoyl (C8) and lauroyl (C12) group(s) at C-3 position of rhamnopyranoside possessed promising antimicrobial, and anti-carcinogenic potentiality with good pharmacokinetic (pkCSM), and drug likeness properties. Also, attachment of multiple ester groups enhanced various drug likeness, and medicinal chemistry friendliness conditions. Overall, the present findings might be useful for the development of rhamnopyranoside based novel MDR antimicrobial drugs.
Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents
Current Chemistry Letters, 2017
Benzyl -L-rhamnopyranoside, prepared by both conventional and microwave assisted glycosidation techniques, was converted into benzyl 2,3-O-isopropylidene-α-Lrhamnopyranoside which after lauroylation followed by removal of isopropylidene group gave the benzyl 4-O-lauroyl-α-L-rhamnopyranoside in good yield. Several derivatives of benzyl 4-O-lauroyl-α-L-rhamnopyranoside were prepared and assessed in vitro for their antimicrobial activity against ten human pathogenic bacteria and seven fungi. The structure activity relationship (SAR) study revealed that incorporation of 4-O-lauroyl group in rhamnopyranoside frame work along with 2,3-di-O-acyl group increased the antifungal potentiality of the rhamnopyranosides.
In Silico Biological Profile Prediction of Some Selectively Synthesized Acyl Rhamnopyranosides
Journal of Scientific Research, 2021
Over the past several decades significant biological activities including brains protective and antimicrobial activities have made sugar esters (SEs) as a topic of great interest. In this context, unimolar 3-chlorobenzoylation of methyl α-L-rhamnopyranoside (4) using dibutyltin oxide method regioselectively furnished only the 3-O-substitution product 5 in excellent yield. The reaction proceeded via the formation of a cyclic 2,3-Odibutylstannylene intermediate where equatorial hydroxyl group is activated by the tin atom leading to the formation of product 5 only. To get biologically important rhamnopyranoside esters chlorobenzoate 5 was further converted into three newer 2,4-di-O-acyl products 6-9 with other acylating agents using direct acylation method. Prediction of activity spectra for substances (PASS) indicated that these rhamnopyranoside esters have many promising biological profiles including CYP2H substrate, membrane permeability inhibitor and better antifungal activities. Additionally, ADMET and drug likeness properties of SEs 5-8 were predicted and discussed.
Regioselective Synthesis of Some Rhamnopyranoside Esters for PASS Predication, and ADMET Studies
Journal of the Turkish Chemical Society Section A: Chemistry, 2021
Notable biological activities including brains protective activities have made carbohydrate esters as a topic of great interest over the past several decades. In this context, unimolecular treatment of methyl α-L-rhamnopyranoside with dibutyltin oxide gave the corresponding 2,3-O-(dibutylstannylene) derivative which was then allowed to react with 3-chlorobenzoyl chloride. The reaction regioselectively furnished the 3-O-substitution product in excellent yield. To get newer rhamnopyranoside esters chlorobenzoate was further converted into four 2,4-di-O-substituted products with other acylating agents using direct acylation technique. Moreover, thermodynamic properties indicated that these sugar esters (SEs) possess better stability, suitable polar nature and higher binding affinity than the non-ester rhamnopyranoside. Prediction of Activity Spectra for Substances (PASS) predication showed that these SEs should be more potent against fungal pathogens than the bacterial organisms. With these encouraging results absorption, distribution, metabolism, excretion, and toxicity (ADMET) and drug-likeness properties of the SEs are also discussed.
Molecules
The most widely used and accessible monosaccharides have a number of stereogenic centers that have been hydroxylated and are challenging to chemically separate. As a result, the task of regioselective derivatization of such structures is particularly difficult. Considering this fact and to get novel rhamnopyranoside-based esters, DMAP-catalyzed di-O-stearoylation of methyl α-l-rhamnopyranoside (3) produced a mixture of 2,3-di-O- (4) and 3,4-di-O-stearates (5) (ratio 2:3) indicating the reactivity of the hydroxylated stereogenic centers of rhamnopyranoside as 3-OH > 4-OH > 2-OH. To get novel biologically active rhamnose esters, di-O-stearates 4 and 5 were converted into six 4-O- and 2-O-esters 6–11, which were fully characterized by FT-IR, 1H, and 13C NMR spectral techniques. In vitro antimicrobial assays revealed that fully esterified rhamnopyranosides 6–11 with maximum lipophilic character showed better antifungal susceptibility than antibacterial activity. These experimental...
