Biological evaluation of some octanoyl derivatives of methyl 4,6-O-cyclohexylidene-&amp;alpha;-D-glucopyranoside

Kabir, A. K. M. S.; Kawsar, Sarkar M. A.; Bhuiyan, M. M. H.; Rahman, Safiqur; Banu, B. Haseena

doi:10.3329/cujbs.v3i1.13406

Cited by 16 publications

(25 citation statements)

References 5 publications

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“…The presence of decanoyl and lauroyl group made the test chemicals very effective towards the growth of both Gram-positive and Gram-negative bacteria. The test chemicals containing octanoyl, decanoyl, lauroyl and benzenesulphonyl group were found to show very high antifungal activity which was in accordance with our previous work [27][28][29][30]. So these compounds may be targeted for future studies for their usage as broad spectrum antibiotics.…”

Section: Assessment Of Antimicrobial Effectssupporting

confidence: 71%

“…It also known that if an active nucleus is linked to another active nucleus, the resulting molecule may possess greater potential for biological activity [11]. Results of an ongoing our research project on selective acylation of carbohydrates [13][14][15][16][17] and also evaluation of microbial activities [18][19][20][21] reveal that in many cases the combination of two or more heteroaromatic nuclei and acyl groups enhances the biological activity manifold than its parent nucleus [22,23].…”

Section: Introductionmentioning

confidence: 99%

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Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Kawsar

Mymona

Asma

et al. 2015

ILCPA

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ABSTRACT.This study was carried out to regioselective myristoylation of methyl α-Dglucopyranoside (1) using the direct acylation method gave the corresponding methyl 6-Omyristoyl-α-D-glucopyranoside (2) in fair yield. A number of 2,3,4-tri-O-acyl derivatives (3-15) of this 6-O-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The reaction conditions are reasonably simple and yields were very good. The structures of the title compounds (2-15) were established by using analytical, physicochemical techniques and spectroscopic data (IR and 1 H-NMR). All the synthesized compounds were employed as test chemicals for in vitro antimicrobial functionality test against Gram-positive Bacillus subtilis, Staphylococcus aureus, Gram-negative Escherichia coli, Pseudomonas aeruginosa bacteria and plant pathogenic fungi Aspergillus niger and Candida albicans. For comparative studies, antimicrobial activity of standard antibiotics, Ampicillin and Nystatin were also carried out against these microorganisms. The study revealed that the tested samples exhibited moderate to good antibacterial and antifungal activities. It was also observed that the test substances were more effective against fungal phytopathogens than those of the human bacterial strains. Encouragingly, a number of tested chemicals showed nearest antibacterial and antifungal activities with the standard antibiotics employed.

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Section: Assessment Of Antimicrobial Effectssupporting

confidence: 71%

Section: Introductionmentioning

confidence: 99%

Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Kawsar

Mymona

Asma

et al. 2015

ILCPA

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“…The inhibitions of growth of bacteria were very remarkable in many cases which was in conformity with our previous work [32]- [35]. Of the test chemicals 6, 8, 9, and 12 were very effective towards the inhibition of growth of maximum Gram-negative bacterial strains used.…”

Section: Antibacterial Activitiessupporting

confidence: 65%

Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities

Kawsar¹,

Ara²,

Uddin³

et al. 2015

IJOC

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A new N-acetylsulfanilylation series of uridine have been synthesized in good yield using direct acylation method and afforded the 5'-O-N-acetylsulfanilyluridine. In order to obtain newer products, the 5'-O-N-acetylsulfanilyluridine derivative was further transformed to a series of 2',3'-di-Oacyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were confirmed on the basis of their FTIR, 1 H-NMR spectroscopy, physicochemical properties and elemental analysis. All the synthesized uridine derivatives were tested for their in vitro antibacterial activity against six human pathogenic bacterial strains and for comparison standard antibiotic Ampicillin was also determined. The study revealed that the selectively acylated derivatives 5'-O-N-acetylsulfanilyl-2',3'-di-O-lauroyluridine and 5'-O-N-acetylsulfanilyl-2',3'-di-O-pivaloyluridine showed highest inhibition against Staphylococcus aureus and Bacillus cereus, respectively. We also observed that the introduction of hexanoyl, decanoyl, lauroyl, myristoyl and pivaloyl groups, the antibacterial functionality of the compound uridine increases. Another noteworthy observation was that the uridine derivatives * Corresponding author. S. M. A. Kawsar et al. 233were found comparatively more effective against Gram-positive microorganisms than those of Gram-negative microorganisms. In addition, the test chemicals were also tested for cytotoxicity by brine shrimp lethality bioassay and compounds showed different rate mortality with different concentrations.

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“…From our previous works (Kawsar et al, 2013a(Kawsar et al, , 2015Kabir et al, 2008Kabir et al, , 2009, it also observed that in many cases the combination of two or more acyl substituents in a single molecular framework enhances the biological profile manifold than their parent nuclei (Kabir et al, 2004(Kabir et al, , 2005aKawsar et al, 2012a). Encouraged by our own findings and also literature reports, it synthesized a series of methyl α-D-glucopyranoside (1) derivatives ( Fig.…”

Section: Introductionmentioning

confidence: 92%

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Kawsar¹,

Uddin²,

Nishat³

et al. 2015

Current Research in Chemistry

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A novel regioselective benzenesulphonylation and N-acetylsulfanilylation series of methyl α-D-glucopyranoside derivative (1) has been carried out by direct method and afforded the 6-O-benzenesulfonyl derivative (2) and 6-O-N-acetylsulfanilyl derivative (7) in an excellent yields. In order to obtain newer products, the 6-O-glucopyranoside derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives (3-6 and 8-11) containing a wide variety of functionalities in a single molecular framework. The structures of the newly synthesized compounds were elucidated with the aid of FTIR, 1 H-NMR spectroscopy and elemental analysis. All the synthesized compounds were also tested for their antibacterial activity against some human pathogenic bacterial microorganisms. For comparative studies, antibacterial activity of standard antibiotics, ampicillin was also carried out against these microorganisms. The study revealed that the acylated products exhibit moderate to good antimicrobial activities. It was interesting to observe that the selected compounds were more sensitive against gram-negative bacteria than that of the gram-positive bacterial strains. We carried out the antibacterial activities of the tested chemicals in vitro. In vivo screening studies of the tested compounds showing promising results will be the subject of our future investigation.

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Biological evaluation of some octanoyl derivatives of methyl 4,6-O-cyclohexylidene-α-D-glucopyranoside

Cited by 16 publications

References 5 publications

Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

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