Efficient Synthetic Technique, PASS Predication, and ADMET Studies of Acylated n-Octyl Glucopyranosides

Ali, Mohammad; Karim, Md. Hasanul; Matin, Mohammed Mahbubul

doi:10.33736/jaspe.2823.2021

Cited by 6 publications

(6 citation statements)

References 31 publications

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“…Some thermodynamic properties like electronic energy (EE), enthalpy, Gibb's free energy (GFE), entropy and dipole moment (DM) of all the rhamnopyranosides 3-9a-d are predicted from their DFT optimized structures (Table 3). With the increase of molecular size and atoms their EE increased as usual [53].…”

Section: Thermodynamic Propertiesmentioning

confidence: 79%

The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study

Islam

Rahman

Matin

2021

Turkish Computational and Theoretical Chemistry

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Carbohydrate fatty acid (CFA) esters especially rhamnopyranoside esters having both the hydrophilic and lipophilic nature showed broader applications including anticancer activities. It was reported that appropriate conformation is needed for better activities and conformational distortion reduced antimicrobial functionality. In this context, two different esters series of benzyl α-L-rhamnopyranosides, one with 2,3-O-acetonide group and the other one without acetonide group, were subjected for the density functional theory (DFT) optimization. The optimized structures with 2,3-O-acetonide rhamnopyranoside clearly showed distortion from the regular 1C4 chair conformation while rhamnopyranoside esters without 2,3-O-acetonide functionality exhibited almost regular 1C4 chair conformation. Also, the number and position of acyl group(s) present in the benzyl rhamnopyranoside imposes a small effect on their pyranose chair conformation. Thermodynamic properties including frontier molecular orbitals (FMO) and molecular electrostatic potential (MEP) of both the series of rhamnopyranosides are also discussed which indicated that 4-O-acyl rhamnopyranosides are more reactive than the 3-O-acyl analogues.

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Section: Thermodynamic Propertiesmentioning

confidence: 79%

The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study

Islam

Rahman

Matin

2021

Turkish Computational and Theoretical Chemistry

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“…The optimized structures were used for several thermodynamic properties prediction employing GaussView and WebMD [23]. Molecular orbitals like HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) possess salient features for their inherent reactivity.…”

Section: Thermodynamic Properties Molecular Orbitals and Chemical Rea...mentioning

confidence: 99%

“…The sugar part i.e. glucose part generally contributes to increased water solubility [15][16][17][18][19][20], biodegradability [21][22][23] and bioactivities [24][25][26][27][28][29] of the attached remaining part(s). For example, the addition of monosaccharide units as in amphotericin and/or nystatin increases their bioactivity and reduces their side effects [30].…”

Section: Introductionmentioning

confidence: 99%

In Silico Investigation of Some Glucose-Aspirin as COX Inhibitor

Chowdhury

Anisa²,

Bhattacharjee³

et al. 2022

J. Appl. Sci. Process Eng.

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Monosaccharide derived glucose-aspirin (GA) can be prepared by conjugation between glucose and aspirin (ASA). The GA is reported to show higher analgesic and anti-inflammatory properties than ASA itself. In this perspective, six GAs which are composed of β-D-glucopyranose, ASA and acetyl groups are considered for the present investigations. The glucose unit in these GAs possesses regular chair conformation with slightly lower dipole moments. Molecular orbitals indicated a higher HOMO-LUMO gap of the molecules. All GAs showed more prone to electrophilic interactions than aspirin. Overall, glucose-aspirin esters are found to have better non-steroidal anti-inflammatory properties than the original aspirin. These GAs are better inhibitors of cyclooxygenase-2 (COX2, 5f19) compared to cyclooxygenase-1 (COX1, 6y3c) indicating that these GAs are potential drug candidates for COX2 related inflammation. Additionally, aspirinyl group at C-6 or C-3 position of the glucopyranose unit is found more suitable for anti-inflammatory activities as compared to C-4 position.

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“…Chemical absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiling aids in reducing potential dangers throughout clinical development [54]. Scientists are aware that ADMET profiling is required to identify whether or not a molecule is suitable to advance to the clinical stage because drug development failures might be caused by efficacy or safety difficulties [55,56]. Utilizing the pkCSM tool (http://biosig.unimelb.edu.au), in silico ADMET was calculated for the current experiment [57].…”

Section: Admet Calculationmentioning

confidence: 99%

Naturally Occurring Rhamnopyranosides as Anticancer Agents: Molecular Docking and ADMET Study

Islam

Sultan²,

Hossain³

et al. 2022

J. Appl. Sci. Process Eng.

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After heart disease, cancer continues to be the second most prevalent cause of death in the USA. Several chemotherapeutic treatments (drugs) are available for cancer that use powerful chemicals to kill the body's rapidly proliferating cells. However, recent research disclosed that many clinically viable anticancer drugs have been developed with the help of chemicals originating from plants. A number of phytochemicals isolated from plants possess rhamnopyranoses and some of them are acyl rhamnopyranoses. Encouragingly, such compounds were reported for their cell proliferation and migration inhibition activities against invasive human triple-negative breast cancer cells. In this study, four naturally occurring rhamnopyranose esters were checked against three cancer-related proteins (PDB IDs: 3TJM, 4OAR, and 5FGK) via molecular docking. Rhamnose compounds 3-6 showed better binding energy compared to the related standard drugs in use in the hospitals. Compound 6 was found highly potential against all the proteins (-8.5 to -11.3 kcal/mol). ADMET studies have also been discussed in this respect. This study indicated that natural rhamnopyranose esters could be used to stop the spreading of cancer cells like other reported sugar fatty acid esters (SFAEs).

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Efficient Synthetic Technique, PASS Predication, and ADMET Studies of Acylated n-Octyl Glucopyranosides

Cited by 6 publications

References 31 publications

The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study

The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study

In Silico Investigation of Some Glucose-Aspirin as COX Inhibitor

Naturally Occurring Rhamnopyranosides as Anticancer Agents: Molecular Docking and ADMET Study

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