Synthesis of indoline-thiazolidinone hybrids with antibacterial and antifungal activities

Konechnyi, Yulian; Lozynskyi, Andrii; Horishny, V. Ya.; Konechna, Roksolana; Vynnytska, Renata; Korniychuk, Olena; Lesyk, Roman

doi:10.7124/bc.000a3a

Cited by 10 publications

(10 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All compounds have been assessed for their ADMET profile in ADMET Predictor version 10.4 provided by the Simulation Plus software package [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ...…”

Section: Resultsmentioning

confidence: 99%

“…So far, many indole-based rhodanine derivatives ( Figure 3 ) have been proposed [ 6 , 41 , 45 , 46 , 47 , 48 , 49 ] as antimicrobial agents, some of which possess high efficacy in treating multi-drug resistant pathogens [ 6 , 41 , 47 , 48 , 49 ]. Therefore, it is noteworthy that the combination of indole and rhodanine scaffolds into new chemical entities could be a promising strategy for antimicrobial therapies.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylates as Antimicrobial Agents—In Silico and In Vitro Evaluation

et al. 2023

View full text Add to dashboard Cite

Herein, we report the experimental evaluation of the antimicrobial activity of seventeen new (Z)-methyl 3-(4-oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylate derivatives. All tested compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin as well as streptomycin by 10–50 fold. The most sensitive bacterium was En. Cloacae, while E. coli was the most resistant one, followed by M. flavus. The most active compound appeared to be compound 8 with MIC at 0.004–0.03 mg/mL and MBC at 0.008–0.06 mg/mL. The antifungal activity of tested compounds was good to excellent with MIC in the range of 0.004–0.06 mg/mL, with compound 15 being the most potent. T. viride was the most sensitive fungal, while A. fumigatus was the most resistant one. Docking studies revealed that the inhibition of E. coli MurB is probably responsible for their antibacterial activity, while 14a–lanosterol demethylase of CYP51Ca is involved in the mechanism of antifungal activity. Furthermore, drug-likeness and ADMET profile prediction were performed. Finally, the cytotoxicity studies were performed for the most active compounds using MTT assay against normal MRC5 cells.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylates as Antimicrobial Agents—In Silico and In Vitro Evaluation

et al. 2023

View full text Add to dashboard Cite

show abstract

“…The reaction mixture is boiled for three hours and cooled. The reaction product is filtered off and recrystallized from acetic acid [8]. The structure and purity of the synthesized compound were confirmed by 1 H and 13 C NMR spectroscopy and mass spectrometry.…”

Section: Materials and Methods Of The Research Synthesis Of 3-[5-(1h-indol-3-ylmethylene)-4oxo-2-thioxo-thiazolidin-3-yl]-propionic Acidmentioning

confidence: 99%

“…4-thiazolidinone derivatives are an important class of "drug-like" molecules with anticancer [3,4], antiprypanosomal [5], antiviral [6], antimicrobial [7], antifungal [8], anti-inflammatory [9], antioxidant [10] activity. In addition, the thiazole heterocycle is present in drugs with antimicrobial activity, such as penicillin, monobactam, sulfathiazole, thiabendazole, nizatidine, as well as drugs for the treatment of cancer, such as sunitinib, which makes thiazole/thiazolidinone derivatives a potential source of new agents with polytargetative action.…”

Section: Introductionmentioning

confidence: 99%

Cell immunity of laboratory animals under the influence of 5-indolylmethylene rhodanine-3-carboxylic/sulphonic acid derivative

Konechnyi¹,

Hrushka²,

Pryzyhley³

et al. 2021

SR: PS

View full text Add to dashboard Cite

The aim. To study the cell immunity status under influence of 3-[5-(1H-indol-3-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-yl]-propionic acid, as a prominent 4-thiazolidinone derivative and a class of biologically active compounds with polypharmacological properties. Materials and methods. Experimental method on the model of laboratory animals (guinea pigs); intradermal allergy tests; relative and absolute content in the peripheral blood of T- and B-lymphocytes subpopulations; hematological indexies: index of the ratio of lymphocytes and monocytes, index of the ratio of neutrophils and monocytes, index of the ratio of neutrophils and eosinophils, phagocytic index, phagocytic number; ELISA; organic synthesis; pharmacological screening. Results. The effect of 3-[5-(1H-indol-3-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-yl]-propionic acid has antifungal properties and affect cellular component of immunity in vivo in the guinea pigs model. There are no changes in the skin of guinea pigs during and after chemical applications of the skin and after intradermal tests. The compound stimulate the immune cells, in particular the lymphocyte (increase in the absolute number of CD3 T-lymphocytes by 21.46 % and the absolute number of CD8 T-suppressors by 27.15 %), but with a selective inhibitory effect on certain units (decrease the relative number of NK cells CD16 by 11.57 % and B-lymphocytes CD22 by 23.08 %). There was an increase in the activity of the macrophage phagocytic system (increase in PN by 439.87 % and PI by 62.73 % at 120 minutes), which indicates the reliability of the absorbing function of phagocytes, but with a decrease in their ability to endocytosis (PCI decreased significantly by 78,72 %). Conclusions. Synthesized 3-[5-(1H-indol-3-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-yl]-propionic acid has a selective activating effect on certain parts of cellular immunity and on phagocytic activity. Derivate influence on the phagocytic activity of neutrophils is ambiguous, and the effect of the compound directed to the cellular part of the immune system does not cause cellular immunodeficiency. The studied derivative is promising for further study of the drug-like molecule with antifungal and antitumor effects

show abstract

“…The compound 118 with ethanesulfonic acid substituent of rhodanine scaffold at N-3 and indole-3-ylmethylene at C-5 showed the highest antibacterial activity. [32] Kryshchyshyn-Dylevych et al synthesized 4-thiazolidinoneindole hybrid derivatives 119-121 using a mild and efficient method (Figure 19). They were further screened against various cancer cell lines.…”

Section: Pharmacological Significance and Sarmentioning

confidence: 99%

Rhodanine‐Incorporated Indole Derivatives as Pharmacologically Vital Hybrids

2022

View full text Add to dashboard Cite

Nowadays, some life-threatening diseases keep individuals living in fear of death and experiencing health losses that were before unexpected. Therefore, there is an urgent need for the development of active pharmacological agents to minimize the injurious effect of such diseases. For that, numerous heterocyclic compounds and their hybrids have been designed, developed, and synthesized. They are also considered to be more effective against microorganisms that have developed multi-drug resistance. 2-Thioxo-4-thiazolidinone (rhodanine) and indole are regarded as advantageous heterocycles in medicinal chemistry. The pharmacological properties of rhodanine scaffolds can be improved by incorporating indole moieties. The present review expresses the pharmacological advances of rhodanine-incorporated indole derivatives along with their structure-activity relationships (SAR). To find novel drugs and combat serious diseases, we have observed that such hybrid structures are more effective pharmacophores than single motifs.

show abstract

Synthesis of indoline-thiazolidinone hybrids with antibacterial and antifungal activities

Cited by 10 publications

References 37 publications

N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylates as Antimicrobial Agents—In Silico and In Vitro Evaluation

N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylates as Antimicrobial Agents—In Silico and In Vitro Evaluation

Cell immunity of laboratory animals under the influence of 5-indolylmethylene rhodanine-3-carboxylic/sulphonic acid derivative

Rhodanine‐Incorporated Indole Derivatives as Pharmacologically Vital Hybrids

Contact Info

Product

Resources

About