Synthesis and biological evaluation of 5-benzylidenerhodanine-3-acetic acid derivatives as AChE and 15-LOX inhibitors

Shafii, Negah; Khoobi, Mehdi; Amini, Mohsen; Sakhteman, Amirhossein; Nadri, Hamid; Moradi, Alireza; Emami, Saeed; Moghadam, Ebrahim Saeedian; Foroumadi, Alireza; Shafiee, Abbas

doi:10.3109/14756366.2014.940935

Cited by 23 publications

(6 citation statements)

References 23 publications

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“…Subsequently, materials such as N-3 and/or "active methylene" C-5 substitution can be found that are capable of generating potential new bioactive compounds and thus the new window has opened to medical science. As mentioned in previous sections, rhodanine has interesting properties which they can inhibit diverse enzymes, for instance deoxyxylulose 5-phosphate reductoisomerase [113], cholinesterases [114,115], 15-lipoxygenase [114], aldose reductase [116], dolicholphosphate mannose synthase [117], gyrase B [118], Mur ligases [119] and also augmentation of pathogenic protozoa [117], fungi [120], bacteria [31,113,121,122] and Mycobacterium tuberculosis [123] in whole-cell covering tests. It has been proven in the laboratory that rhodanines including those with C-5 substitution have the special ability to inhibit microbial enzymes and extensive anti-microbial activity.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

A conceptual review of rhodanine: current applications of antiviral drugs, anticancer and antimicrobial activities

Mousavi

Zarei

Hashemi

et al. 2019

Artificial Cells, Nanomedicine, and Biotechnology

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Rhodanines are accepted as advantaged heterocycles in medicinal chemistry as one of the 4-thiazolidinones subtypes. The aim of this paper is to analyze the features of rhodanine and its application in pharmacy and medicine. Some of the properties of rhodanine such as antiviral, anticancer, antimicrobial, and drug discovery have recently been reported. Although there are still vague points in the structure and mechanism of polymerization of this substance, there is a significant increase in the use of rhodanine in medicine. In this review paper, it can be said that we have provided a general overview of the recent advances in the rhodanine-based material which its application is more in the field of drug discovery and anticancer activity. The review starts with a summary of the antiviral activity of rhodanine-based materials and nanocomposites in general. Then in the next step, the detailed description is followed on their applications in the fields of anticancer activity, drug discovery, and an innovative type of rhodanine (RH) and thiohydantoin (TH) derivatives were created and combined in order to recognize tau pathology in the brains of patients with Alzheimer's disease (AD). Through this review, we hope to promote rhodanine and its role in medicine and pharmacy becomes more prominent.

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Section: Antimicrobial Activitymentioning

confidence: 99%

A conceptual review of rhodanine: current applications of antiviral drugs, anticancer and antimicrobial activities

Mousavi

Zarei

Hashemi

et al. 2019

Artificial Cells, Nanomedicine, and Biotechnology

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“…Furthermore, 5-arylidene derivatives of rhodanines were found to possess various types of activity, in particular antitumor [ 19 ], antiviral [ 20 , 21 ], anti-inflammatory, antidiabetic [ 22 , 23 , 24 ], antioxidant [ 25 ], LOX and cholinesterase inhibitory activities [ 26 , 27 ], as well as aldose reductase inhibitor activity [ 28 ]. There are many references in the literature regarding antimicrobial activity of rhodanine derivatives [ 14 , 29 , 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking Studies of 5-Indolylmethylen-4-oxo-2-thioxothiazolidine Derivatives

