Synthesis of New N-Mono- and N,N-Dialkylated Imidazole Derivatives and Their Antiplatelet and Anticoagulation Activity

Гуревич, К. Г.; Ураков, А. Л.; Basantsev, A. V.; Самородов, Александр В.; Danilin, A. A.; Пурыгин, П. П.; Klenova, N. A.; Bashirov, I. I.; Баширова, Л. И.; Голованов, А. А.; Igorevich, Korunas Vladislav; Lipatov, D. O.

doi:10.1007/s11094-021-02395-z

Cited by 4 publications

(5 citation statements)

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“…The ionizing and aromatic imidazole ring promotes the pharmacokinetic characteristics of pharmaceuticals. Many newly synthesized imidazole derivatives have demonstrated high levels of anti-inflammatory, analgesic, antimicrobial, antiviral, antifungal, antituberculosis, antitumor, anticonvulsant, anticoagulant, and other types of activity in recent years, typically surpassing those of wellestablished medications with the appropriate mechanism of action (Kaldybayeva et al 2023;Fadhil and Qhanim 2020;Gas et al 2020;Rajam et al 2020;Wells et al 2020;Vidhya and Malar 2020;Gurevich et al 2021;Pham et al 2021;Patel et al 2022).…”

Section: Discussionmentioning

confidence: 99%

Study of the anti-inflammatory, analgesic, ulcerogenic and anti-ulcerogenic activity of N-isopropenylimidazole zinc complex derivative

Galenko-Yaroshevsky,

Shelemekh,

Popkov

et al. 2024

RRP

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Introduction: Although nonsteroidal anti-inflammatory drugs (NSAIDs) have a clear therapeutic benefit, they can also have serious side effects. The most serious of these is the ulcerogenic effect, which can result in a decline in the quality of life or even death. This calls for the search for and creation of novel compounds with potent anti-inflammatory properties that do not have adverse effects on the digestive system. The aim of the study was to investigate the anti-inflammatory, analgesic, ulcerogenic and anti-ulcerogenic activities of N-isopropenylimidazole zinc complex derivative. Materials and Methods: Experiments in rats and mice were used to determine the median lethal dose LD50 for N-isopropenylimidazole zinc complex derivative (laboratory name Pilim-1). Experimental models of acute exudative inflammation and chronic proliferative inflammation were used. In the first case, the inflammation was induced by sub-plantar injection of carrageenan and a complete Freund’s adjuvant into the hind paw of rats. In the second case, the inflammation was induced by the implantation of a sterile cotton pellet (“cotton pellet–induced granuloma”) under the skin of rats. Acute and tonic pain, visceral, and somatic deep pain were simulated using the formalin test in rats and the acetic acid-induced writhing test in mice, respectively. The ulcerogenic and anti-ulcerogenic effects of Pilim-1 were studied in rat experiments. Pilim-1 and the reference drugs diclofenac, indomethacin and famotidine were administered intragastrically. Results and Discussion: Pilim-1 showed marked anti-inflammatory and analgesic effects, demonstrated less toxicity than diclofenac and indomethacin, while its activity is comparable to diclofenac and superior to indomethacin. Its therapeutic index is higher than that of indomethacin and diclofenac and, in contrast, it essentially has no ulcerogenic effect and exhibits stronger anti-ulcerogenic activity than famotidine. It appears that the anti-inflammatory, analgesic, and gastroprotective properties of Pilim-1 are largely due to its antioxidant and antihypoxic properties, its inhibitory effects on cyclooxygenase and 5-lipoxygenase, and the presence of imidazole and zinc in its structure, both of which have a wide range of biological activity. Conclusion: Pilim-1 can be recommended for further preclinical studies due to its relatively low (practically absent) ulcerative activity, strong anti-inflammatory, analgesic, and anti-ulcerative effects, greater therapeutic index, and less acute toxicity in comparison with diclofenac and indomethacin.

