Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics

Trukhanova, Yulia A.; Kolesnik, Denis A.; Kuvaeva, Elena V.; Ksenofontova, G. V.; Sopova, Marina V.; Yakovlev, I. P.

doi:10.3390/ecsoc-25-11773

Cited by 5 publications

(7 citation statements)

References 10 publications

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“…Previously, we have revealed high analgesic activity for a number of succinimide and phthalimide derivatives. [8,9] It was decided to conduct a comparative analysis of activity for new derivatives of glutarimide.…”

Section: Resultsmentioning

confidence: 99%

“…The analgesic activity of the test compound significantly exceeds the activity of the reference drug, and also exceeds the activity of pyrrolidine-2,5-dione derivatives. [8,9] The resulting glutarimide 4 a exhibits a similar level of analgesic activity at a concentration 5 times lower than that of pyrrolidine-2,5-dione deriva-tives. The results of the evaluation of analgesic activity are presented in Table 3.…”

Section: Resultsmentioning

confidence: 99%

“…In the literature, you can find a fairly large number of publications on methods for obtaining N-substituted glutarimide derivatives. [7] Previously, we investigated the reactions of obtaining Nsubstituted derivatives of pyrroliidine-2,5-dione [8] and isoindoline-1,3-dione, [9] carried out by the interaction of amber and phthalic anhydride with primary amines, namely, N-arylbenzamidines 1. At the same time, it was found that when succinimides are obtained, the reaction easily proceeds at ambient temperature in chloroform or dichloromethane, while the production of phthalimides requires boiling in an o-xylene medium with azeotropic distillation of water.…”

Section: Introductionmentioning

confidence: 99%

“…We have shown that the obtained succinimides and phthalimides have analgesic activity in the in vivo test. [8,9] It became interesting for us to investigate the conditions of the reaction for the production of piperidine-2,6-dione derivatives similarly to the reaction of glutaric anhydride and C,Ndiarylformamidines, as well as to study the biological activity of the derivatives obtained. It is worth noting that there is a very significant difference between 6-membered glutarimides and 5membered succinimides due to the steric properties of the ring on the conjugated amide and related bonds.…”

Section: Introductionmentioning

confidence: 99%

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Facile Directed Synthesis of (Z)‐1‐(Aryl(arylimino)methyl)piperidine‐2,6‐diones from C,N‐Diarylformamidines

et al. 2023

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A simple methodology has been developed for the synthesis of previously unstudied N‐substituted glutarimide derivatives ‐ (Z)‐1‐(aryl(arylimino)methyl)piperidine‐2,6‐diones 4 a–p obtained in one step from C,N‐diarylformamidines 1 a–p and glutaric anhydride 6 with product yields from 46 up to 88 % and chromatographic purity from 94 to 99 %. The structures of the obtained compounds were proved using NMR spectroscopy 1H, 13C, X‐ray diffraction analysis, mass spectroscopy, and elemental analysis. An in vivo study of the analgesic activity of a representative of series 4 a was carried out.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Facile Directed Synthesis of (Z)‐1‐(Aryl(arylimino)methyl)piperidine‐2,6‐diones from C,N‐Diarylformamidines

et al. 2023

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“…As shown in the synthetic route, oligoaniline was monofunctionalized via nucleophilic substitution (Scheme 1B)-under THF coupling conditions at the ambient temperature. 46,47 Biobased starshaped core (with four arms) was synthesized by the condensation reaction of PEN and L-LA (in stoichiometric scale) via a green approach-microwave irradiation with no solvents. Finally, S-PL endfunctionalized in a facile way via a microwave irradiation-induced esterification reaction.…”

Section: Total Acid Numbermentioning

confidence: 99%

Synthesis of multitask star‐shaped oligoaniline: Introducing a novel, efficient epoxy hardener

Shahkarami

Moini

Kabiri

et al. 2023

Polymers for Advanced Techs

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Multitask star-shaped oligoaniline (S-TAH) was synthesized using microwave irradiation in three steps: preparation of phthalic acid-capped tetra-aniline (as the arm), synthesis of a tetrafunctional biobased core, and subsequently, coupling arms to the core, using a divergent approach. A biobased core was synthesized through a direct condensation reaction of pentaerythritol, with L-lactic acid. The chemical structures were extensively characterized using Fourier-transform infrared and proton nuclear magnetic resonance spectroscopy. The performance of S-TAH, as a multitask hardener for bisphenol A-based epoxy resin (EP), was evaluated using differential scanning calorimetry, thermal gravimetric analysis, dynamic thermomechanical analyses (DMTA), and four-prob conductometry. Peaks of cure exotherms for S-TAH/EP (1:1) systems appear at 135 C with a tail-like peak around 175 C. Compared to conventional amine-cured EP, the thermal stability of the S-TAH/EP cured was significantly higher, that is, $ 40 C enhancement in half weight loss temperature (T 50 ). A threefold improvement in char yield was observed. From DMTA, the material cured with S-TAH displays representative storage moduli in glassy (9.4 GPa) and rubbery (5.2 GPa) states reflecting a uniform network and viscoelastic behavior. The electrical conductivities (σ) of the pure S-TAH and the epoxy systems cured with S-TAH/EP are 4.3 Â 10 À4 , and 2.65 Â 10 À4 , respectively. T star-shaped oligoaniline is a promising multitask hardener-functioning as hardener, thermal stabilizer, electrically conductive and toughening agents-which can be versatilely applied in thermal resistance anticorrosive coatings and conductive adhesives.

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C,N‐Diarylformamidines as Valuable Building Blocks in the Synthesis of Heterocyclic Compounds

et al. 2023

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Obtaining highly functionalized heterocyclic structures is an important topic of modern organic synthesis, as it reveals the possibility of constructing more complex systems and, thereby, expanding the range of various drugs. At the same time, in an effort to obtain a complex molecule from simple and available reagents, an interesting direction is the modification of C,N‐diarylformamidines , well known in medicinal chemistry. This literature review is comprehensive in the field of C,N‐diarylformamidine chemistry and covers publications on this topic from 1999 to 2022.

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Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics

Cited by 5 publications

References 10 publications

Facile Directed Synthesis of (Z)‐1‐(Aryl(arylimino)methyl)piperidine‐2,6‐diones from C,N‐Diarylformamidines

Facile Directed Synthesis of (Z)‐1‐(Aryl(arylimino)methyl)piperidine‐2,6‐diones from C,N‐Diarylformamidines

Synthesis of multitask star‐shaped oligoaniline: Introducing a novel, efficient epoxy hardener

C,N‐Diarylformamidines as Valuable Building Blocks in the Synthesis of Heterocyclic Compounds

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