Hacettepe Journal of Biology and Chemistry, 2015
B u çalışmada, metil 6-O-sinamoil-α-D-glukopiranozid türevlerinin yeni bir serisi, piridinde çeşitli açilleyici ajanlarla, metil α-D-glukopiranozid (1) tepkimesi ile-5 o C'da sentezlendi. Bu amaçla ilk olarak metil α-D-glukopiranosid in seçici sinamalasyonu, doğrudan asilasyon yöntemi ile gerçekleştirildi ve iyi bir verimle metil 6-O-sinamoil-α-D-glukopiranozid elde edildi. İkinci olarak, antimikrobiyal tarama çalışmaları için yeni ürünler elde etmek amacıyla, 6 sinamoil türevleri tek bir molekül çerçevesinde 2,3,4-triO -asil türevlerini içeren geniş fonkisyonel gruplara dönüştürüldü. Yeni sentezlenen bileşiklerin yapıları IR ve NMR ile karakterize edildi. Tüm bileşikler, gıda zehirlenmesi ve disk difüzyon yöntemleri kullanılarak in vitro ortamda antibakteriyel ve antifungal aktiviteleri açısından değerlendirildi. Çalışmada metil 6-O-sinamoil-2,3,4-triO -dekanoilα-D-glukopiranosid bileşiği hem Gram (+) B. subtilise hem de Gram (-) P. aeruginosa mikroorganizmasına karşı yüksek inhibisyon etkisi gösterdi. Test bileşiği, metil 6-O-sinamoil-2,3,4-triO -lauroil-α-D-glukopiranosid A ya karşı maksimum misel büyüme inhibisyonu sergiledi. Açillenmiş türevlerin fungal hattına karşı olan etkisinin bakteriyel patojenlere göre daha yüksek olduğu bulundu. Bu, seçilen patojenlere karşı seçilmiş kimyasalların antimikrobiyal etkisini gösteren ilk raporudur.
Chemical Science
Reaction of 6-formylbenzopyranone derivative (1) with 2-(1-phenyl-ethylylidene) malononitrile led to formation of 7-hydroxy-chromen-6-yl-(1-phenyl-allylidene) malononitrile (2). Reaction of 2 with hydrazines led to formation of the corresponding aminopyrazole derivatives 3 and 4. While reaction of 2 with thiourea led to formation of 4,6-diaminopyrimidin-2-thione derivative 5. Hydrolysis of 2 with ammonium hydroxide afforded 2-cyano-5-(7-hydroxy-5-methoxy-2-methyl-4-oxo-4H-chromene-6-yl)-3-phenyl-penta-2,4-dienoic acidamide (6). The structures of the new compounds were confirmed on the basis of the elemental analysis and spectral data. All the synthesized products were evaluated for their antimicrobial activity.
Research in Pharmaceutical Sciences, 2009
Quantitative structure-activity relationship (QSAR) studies of a series of substituted 3-hydroxy-pyridine-4-ones and 3-hydroxy-pyran-4-ones as antibacterial and antifungal agents against a variety of microorganisms were performed. Multiple linear regression approach was used as variable selection method. The antimicrobial activities of these compounds against Staphylococcus aureus, Aspergilus niger and Candida albicans were subjected to QSAR analysis. The best QSAR models were achieved for the antimicrobial activity of the studied compounds against Staphylococcus aureus and Candida albicans Quantum, constitutional and geometrical parameters had important roles in the antimicrobial activity against Staphylococcus aureus. Geometrical, functional group and topological parameters of the compounds had important effect on the antimicrobial activity against Candida albicans. The equation describing this effect had a good statistical quality (R2=0.81, SE=0.14, Q2=0.73)
European Journal of Medicinal Chemistry, 2009
A series of Mannich bases of 2-alkyl-3-hydroxy-pyridine-4-ones, namely 2-alkyl-3-hydroxy-5-N-piperidylmethyl or N,N-dialkylaminomethyl pyridine-4-ones 9, 10 and 15–18, two derivatives of N-aryl-2-methyl-3-hydroxy-pyridine-4-ones 19, 20 and two N-alkyl derivatives of maltol, 21 and 22 were prepared. They were screened for their antibacterial and antifungal activities against a variety of microorganisms using micro plate Alamar Blue® assay (MABA) method. Multiple linear regressions (MLR) analysis was performed for the synthesized compounds as well as a series of pyridinone and pyranone derivatives 23–43 which have been synthesized and evaluated for antimicrobial activity by other researchers previously. Studied compounds showed a better quantitative structure–activity relationship (QSAR) model for the antimicrobial activity against Candida albicans and Staphylococcus aureus in comparison with other tested microorganisms.