Synthesis of Isoxazole and 1,2,3-Triazole Isoindole Derivatives via Silver- and Copper-Catalyzed 1,3-Dipolar Cycloaddition Reaction

Rammah, Mohamed M.; Gati, Wafa; Mtiraoui, Hasan; Ciamala, Kabula; Knorr, Michael; Rousselin, Yoann; Kubicki, Marek M.

doi:10.3390/molecules21030307

Cited by 13 publications

(12 citation statements)

References 53 publications

(66 reference statements)

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“…On the other hand, the 1 H NMR spectrum of 5a displays the resonance of the isoxazole proton as a singlet at δ = 6.49 ppm. This chemical shift is in line with the values reported by Fokin and Sharpless and our previous work . In the case of reverse regioisomers, isoxazole proton should resonate at a chemical shift higher than 6.5 ppm because of the proximity of the isoxazolinic oxygen atom particularly characteristic are the 13 C NMR isoxazole ring resonances with three peaks at δ = 101.2, 162.7, and 166.0 ppm, in accordance with the data reported by Fokin and Sharpless …”

Section: Resultssupporting

confidence: 92%

Synthesis of New Spirooxindole‐Fused Isoxazoline/Triazole and Isoxazoline/Isoxazole Derivatives from Three‐Component 1,3‐Dipolar Cycloaddition

Sakly

Edziri

Askri

et al. 2017

Journal of Heterocyclic Chem

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A series of diverse heterocycles containing spirooxindole, isoxazoline/triazole, and isoxazole rings has been synthesized via an efficient three‐component reaction of (E)‐2‐(1‐propargyl‐2‐oxoindoline‐3‐ylidene)acetophenones 1, arylnitrile oxides 2, and arylazides 3 using Cu(I) as catalyst. The regiochemistry and stereochemistry of cycloadducts 4a and 5a have been confirmed by X‐ray diffraction studies. The heterocycles were screened against Gram‐positive and Gram‐negative bacteria and fungi. Several compounds exhibit moderate to excellent activities comparable to those of established standard drugs.

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Section: Resultssupporting

confidence: 92%

Synthesis of New Spirooxindole‐Fused Isoxazoline/Triazole and Isoxazoline/Isoxazole Derivatives from Three‐Component 1,3‐Dipolar Cycloaddition

Sakly

Edziri

Askri

et al. 2017

Journal of Heterocyclic Chem

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“…Both these moieties have physicochemical and pharmacokinetic similarities and individually have been integrated at the place of ethylene bridge for cis configuration rigidification of CA‐4 (compound 6 & 8 , Figure ). Earlier reported synthetic derivatives of CA‐4 also had retained the original anti‐tubulin target specificity . The isoxazoline and 1, 2, 3‐ triazole are enriched with lone pair of electrons along with pi electrons in the double bonds which impart non‐covalent interactions.…”

Section: Introductionmentioning

confidence: 97%

“…Earlier reported synthetic derivatives of CA-4 also had retained the original anti-tubulin target specificity. [22][23][24][25][26][27][28][29][30][31][32][33][34][35] The isoxazoline and 1, 2, 3-triazole are enriched with lone pair of electrons along with pi electrons in the double bonds which impart noncovalent interactions. Both moieties show biological potential with a plethora of pharmacological effects on varying connecting molecular-skeletal combinations.…”

Section: Introductionmentioning

confidence: 99%

“…[23,28,29,[31][32][33][34]36,37] Although their incorporation increases the size of the molecule; it may maintain or enhance the cytotoxicity of the derived molecules and could also enhance binding interactions at CBS site. [22][23][24]30,32,34,[37][38][39][40][41][42][43][44] It is evident from the synthesized analogues reported earlier on CA-4 derivatives that the 'A ring' with the tri-methoxy group as the substituent is significant in maintaining potency ( Figure 2). However, replacement of trimethoxy group with chlorine, fluorine, incorporation of big size groups also has resulted in favourable retention of activity and potency.…”

Section: Introductionmentioning

confidence: 99%

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Design and Synthesis of New Tubulin Polymerization Inhibitors Inspired from Combretastatin A‐4: An Anticancer Agent

et al. 2020

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A series of 30 small hybrid molecules are synthesized inspired from Combretastatin A-4 (CA-4), where ethylene-bridge of CA-4 is replaced with two five-membered heterocyclic rings, viz. isoxazoline and 1, 2, 3-triazole. These are joined by a methylene linker, with substitutions at A and Bring position of CA-4. The new molecular entities have shown significant cytotoxicity to cancer cell from the IC 50 0.49 μM-3.17 μM with 1-((4,5-Dihydro-3-(2,5-dimethoxyphenyl)isoxazol-5-yl)methyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole displayed IC 50 0.422 � 0.07 μM for A-549-lung cancer cell line and IC 50 0.498 � 0.03 μM for MDA-MB-231-breast cancer cell line. The western blot analysis, confocal staining and also by in vitro tubulin polymerization assay established the target specificity of the molecules as a tubulin polymerization inhibitor. Molecular docking & Molecular dynamics studies confirmed the binding interaction patterns of these molecules at the Colchicine binding site of tubulin and have correlated the observed experimental result with variation in structure satisfactorily.

