Synthesis and antiviral activity of bis-spirocyclic derivatives of rhodanine

Kurbatov, S. V.; Zarubaev, Vladimir V.; Karpinskaya, L. A.; Швец, А. А.; Kletsky, Mikhail E.; Буров, Олег Н.; Morozov, P. G.; Киселев, О. И.

doi:10.1007/s11172-014-0560-4

Cited by 19 publications

(12 citation statements)

References 29 publications

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“…Among these, compound 50 exhibited the most potent inhibitory activity against the influenza virus A/California/07/09(H1N1) -pdm2009 replication (EC 50 = 1.9 μ g/mL) with high toxicity (CTD 50 = 37 μ g/mL), whereas compound 49 showed the lowest toxicity (CTD 50 = 415 μ g/mL) with moderate inhibition (EC 50 = 26.0 μ g/mL). 80 …”

Section: Anti-influenza Virus Agentsmentioning

confidence: 99%

Therapeutic Potential of Spirooxindoles as Antiviral Agents

et al. 2016

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Antiviral therapeutics with profiles of high potency, low resistance, panserotype, and low toxicity remain challenging, and obtaining such agents continues to be an active area of therapeutic development. Due to their unique three-dimensional structural features, spirooxindoles have been identified as privileged chemotypes for antiviral drug development. Among them, spiropyrazolopyridone oxindoles have been recently reported as potent inhibitors of dengue virus NS4B, leading to the discovery of an orally bioavailable preclinical candidate (R)-44 with excellent in vivo efficacy in a dengue viremia mouse model. This review highlights recent advances in the development of biologically active spirooxindoles for their antiviral potential, primarily focusing on the structure–activity relationships (SARs) and modes of action, as well as future directions to achieve more potent analogues toward a viable antiviral therapy.

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Section: Anti-influenza Virus Agentsmentioning

confidence: 99%

Therapeutic Potential of Spirooxindoles as Antiviral Agents

et al. 2016

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“…Over the last decade, a lot of publications have been devoted to the synthesis of dispiro compounds comprising pyrrolidine, oxindole, and other heterocycle moieties and to the evaluation of their physiological properties [24,26–32]. In this regard, our attention was directed towards hetero-annelated 1,2,4-triazines, because this motif is part of many natural and synthetic bioactive products [33–40].…”

Section: Introductionmentioning

confidence: 99%

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

Izmest’ev

Газиева

Sigay

et al. 2016

Beilstein J. Org. Chem.

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An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-6,3′-pyrrolidine-2′,3′′-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine moieties has been developed. The method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to 6-benzylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones.

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“…The goal of purposefully selecting rhodanine hybrids was to provide a wide range of pharmacological activities. Antibacterial [7], antifungal [8], antiviral [9], antimalarial [10], anti‐inflammatory [11], and anticancer properties have been linked to rhodanine‐based analogues [12,13]. The analogues of rhodanine with 2,4‐thiazolidinedione have a five‐membered heterocyclic core with >C═O group on the fourth carbon and have demonstrated a wide range of therapeutic effects [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation, and molecular docking study of thiophene‐, piperazine‐, and thiazolidinone‐based hybrids as potential antimicrobial agents

Desai

Rupala

Khasiya

et al. 2021

Journal of Heterocyclic Chem

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Antibiotic resistance in bacteria exacerbates the issue of antimicrobial resistance. Bacteria that cause common or serious infections have evolved resistance to every new antibiotic that has been introduced into the market, to varying degrees, over several decades. Faced with this reality, one of society's most urgent needs is for new antimicrobial drugs with novel mechanisms of action. With this objective, we describe here the development of a novel set of compounds including piperazine‐ and thiophene‐based thiazolidinones (5a–i) and thiophene‐thiazolidinones (6a–i). Compounds (5a–i) and (6a–i) were developed, synthesized, and tested for their antimicrobial activity, and their structures were elucidated with the help of various analytical techniques. Compounds 5a and 5d showed excellent antibacterial efficacy against Pseudomonas aeruginosa, with MICs of 50 μg/ml, whereas compounds 6c and 6e showed similar potency against Staphylococcus aureus and Escherichia coli, respectively. The antifungal efficacy of compounds 5e and 6i against Candida albicans was outstanding (MIC = 50 μg/ml). The only compound that had excellent antifungal efficacy against Aspergillus niger was compound 5e (MIC = 50 μg/ml). The chemico‐in silico‐biology approach could provide valuable insights into the potential of this novel hybridized scaffold for the development of promising antimicrobial agents.

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Synthesis and antiviral activity of bis-spirocyclic derivatives of rhodanine

Cited by 19 publications

References 29 publications

Therapeutic Potential of Spirooxindoles as Antiviral Agents

Therapeutic Potential of Spirooxindoles as Antiviral Agents

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

Synthesis, biological evaluation, and molecular docking study of thiophene‐, piperazine‐, and thiazolidinone‐based hybrids as potential antimicrobial agents

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