Synthesis and antibacterial activity evaluation of novel rhodanine based amide derivatives

Tarahomi, Mehrasa; Baharfar, Robabeh; Mohseni, Mojtaba

doi:10.15761/cmid.1000157

Cited by 5 publications

(4 citation statements)

References 24 publications

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“…Compounds 42b , 42c , and 42h showed good inhibitory activity against gram‐positive bacteria (zone of inhibition = 8–14.5 mm) and remained inactive toward gram‐negative bacteria. Furthermore, compound 42d displayed good activity in all bacterial strains, excluding B. subtilis (Tarahomi et al, 2019).…”

Section: Biological Spectrum Of Rhodanine Derivativesmentioning

confidence: 99%

Rhodanine derivatives: An insight into the synthetic and medicinal perspectives as antimicrobial and antiviral agents

et al. 2022

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Rhodanine or 2-Thioxothiazolidin-4-one is a privileged heterocyclic compound offering a wide opportunity for structural modification, lead development, and modification. It is one of the highly decorated scaffolds in the drug discovery process. Rhodanine derivatives possess a plethora of biological activities due to their ability to interact with a diverse range of protein targets, which provide tremendous opportunities to discover new drugs with different modes of action. The most common strategy for developing novel rhodanine derivatives is the introduction of structurally diverse substituents at the C-5 or N-3, or both positions. Since the inception of Epralestat into the market in 1992, the exploration of rhodanine-3acetic acids has led to the development of novel leads against different biological targets such as MRSA, HHV-6, Mycobacterial tuberculosis, dengue, etc. In the current pandemic era, some rhodanine compounds have been explored against SARS-CoV-2. In recent years, rhodanine and its derivatives have witnessed significant progress in developing new drug leads as potential antimicrobial and antiviral agents. Different synthetic methodologies and recent developments in the medicinal chemistry of rhodanine derivatives, including biological activities, their mechanistic aspects, structure-activity relationships, and in silico findings, have been compiled in the present review. This article will benefit the scientific community and offer perspectives on how these scaffolds as privileged structures might be exploited in the future for rational design and discovery of rhodaninebased bio-active molecules.

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Section: Biological Spectrum Of Rhodanine Derivativesmentioning

confidence: 99%

Rhodanine derivatives: An insight into the synthetic and medicinal perspectives as antimicrobial and antiviral agents

et al. 2022

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“…A simple one-step condensation of rhodanine and an aldehyde provides access to a large number of derivatives, which usually do not require column chromatography for purification. The thus-obtained structures are well established motifs in different areas of research such as fluorophore design, ion sensing, solar-cell dyes, − and medicinal and biological chemistry. − For example, a number of widely used kinase inhibitors such as SMI-16a , or SMI-4a , with activity against PIM (Provirus Integration site for Moloney leukemia virus) kinases − are based on this structural motif. Despite this great versatility, only the related dicyanorhodanine structure in conjunction with thiophenes , and related solar cell dye structures , were shown to undergo photoisomerization so far.…”

Section: Introductionmentioning

confidence: 99%

Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis

Köttner,

Wolff,

Mayer

et al. 2024

J. Am. Chem. Soc.

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Molecular photoswitches are highly desirable in all chemistry-related areas of research. They provide effective outside control over geometric and electronic changes at the nanoscale using an easy to apply, waste-free stimulus. However, simple and effective access to such molecular tools is typically not granted, and elaborate syntheses and substitution schemes are needed in order to obtain efficient photoswitching properties. Here we present a series of rhodanine-based photoswitches that can be prepared in one simple synthetic step without requiring elaborate purification. Photoswitching is induced by UV and visible light in both switching directions, and thermal stabilities of the metastable states as well as quantum yields are very high. An additional benefit is the hydrogen-bonding capacity of the rhodanine fragment, which enables applications in supramolecular or medicinal chemistry. We further show that the known rhodanine-based inhibitor SMI-16a is a photoswitchable apoptosis inducer. The biological activity of SMI-16a can effectively be switched ON or OFF by reversible photoisomerization between the inactive E and the active Z isomer. Rhodanine-based photoswitches therefore represent an easy to access and highly valuable molecular toolbox for implementing light responsiveness to the breadth of functional molecular systems.

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“…Compounds containing the 2-sulfanylidene-1,3-thiazolidin-4-one core (rhodanine), the synthesis of which was first carried out by Nencki almost 150 years ago [1], have interesting biological properties and therefore are still of interest to researchers in the field of medicinal chemistry [2][3][4]. Such derivatives reveal, inter alia, antibacterial [5,6], antifungal [7,8], antiviral [9,10], antitumor [11][12][13][14], anti-inflammatory [15] and anthelmintic [16] activities. Other, non-medical applications of rhodanine derivatives are also known.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives

et al. 2022

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The constant increase in the resistance of pathogenic bacteria to the commonly used drugs so far makes it necessary to search for new substances with antibacterial activity. Taking up this challenge, we obtained a series of rhodanine-3-carboxyalkyl acid derivatives containing 2- or 3- or 4-pyridinyl moiety at the C-5 position. These compounds were tested for their antibacterial and antifungal activities. They showed activity against Gram-positive bacteria while they were inactive against Gram-negative bacteria and yeast. In order to explain the relationship between the activity of the compounds and their structure, for selected derivatives crystal structures were determined using the X-ray diffraction method. Modeling of the isosurface of electron density was also performed. For all tested compounds their lipophilicity was determined by the RP-TLC method and by calculation methods. On the basis of the carried-out research, it was found that the derivatives with 1.5 N···S electrostatics interactions between the nitrogen atom in the pyridine moiety and the sulfur atom in the rhodanine system showed the highest biological activity.

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Synthesis and antibacterial activity evaluation of novel rhodanine based amide derivatives

Cited by 5 publications

References 24 publications

Rhodanine derivatives: An insight into the synthetic and medicinal perspectives as antimicrobial and antiviral agents

Rhodanine derivatives: An insight into the synthetic and medicinal perspectives as antimicrobial and antiviral agents

Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis

Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives

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