Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol

Majdi M. Bkhaitan; Mohammed Alarjah; Agha Zeeshan Mirza; Ashraf N. Abdalla; Hamdi M. El‐Said; Hani S. Faidah

doi:10.1111/cbdd.13366

journal article Aug 05, 2018

Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol

Majdi M. Bkhaitan

Mohammed Alarjah Agha Zeeshan Mirza Ashraf N. Abdalla

Hamdi M. El‐Said Hani S. Faidah

Chemical Biology & Drug Design Vol. 92 No. 6 pp. 1954-1962 · Wiley

View at Publisher Save 10.1111/cbdd.13366

Abstract

AbstractTwo series of metronidazole derivatives (ester derivatives and ether derivatives) were prepared reacting metronidazole and its acetic acid oxidized form with menthol, thymol, carvacrol, and eugenol. Both series of compounds were tested in vitro against two strains of Helicobacter pylori (the ATCC 26695 and P12), and one strain of Clostridium (Clostridium perfringens). Most of the prepared compounds showed biological activity against the targeted bacteria. Compound 11 was highly active against all tested bacterial strains, especially against P12 with IC50 0.0011 μM/ml. Compound 6 was highly active against C. perfringens with MIC 0.0094 nM/ml. Viability test was conducted for compound 11 to test its selectivity for normal human fetal lung fibroblasts (MRC5), and it was found to be non‐toxic with IC50 more than 50 μM/ml.

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References

33

[1]

10.1007/s12272-015-0686-4

[2]

10.1017/s0031182017002025

[3]

10.1159/000481224

[4]

Understanding the mechanisms and drivers of antimicrobial resistance

Alison H Holmes, Luke S P Moore, Arnfinn Sundsfjord et al.

The Lancet 10.1016/s0140-6736(15)00473-0

[5]

Harrison U. PLoS ONE (2017)

[6]

10.4236/ojgas.2018.81003

[7]

10.1111/apt.13497

[8]

10.1016/s0378-4274(02)00039-5

[9]

10.1016/j.ejmech.2016.03.041

[10]

10.1016/j.bmc.2014.03.004

[11]

10.1016/j.ejmech.2015.06.019

[12]

Metronidazole containing pyrazole derivatives potently inhibit tyrosyl‐tRNA synthetase: design, synthesis, and biological evaluation

Long‐Wang Chen, Peng‐Fei Wang, Dan‐Jie Tang et al.

Chemical Biology & Drug Design 10.1111/cbdd.12793

[13]

10.2174/138955713804484686

[14]

Mechanisms of Antibacterial Action of Three Monoterpenes

Domenico Trombetta, Francesco Castelli, Maria Grazia Sarpietro et al.

Antimicrobial Agents and Chemotherapy 10.1128/aac.49.6.2474-2478.2005

[15]

Importance of hydrogen bonding and aromaticity indices in QSAR modeling of the antioxidative capacity of selected (poly)phenolic antioxidants

Svetlana Jeremić, Slavko Radenković, Milos Filipovic et al.

Journal of Molecular Graphics and Modelling 10.1016/j.jmgm.2017.01.011

[16]

10.1016/j.foodchem.2016.04.111

[17]

10.2174/138161208786404227

[18]

10.3797/scipharm.1004-18

[19]

Oyedemi S. O. Afr. J. Biotechnol. (2009)

[20]

10.1590/s0100-40422009000600020

[21]

10.1186/1476-0711-4-20

[22]

10.1016/j.ejmech.2012.08.030

[23]

10.1007/s00044-012-0016-z

[24]

10.1007/s00044-011-9689-y

[25]

10.1002/jhet.5570450343

[26]

Zeb A. Med. Chem. (Los Angeles) (2012)

[27]

10.1016/j.bmc.2009.09.018

[28]

10.1111/cbdd.12987

[29]

10.1016/j.ejmech.2005.11.001

[30]

10.1093/labmed/14.9.549

[31]

10.1093/jac/dkn090

[32]

10.1016/j.phytochem.2017.11.007

[33]

10.1016/j.micpath.2016.08.008

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References

Details

Published: Aug 05, 2018
Vol/Issue: 92(6)
Pages: 1954-1962
License: View

Authors

M

Majdi M. Bkhaitan

Department of Pharmaceutical Chemistry Faculty of Pharmacy Umm Al‐Qura University Makkah Saudi Arabia

M

Mohammed Alarjah

Department of Pharmaceutical Chemistry Faculty of Pharmacy Umm Al‐Qura University Makkah Saudi Arabia

A

Agha Zeeshan Mirza

Science and Technology Unit (STU) Umm Al‐Qura University Makkah Saudi Arabia

A

Ashraf N. Abdalla

Department of Pharmacology and Toxicology Faculty of Pharmacy Umm Al‐Qura University Makkah Saudi Arabia

H

Hamdi M. El‐Said

Department of Medical Microbiology Faculty of Medicine Umm Al‐Qura University Makkah Saudi Arabia

H

Hani S. Faidah

Department of Medical Microbiology Faculty of Medicine Umm Al‐Qura University Makkah Saudi Arabia

Funding

Umm Al-Qura University Award: 18‐Med‐1‐01‐0009

Cite This Article

Majdi M. Bkhaitan, Mohammed Alarjah, Agha Zeeshan Mirza, et al. (2018). Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol. Chemical Biology & Drug Design, 92(6), 1954-1962. https://doi.org/10.1111/cbdd.13366

Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol

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