Design, synthesis, and anticonvulsant evaluation of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives

Mokrov, G. V.; Литвинова, С. А.; Воронина, Т. А.; Nerobkova, L. N.; Kutepova, I. S.; Kovalev, I. G.; Gudasheva, T. A.; Дурнев, А. Д.

doi:10.1007/s00044-019-02422-5

Cited by 7 publications

(6 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the test with scPTZ, compound ( 41c ) (at doses of 10–40 mg/kg) was the most active; it contains GABA pharmacophore in the form of methyl ester and coumarin with two ‐nitro groups. SAR study reveals compounds with a coumarin heterocyclic core and with unsubstituted GABA pharmacophore were more active in the MES test, and compounds with GABA methyl ester exhibited more activity in the test with scPTZ 88,89 …”

Section: Resultsmentioning

confidence: 99%

“…SAR study reveals compounds with a coumarin heterocyclic core and with unsubstituted GABA pharmacophore were more active in the MES test, and compounds with GABA methyl ester exhibited more activity in the test with scPTZ. 88,89 Walaa and co-workers synthesized different coumarin hybrids and screened for their anticonvulsant profile using through MES, scPTZ and rotarod methods. Compounds ( 42), ( 43) and (44a) disclosed the highest potency among the series with 100% protection against scPTZ.…”

Section: Ronad and Co-workers Developed Series Coumarin-schiff Basementioning

confidence: 99%

See 1 more Smart Citation

Synthetic and natural coumarins as potent anticonvulsant agents: A review with structure–activity relationship

Keri

Budagumpi

Somappa

2022

Clinical Pharmacy Therapeu

View full text Add to dashboard Cite

What is known and objective:The main objective of this review is to highlight the most relevant studies since 1990 (to date) in the area of medicinal chemistry aspects to provide a panoramic view to the biologists/medicinal chemists working in this area and would assist them in their efforts to design, synthesize and extract (from natural source) coumarin-based anticonvulsant agents. Also, the structure-activity relationship (SAR) studies are also discussed for further rational design of this kind of derivatives. It is hoped that this review will be helpful for new thoughts in the quest for rational designs of more active and less toxic coumarin-based antiepileptic agents.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Ronad and Co-workers Developed Series Coumarin-schiff Basementioning

confidence: 99%

Synthetic and natural coumarins as potent anticonvulsant agents: A review with structure–activity relationship

Keri

Budagumpi

Somappa

2022

Clinical Pharmacy Therapeu

View full text Add to dashboard Cite

show abstract

“…The strategy implemented for the synthesis of 4-hydroxy-3-(substituted-1-ylmethyl) quinolin-2(1H)-one derivatives is described in Scheme 1 . The starting material constituting of dianilides N1, N3- diphenyl/bis(4-chlorophenyl)/bis (4- fluorophenyl)/di-(p-tolyl) malonamide (1a/1b/1c/1d) were synthesized as described in the literature ( Mokrov et al, 2019 ). Table 1 illustrates the structures of the intermediates and synthesized compounds along with their IUPAC names.…”

Section: Resultsmentioning

confidence: 99%

Identification of Linomide Derivatives as Potential Anticancer Therapeutics using Molecular Docking Studies

Soares

Bhattacharya²,

Mamledesai³

et al. 2022

Front. Pharmacol.

View full text Add to dashboard Cite

12 analogs bearing a structural similarity to Linomide, a bonafide anticancer agent were synthesized wherein cyclization of substituted dianilides rendered 4-hydroxyquinolin-2(1H)-ones that were subjected to a Mannich reaction to yield 4-hydroxy-3-(substituted-1-ylmethyl) quinolin-2(1H)-one analogs. Characterization was performed using IR, 1H nuclear magnetic resonance and 13C NMR spectral analysis. Subsequently, in vitro anticancer studies revealed that Compound 4b showed maximum cytotoxicity with IC50 values of 1.539 μM/ml and 1.732 μM/ml against A549 and K562 cell lines respectively. This, however, is lower in comparison with standard Paclitaxel (IC50 values of 0.3 μM/ml for both cell lines). Surprisingly, docking studies at the active site of EGFRK revealed Compound 4b possessed a MolDock Score of -110.2253 that is highly comparable to the standard 4-anilinoquinazoline (MolDock Score of -112.04). Our computational and biological data thus provides an insight on the cytotoxicity of these derivatives and warrants future research that can possibly lead to the development of potent anticancer therapeutics.

show abstract

“…Few papers per year describe some new advances in the field, related to both synthesis and biological applications. In 2019, there are only four relevant references on this topic, with the first one being a chemical mechanistic approach on the formation of two-center three-electron bonds by the hydroxyl radical induced reaction of thioesculetin [ 17 , 18 , 19 , 20 ]. The second study is focused on the anticonvulsant activity of a new series of synthetic 4-amino-3-nitrothiocoumarins [ 18 ].…”

Section: Discussionmentioning

confidence: 99%

“…However, further reports for other substituted thiocoumarins were lower than these. In this recent manuscript [ 19 ], an alternative two-step method has been proposed by the authors ( Figure 2 ). An intermediate dithiophenyl ester of malonic acid is formed in high yield, using moderate conditions.…”

Section: Discussionmentioning

confidence: 99%

Thiocoumarins: From the Synthesis to the Biological Applications

et al. 2022

View full text Add to dashboard Cite

Coumarin is a privilege scaffold in medicinal chemistry. Coumarin derivatives are still an emerging class of highly potent pharmaceutical drugs, best known in the field of antimicrobials and anticoagulants. Thiocoumarins are a particular class of coumarins in which one or two of the oxygen atoms are replaced by a sulfur. They are chemically subdivided in three groups: Thiocoumarins, 2-thioxocoumarins, and dithiocoumarins. This review emphasizes the rationale behind the synthesis and biological applications of the most relevant publications related to this family of compounds. Particular attention has been given to their potential as drug candidates, with particular emphasis in the last 5 years. This article is based on the most relevant information collected from multiple electronic databases, including SciFinder, Pubmed, Espacenet, and Mendeley.

show abstract

Design, synthesis, and anticonvulsant evaluation of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives

Cited by 7 publications

References 23 publications

Synthetic and natural coumarins as potent anticonvulsant agents: A review with structure–activity relationship

Synthetic and natural coumarins as potent anticonvulsant agents: A review with structure–activity relationship

Identification of Linomide Derivatives as Potential Anticancer Therapeutics using Molecular Docking Studies

Thiocoumarins: From the Synthesis to the Biological Applications

Contact Info

Product

Resources

About