et al. 2022

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Background: Infectious diseases represent a significant global strain on public health security and impact on socio-economic stability all over the world. The increasing resistance to the current antimicrobial treatment has resulted in the crucial need for the discovery and development of novel entities for the infectious treatment with different modes of action that could target both sensitive and resistant strains. Methods: Compounds were synthesized using the classical organic chemistry methods. Prediction of biological activity spectra was carried out using PASS and PASS-based web applications. Pharmacophore modeling in LigandScout software was used for quantitative modeling of the antibacterial activity. Antimicrobial activity was evaluated using the microdilution method. AutoDock 4.2® software was used to elucidate probable bacterial and fungal molecular targets of the studied compounds. Results: All compounds exhibited better antibacterial potency than ampicillin against all bacteria tested. Three compounds were tested against resistant strains MRSA, P.aeruginosa and E.coli and were found to be more potent than MRSA than reference drugs. All compounds demonstrated a higher degree of antifungal activity than the reference drugs bifonazole (6–17-fold) and ketoconazole (13–52-fold). Three of the most active compounds could be considered for further development of the new, more potent antimicrobial agents. Conclusion: Compounds 5b (Z)-3-(3-hydroxyphenyl)-5-((1-methyl-1H-indol-3-yl)methylene)-2-thioxothiazolidin-4-one and 5g (Z)-3-[5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-yl]-benzoic acid as well as 5h (Z)-3-(5-((5-methoxy-1H-indol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)benzoic acid can be considered as lead compounds for further development of more potent and safe antibacterial and antifungal agents.

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“…Rhodanines′ (2-thioxothiazolidin-4-ones) privileged structure has attracted much attention in pharmaceutical and medicinal chemistry [ 1 , 2 ]. These substituted rhodanines have been discovered and reported for several pharmaceutical applications, including topoisomerase II inhibition potency [ 3 ]; potential AChE inhibitors [ 4 , 5 ]; HIV-1 integrase inhibitors [ 6 ]; anti-cancer agent towards MCF-7 breast cancer cells [ 7 ] and anti-diabetic (T2DM) targeting the inhibition of enzymes such as aldose reductase (ALR) [ 8 ], α-glucosidase [ 9 ], α-amylase [ 10 ] and PTP1B enzyme [ 11 ], and other therapeutic targets have also been reported, such as antibacterial ones [ 12 ]. Chemical modification, structural elucidation and molecular interactions investigations of these compounds are still of high interest.…”

Section: Introductionmentioning

confidence: 99%

Straightforward Regio- and Diastereoselective Synthesis, Molecular Structure, Intermolecular Interactions and Mechanistic Study of Spirooxindole-Engrafted Rhodanine Analogs

et al. 2021

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Straightforward regio- and diastereoselective synthesis of bi-spirooxindole-engrafted rhodanine analogs 5a–d were achieved by one-pot multicomponent [3 + 2] cycloaddition (32CA) reaction of stabilized azomethine ylide (AYs 3a–d) generated in situ by condensation of L-thioproline and 6-chloro-isatin with (E)-2-(5-(4-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)-N-(2-morpholinoethyl)acetamide. The bi-spirooxindole-engrafted rhodanine analogs were constructed with excellent diastereo- and regioselectivity along with high chemical yield. X-ray crystallographic investigations for hybrid 5a revealed the presence of four contiguous stereocenters related to C11, C12, C19 and C22 of the spiro structure. Hirshfeld calculations indicated the presence of many short intermolecular contacts such as Cl...C, S...S, S...H, O...H, N...H, H...C, C...C and H...H interactions. These contacts played a very important role in the crystal stability. The polar nature of the 32CA reaction was studied by analysis of the conceptual DFT reactivity indices. Theoretical study of this 32CA reaction indicated that it takes place through a non-concerted two-stage one-step mechanism associated with the nucleophilic attack of AY 3a to the electrophilic ethylene derivative.

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Synthesis and biological evaluation of 5-benzylidenerhodanine-3-acetic acid derivatives as AChE and 15-LOX inhibitors

Cited by 23 publications

References 23 publications

A conceptual review of rhodanine: current applications of antiviral drugs, anticancer and antimicrobial activities

A conceptual review of rhodanine: current applications of antiviral drugs, anticancer and antimicrobial activities

Synthesis, Biological Evaluation and Molecular Docking Studies of 5-Indolylmethylen-4-oxo-2-thioxothiazolidine Derivatives

Straightforward Regio- and Diastereoselective Synthesis, Molecular Structure, Intermolecular Interactions and Mechanistic Study of Spirooxindole-Engrafted Rhodanine Analogs

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