Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents

Matin, Mohammed Mahbubul; Bhuiyan, M. M. H.; Azad, Abul K.M.S.; Akther, Nishat

doi:10.5267/j.ccl.2016.10.001

Cited by 16 publications

(13 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, the two major challenges with CFA ester syntheses are- (i) the presence of several 2° hydroxyl groups of almost similar reactivity, mostly affecting functionalization (esterification) step leading to a mono-, di-, and polyesters [ 20 ], and (ii) the tremendous variation (variety) of carbohydrate structures. Accordingly, various methods have been attempted and reported in the last couple of decades for selective esterification (acylation) [ [21] , [22] , [23] , [24] , [25] , [26] , [27] , [28] , [29] , [30] , [31] , [32] ]. All the methods and/or strategies described were successful to some extents, however, suffered from numerous shortcomings, i.e.…”

Section: Introductionmentioning

confidence: 99%

Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies

Matin

Chakraborty

Alam

et al. 2020

Carbohydrate Research

Self Cite

View full text Add to dashboard Cite

Direct unimolar one-step valeroylation of methyl α- d -mannopyranoside (MDM) furnished mainly 6- O -valeroate. However, similar reaction catalyzed by DMAP resulted 3,6-di- O -valeroate (21%) and 6- O -valeroate (47%) indicating reactivity sequence as 6-OH>3-OH>2-OH,4-OH. To get potential antimicrobial agents, 6- O -valeroate was converted into four 2,3,4-di- O -acyl esters, and 3,6-di- O -valeroate was converted into 2,4-di- O -acetate. Direct tetra- O -valeroylation of MDM gave a mixture of 2,3,4,6-tetra- O -valeroate and 2,3,6-tri- O -valeroate indicating that the C2–OH is more reactive than the equatorial C4–OH. The activity spectra analysis along with in vitro antimicrobial evaluation clearly indicated that these novel MDM esters had better antifungal activities over antibacterial agents. In this connection, molecular docking indicated that these MDM esters acted as competitive inhibitors of sterol 14α-demethylase (CYP51), an essential enzyme for clinical target to cure several infectious diseases. Furthermore, pharmacokinetic studies revealed that these MDM esters may be worth considering as potent candidates for oral and topical administration. Structure activity relationship (SAR) affirmed that saturated valeric chain (C5) in combination with caprylic (C8) chains was more promising CYP51 inhibitor over conventional antifungal antibiotics.

show abstract

Section: Introductionmentioning

confidence: 99%

Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies

Matin

Chakraborty

Alam

et al. 2020

Carbohydrate Research

Self Cite

View full text Add to dashboard Cite

show abstract

“…These alcoholic groups compete during functionalization (esterification) step leading to a mono-, di-, and polyesters [17]. Different type of methods have so far been developed in the last couple of decades and employed successfully for selective esterification (acylation) such as protection-deprotection technique [18,19], organotin [20,21] and other catalyst mediated technique [22], microwave (MW) assisted method [23], enzyme catalyzed method [24] and direct method [25][26][27]. Some of them have many shortcomings such as increase the number of steps, tedious, expensive and generally decrease the overall yield.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

View full text Add to dashboard Cite

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.

show abstract

“…SEs are also used as synthetic intermediates of various natural products synthesis due to the presence of multifunctional groups, [15][16][17], and hence, they contribute in the design and development of new drugs [18,19]. Although various methods were reported for SEs synthesis [20][21][22][23][24][25] the presence of several similar reactive 2° hydroxyl groups with tremendous structural variation made selective acylation (esterification) challenging [26]. Most of the synthetic methods have both advantages and shortcomings like complex processes of multiple steps, tedious, expensive, low selectivity and gave extremely low yield [27][28].…”

Section: Introductionmentioning

confidence: 99%

<i>In Silico</i> Biological Profile Prediction of Some Selectively Synthesized Acyl Rhamnopyranosides

Chowdhury

Bhattacharjee

2021

J. Sci. Res.

View full text Add to dashboard Cite

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-O-dibutylstannylene 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.

show abstract

Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents

Cited by 16 publications

References 18 publications

Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies

Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies

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

<i>In Silico</i> Biological Profile Prediction of Some Selectively Synthesized Acyl Rhamnopyranosides

Contact Info

Product

Resources

About