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Section: Discussionmentioning

confidence: 99%

Study of the anti-inflammatory, analgesic, ulcerogenic and anti-ulcerogenic activity of N-isopropenylimidazole zinc complex derivative

Galenko-Yaroshevsky,

Shelemekh,

Popkov

et al. 2024

RRP

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“…The substituents of synthesized compounds and yields of all reactions are summarized in Table 2. The reaction between the 1-methyl-4-nitroimidazolole-2-carbohydrazide and appropriate isothiocyanate in boiling ethanol afforded thiosemicarbazides (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) in good yields of 81-85%. The structures of the new compounds, described for the first time, were determined using 1 H NMR spectroscopy and elemental analyses.…”

Section: Chemistrymentioning

confidence: 99%

“…The 1 H NMR spectra showed chemical shifts of protons located on nitrogen atoms as three singlets: one in the range of 9.46-10.04 ppm, the second in the range of 9.72-10.20 ppm, and the third in the range of 10.82-10.99 ppm. Signals of three protons of the methyl group in position N1 imidazole ring at 3.98-4.01 The reaction between the 1-methyl-4-nitroimidazolole-2-carbohydrazide and appropriate isothiocyanate in boiling ethanol afforded thiosemicarbazides (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) in good yields of 81-85%. The structures of the new compounds, described for the first time, were determined using 1 H NMR spectroscopy and elemental analyses.…”

Section: Chemistrymentioning

confidence: 99%

“…This made it possible to trace the relationship between the antimicrobial activity and structural differences in this group of compounds. A series of imidazole derivatives containing a thiosemicarbazide moiety (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) in their structure showed varied activity against Gram-positive bacteria with MIC values in the range of 31.25-1000 µg/mL, especially against S. epidermidis ATCC 12228, M. luteus ATCC 10240, B. subtilis ATCC 6633, and B. cereus ATCC 10876 (Table 2). Their activity was mostly bactericidal with MBC/MIC = 1-2.…”

Section: Antibacterial and Antifungal Activity Assaymentioning

confidence: 99%

“…This structure was discovered in the 1840s, arousing great interest among scientists involved in the design of new drugs [10]. This was due to the fact that compounds based on the imidazole core scaffold showed promising multidirectional effects, including anticancer [11,12], antimicrobial [6], antimycobacterial [13], analgesic [14], antidiabetic [15], antithrombotic [16], antiviral [17], antimalarial [18], anticonvulsant [19], and anti-inflammatory effects [20]. There are many drugs registered and used in clinical practice based on the imidazole core scaffold (Table 1).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Biological Evaluation of New Compounds with Nitroimidazole Moiety

Dziduch,

Janowska,

Andrzejczuk

et al. 2024

Molecules

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Heterocyclic compounds, particularly those containing azole rings, have shown extensive biological activity, including anticancer, antibacterial, and antifungal properties. Among these, the imidazole ring stands out due to its diverse therapeutic potential. In the presented study, we designed and synthesized a series of imidazole derivatives to identify compounds with high biological potential. We focused on two groups: thiosemicarbazide derivatives and hydrazone derivatives. We synthesized these compounds using conventional methods and confirmed their structures via nuclear magnetic resonance spectroscopy (NMR), MS, and elemental analysis, and then assessed their antibacterial and antifungal activities in vitro using the broth microdilution method against Gram-positive and Gram-negative bacteria, as well as Candida spp. strains. Our results showed that thiosemicarbazide derivatives exhibited varied activity against Gram-positive bacteria, with MIC values ranging from 31.25 to 1000 µg/mL. The hydrazone derivatives, however, did not display significant antibacterial activity. These findings suggest that structural modifications can significantly influence the antimicrobial efficacy of imidazole derivatives, highlighting the potential of thiosemicarbazide derivatives as promising candidates for further development in antibacterial therapies. Additionally, the cytotoxic activity against four cancer cell lines was evaluated. Two derivatives of hydrazide-hydrazone showed moderate anticancer activity.

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Synthesis, characterization and antifungal activity of imidazole chitosan derivatives

Wu,

Fan,

Shi

et al. 2024

Carbohydrate Research

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Synthesis of New N-Mono- and N,N-Dialkylated Imidazole Derivatives and Their Antiplatelet and Anticoagulation Activity

Cited by 4 publications

References 5 publications

Study of the anti-inflammatory, analgesic, ulcerogenic and anti-ulcerogenic activity of N-isopropenylimidazole zinc complex derivative

Study of the anti-inflammatory, analgesic, ulcerogenic and anti-ulcerogenic activity of N-isopropenylimidazole zinc complex derivative

Synthesis and Biological Evaluation of New Compounds with Nitroimidazole Moiety

Synthesis, characterization and antifungal activity of imidazole chitosan derivatives

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