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“…Silver and copper are reported as catalysts, in a new and efficient way, for the cycloaddition of propargyl-substituted dihydroisoindolin-1-one with arylnitrile oxides to produce novel 3,5-disubstituted isoxazoles of the ethyl-2-benzyl-3-oxo-1-((3-arylisoxazol-5yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylate type [2]. Yields are significantly improved with the presence of Cu I as catalyst compared to the uncatalyzed reaction, without changing the selectivity.…”

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confidence: 99%

Special Issue: Coinage Metal (Copper, Silver, and Gold) Catalysis

Carabineiro

2016

Molecules

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Abstract:The subject of catalysis by coinage metals (copper, silver, and gold) comes up increasingly day-by-day. This Special Issue aims to cover the numerous aspects of the use of these metals as catalysts for several reactions. It deals with synthesis and characterization of copper, silver and gold based catalysis, their characterization and use, both for heterogeneous and homogeneous catalysis, and some of their potential applications.Keywords: copper; silver; gold; catalysis; selectivity Catalysts are materials that allow important reactions to be more selective, faster and require less energy. Coinage metals (copper, silver, and gold) are often found as important components of most catalysts and are known for their high activity and important properties. Thus the demand for research on this topic is continuously increasing.This Special Issue aims to cover several aspects of the usage of Cu, Ag and Au as catalysts for both homogenous and heterogeneous catalysis. It consists of nine important "cutting-edge" open access papers available to all online.The role of sub-nanometric Ag species (on Fe, Mg and Ce modified TiO 2 materials) on catalytic CO oxidation is studied by several techniques in [1]. The observed phenomena cannot be explained only considering the 1-13 nm Ag particle size distributions measured by HRTEM; the existence of Ag species with size < 1 nm, non-visible in HRTEM, and their interaction with the supports, needs also to be taken into account.Silver and copper are reported as catalysts, in a new and efficient way, for the cycloaddition of propargyl-substituted dihydroisoindolin-1-one with arylnitrile oxides to produce novel 3,5-disubstituted isoxazoles of the ethyl-2-benzyl-3-oxo-1-((3-arylisoxazol-5yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylate type [2]. Yields are significantly improved with the presence of Cu I as catalyst compared to the uncatalyzed reaction, without changing the selectivity.Aroylhydrazone Cu(II) complexes in keto form are reported as catalysts for the peroxidative oxidation of cyclohexane to cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone, under mild conditions [3]. The activity exhibited by those complexes in the absence of any additive, is higher than that shown by other efficient Cu II systems reported in the literature.Copper is also used as a catalyst, deposited on different lanthanide-doped cerium oxides (Ce 0.5 Ln 0.5 O 1.75 , where Ln: Gd, La, Pr, Nd) for the oxidation of ethyl acetate, a harmful volatile organic compound [4]. The best catalytic performance was obtained for Cu/CeO 2 and Cu/Ce 0.5 Pr 0.5 O 1.75 samples. A strong correlation was found between the catalytic performance and the redox properties of the samples, in terms of reducibility and lattice oxygen availability.Gold incorporated on a mesoporous silica thin film is reported as a robust surface enhanced Raman scattering (SERS) and catalytically active substrate for the reduction of p-nitrophenol to p-aminophenol [6]. This material might offer a promising eco-friendly way for the product...

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Synthesis of Isoxazole and 1,2,3-Triazole Isoindole Derivatives via Silver- and Copper-Catalyzed 1,3-Dipolar Cycloaddition Reaction

Cited by 13 publications

References 53 publications

Synthesis of New Spirooxindole‐Fused Isoxazoline/Triazole and Isoxazoline/Isoxazole Derivatives from Three‐Component 1,3‐Dipolar Cycloaddition

Synthesis of New Spirooxindole‐Fused Isoxazoline/Triazole and Isoxazoline/Isoxazole Derivatives from Three‐Component 1,3‐Dipolar Cycloaddition

Design and Synthesis of New Tubulin Polymerization Inhibitors Inspired from Combretastatin A‐4: An Anticancer Agent

Special Issue: Coinage Metal (Copper, Silver, and Gold) Catalysis

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