Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol

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

doi:10.1111/cbdd.13366

Cited by 16 publications

(8 citation statements)

References 34 publications

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“…Among the first cluster of alkyloxy derivatives (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14), the MIC results demonstrated no or weak efficacy against all the strains as well as their parent compound, despite the presence of branched alkyl chains, unsaturations or specific functional groups (ketone, carboxylic acid, ethyl ester). Only three derivatives (3,9,12) with linear and increasing alkyl chains (Et, n-Pr, n-Bu) presented improved MIC values with respect to thymol against some clinical isolates (MIC/MBC = 16 µg/mL). Similar results were obtained for the aliphatic derivatives of carvacrol in our previous paper [15].…”

Section: Anti-helicobacter Pylori Activity and Structure-activity Relmentioning

confidence: 99%

“…In this context, novel compounds such as components of essential oils endowed with alternative mechanisms of action and the ability to disaggregate lipidic multilayer structures are strongly suggested [7]. More in detail, thymol derivatives have been proposed as inhibitors of CagA and VacA (cytotoxin-associated gene A and vacuolization cytotoxin) oncoproteins of Helicobacter pylori [8] and, recently, Bkhaitan et al also prepared a thymol-metronidazole ester hybrid and assessed its discrete anti-Helicobacter pylori activity and limited cytotoxicity on normal cell lines [9].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line

Sisto¹,

Carradori²,

Guglielmi³

et al. 2021

Molecules

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Following a similar approach on carvacrol-based derivatives, we investigated the synthesis and the microbiological screening against eight strains of H. pylori, and the cytotoxic activity against human gastric adenocarcinoma (AGS) cells of a new series of ether compounds based on the structure of thymol. Structural analysis comprehended elemental analysis and 1H/13C/19F NMR spectra. The analysis of structure–activity relationships within this molecular library of 38 structurally-related compounds reported that some chemical modifications of the OH group of thymol led to broad-spectrum growth inhibition on all isolates. Preferred substitutions were benzyl groups compared to alkyl chains, and the specific presence of functional groups at para position of the benzyl moiety such as 4-CN and 4-Ph endowed the most anti-H. pylori activity toward all the strains with minimum inhibitory concentration (MIC) values up to 4 µg/mL. Poly-substitution on the benzyl ring was not essential. Moreover, several compounds characterized by the lowest minimum inhibitory concentration/minimum bactericidal concentration (MIC/MBC) values against H. pylori were also tested in order to verify a cytotoxic effect against AGS cells with respect to 5-fluorouracil and carvacrol. Three derivatives can be considered as new lead compounds alternative to current therapy to manage H. pylori infection, preventing the occurrence of severe gastric diseases. The present work confirms the possibility to use natural compounds as templates for the medicinal semi-synthesis.

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Section: Anti-helicobacter Pylori Activity and Structure-activity Relmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line

Sisto¹,

Carradori²,

Guglielmi³

et al. 2021

Molecules

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show abstract

“…Both compounds demonstrated good activity against H. pylori strain. It is worth noting that the ether derivative ( 31 ) is more active than the ester ( Figure 8 ) [ 34 ].…”

Section: Monoterpene Monocyclic Derivativesmentioning

confidence: 99%

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

Zielińska-Błajet

Feder‐Kubis

2020

IJMS

217

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Monoterpenes, comprising hydrocarbons, are the largest class of plant secondary metabolites and are commonly found in essential oils. Monoterpenes and their derivatives are key ingredients in the design and production of new biologically active compounds. This review focuses on selected aliphatic, monocyclic, and bicyclic monoterpenes like geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures. The compounds in question play a pivotal role in biological and medical applications. The review also discusses anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, anticancer, antituberculosis, and antioxidant biological activities exhibited by monoterpenes and their derivatives. Particular attention is paid to the link between biological activity and the effect of structural modification of monoterpenes and monoterpenoids, as well as the introduction of various functionalized moieties into the molecules in question.

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“…In particular, several carvacrol ethers have been explored in the treatment of H. pylori bacterial infection and as antiproliferative agents against human gastric adenocarcinoma cell lines, with promising results [ 107 ]. Similarly, a metronidazole carvacrol ether derivative has shown remarkable activity against two strains of H. pylori and one strain of Clostridium perfringens ( Scheme 6 ) [ 108 ].…”

Section: Monophenolsmentioning

confidence: 99%

Tailored Functionalization of Natural Phenols to Improve Biological Activity

et al. 2021

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Phenols are widespread in nature, being the major components of several plants and essential oils. Natural phenols’ anti-microbial, anti-bacterial, anti-oxidant, pharmacological and nutritional properties are, nowadays, well established. Hence, given their peculiar biological role, numerous studies are currently ongoing to overcome their limitations, as well as to enhance their activity. In this review, the functionalization of selected natural phenols is critically examined, mainly highlighting their improved bioactivity after the proper chemical transformations. In particular, functionalization of the most abundant naturally occurring monophenols, diphenols, lipidic phenols, phenolic acids, polyphenols and curcumin derivatives is explored.

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Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol

Cited by 16 publications

References 34 publications

Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line

Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

Tailored Functionalization of Natural Phenols to Improve Biological Activity

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