Synthesis of novel 5-arylidenethiazolidinones with apoptotic properties via a three component reaction using piperidine as a bifunctional reagent

Bathula, Chandramohan; Tripathi, Sayantan; Srinivasan, Ramprasad; Jha, Kunal Kumar; Ganguli, Arnab; Chakrabarti, Gopal; Singh, Shailja; Munshi, Parthapratim; Sen, Subhabrata

doi:10.1039/c6ob01257d

Cited by 23 publications

(19 citation statements)

References 26 publications

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“…Although weak, the force provided by the polymeric surface is sufficient to immobilize the bait molecule. Based on this technology, a UPT-based protein target identification method was proposed 122 . After incubation with biological lysates, the protein targets were enriched in the prepared bait molecule-specific affinity matrix.…”

Section: Other New Label-free Screening Strategies-unique Polymer Tec...mentioning

confidence: 99%

An update of label-free protein target identification methods for natural active products

Cui¹,

Li²,

Chen³

et al. 2022

Theranostics

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Natural active products (NAPs) are derived from chemical substances found in nature that have biological activity and medicinal potential. Screening and revealing the protein targets of NAPs is an indispensable link in the pharmacological and toxicological understanding of NAPs. Proteins are the main factors executing cell functions, and cells rely on the function of proteins to complete various activities in the life cycle. The important mechanism of action of drugs is to regulate cell biological activities by interacting with proteins and other macromolecules. At present, the classic way to screen protein targets is based on the molecular label tracing method, which has a long cycle and changes the molecular structure and pharmacological effects of NAPs. Due to the shortcomings of molecular labelling methods, in recent years, scientists have tried to develop a variety of label-free protein target identification methods for NAPs and have made a certain amount of progress. This article reviews the current protein target identification methods for NAPs with the aim of providing a reference for research on NAP protein targets.

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Section: Other New Label-free Screening Strategies-unique Polymer Tec...mentioning

confidence: 99%

An update of label-free protein target identification methods for natural active products

Cui¹,

Li²,

Chen³

et al. 2022

Theranostics

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“…The indole ring was found not only in natural compounds but also in diverse semisynthetic and synthetic drug-like molecules [ 32 , 33 ]. They exhibit antimicrobial [ 34 , 35 , 36 , 37 , 38 , 39 ], anti-inflammatory [ 40 , 41 ], COX inhibitory [ 42 , 43 ] anticancer [ 44 , 45 , 46 ], antiviral [ 47 , 48 ], anti-HIV [ 49 , 50 ], and antidiabetic [ 51 ] activities. Among the natural compounds containing the indolene fragment, several imidazoline and imidazolidine alkaloids are known, which have a wide spectrum of biological activity, including antibacterial.…”

Section: Introductionmentioning

confidence: 99%

“…They exhibit antimicrobial [34][35][36][37][38][39], anti-inflammatory [40,41], COX inhibitory [42,43] anticancer [44][45][46], antiviral [47,48], anti-HIV [49,50], and antidiabetic [51] activities. Among the natural compounds containing the indolene fragment, several imidazoline and imidazolidine alkaloids are known, which have a wide spectrum of biological activity, including antibacterial.…”

Section: Introductionmentioning

confidence: 99%

3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation

Horishny

Карцев²,

Matiychuk

et al. 2020

Pharmaceuticals

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Herein we report the design, synthesis, computational, and experimental evaluation of the antimicrobial activity of fourteen new 3-amino-5-(indol-3-yl) methylene-4-oxo-2-thioxothiazolidine derivatives. The structures were designed, and their antimicrobial activity and toxicity were predicted in silico. All synthesized compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin and (for the majority of compounds) streptomycin. The most sensitive bacterium was S. aureus (American Type Culture Collection ATCC 6538), while L. monocytogenes (NCTC 7973) was the most resistant. The best antibacterial activity was observed for compound 5d (Z)-N-(5-((1H-indol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-4-hydroxybenzamide (Minimal inhibitory concentration, MIC at 37.9–113.8 μM, and Minimal bactericidal concentration MBC at 57.8–118.3 μM). Three most active compounds 5d, 5g, and 5k being evaluated against three resistant strains, Methicillin resistant Staphilococcus aureus (MRSA), P. aeruginosa, and E. coli, were more potent against MRSA than ampicillin (MIC at 248–372 μM, MBC at 372–1240 μM). At the same time, streptomycin (MIC at 43–172 μM, MBC at 86–344 μM) did not show bactericidal activity at all. The compound 5d was also more active than ampicillin towards resistant P. aeruginosa strain. Antifungal activity of all compounds exceeded those of the reference antifungal agents bifonazole (MIC at 480–640 μM, and MFC at 640–800 μM) and ketoconazole (MIC 285–475 μM and MFC 380–950 μM). The best activity was exhibited by compound 5g. The most sensitive fungal was T. viride (IAM 5061), while A. fumigatus (human isolate) was the most resistant. Low cytotoxicity against HEK-293 human embryonic kidney cell line and reasonable selectivity indices were shown for the most active compounds 5d, 5g, 5k, 7c using thiazolyl blue tetrazolium bromide MTT assay. The docking studies indicated a probable involvement of E. coli Mur B inhibition in the antibacterial action, while CYP51 inhibition is likely responsible for the antifungal activity of the tested compounds.

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“…4-Thiazolidinones are a promising class of heterocyclic scaffolds in the field of pharmaceutical chemistry [1–4]. In particular, 2-amino-5-arylidene-1,3-thiazol-4(5 H )-one derivatives exhibited potential and interesting broad medicinal activities, for example, antiviral, antibacterial, anti-inflammatory and cardiotonic [5–9]. In order to prepare such heterocyclic moiety, several synthetic strategies have been established [10–12], but these reported protocols necessitate multi-steps, elevated temperature, laborious work-up and long reaction times.…”

Section: Introductionmentioning

confidence: 99%

New dicationic DABCO-based ionic liquids: a scalable metal-free one-pot synthesis of bis-2-amino-5-arylidenethiazol-4-ones

Arafa

Mourad

2019

R. Soc. open sci.

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Herein, a novel DABCO-based dicationic ionic liquid (bis-DIL) was easily prepared from the sonication of DABCO with 1,3-dichloro-2-propanol and then characterized by several techniques. Thereafter, under the ultimate green conditions, the performance of the bis-DIL was examined for the sono-synthesis of a new library of bis-2-amino-5-arylidenethiazol-4-ones via one-pot pseudo-five-component Knoevenagel condensation reaction of appropriate dialdehydes, rhodanine and amines. This protocol is tolerant towards several mono- and dialdehydes, excellently high yielding and affording access to the desired products in a single step within a short reaction time. Compared with the conventional methodologies, the proposed method displayed several remarkable merits such as milder reaction conditions without any side product, green solvent media, recording well in a variety of green metrics and applicability in gram-scale production. The recyclability of the bis-DIL was also investigated with an average recovered yield of 97% for six sequential cycles without any significant loss of the activity.

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Synthesis of novel 5-arylidenethiazolidinones with apoptotic properties via a three component reaction using piperidine as a bifunctional reagent

Cited by 23 publications

References 26 publications

An update of label-free protein target identification methods for natural active products

An update of label-free protein target identification methods for natural active products

3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation

New dicationic DABCO-based ionic liquids: a scalable metal-free one-pot synthesis of bis-2-amino-5-arylidenethiazol-4-ones

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