Ultrasound‐Assisted Green Synthesis of 3,5‐Disubstituted Isoxazole Secondary Sulfonamides via One‐Pot Five‐Component Reaction using CaCl2/K2CO3 as Pre‐Catalyst in Water

Mahmoudi, Ayoub El; Tachallait, Hamza; Moutaoukil, Zakaria; Arshad, Suhana; Karrouchi, Khalid; Benhida, Rachid; Bougrin, Khalid

doi:10.1002/slct.202203072

Cited by 5 publications

(3 citation statements)

References 71 publications

(38 reference statements)

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“…The nitrile oxide was then trapped by the N ‐allyl‐saccharin 3 (1equiv.) prepared using our previously reported method 54 as a dipolarophile via the 1,3‐dipolar cycloaddition to form the 3,5‐disubstituted isoxazoline‐saccharin as expected intermediate 4a–f under ultrasound cavitation. Then, the obtained products 4a–f were reacted with non‐conjugated primary amines 5a–f (2 equiv.)…”

Section: Resultsmentioning

confidence: 99%

Green synthesis, characterization, and biochemical impacts of new bioactive isoxazoline‐sulfonamides as potential insecticidal agents against the Sphodroxia maroccana Ley

Mahmoudi

Fegrouche

Tachallait

et al. 2023

Pest Management Science

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BACKGROUNDSphodroxia maroccana Ley is a pest of cork oak crops that damages the roots of seedlings and can severely impair cork oak regeneration. Since the banning of carbosulfan and chlorpyriphos, which were widely used against the larvae of Sphodroxia maroccana because of their harmful impact on the environment, until now there has been no pesticide against these pests. Therefore, it is particularly urgent to develop highly effective insecticidal molecules with novel scaffolds. Isoxazolines are a class of insecticides that act on γ‐aminobutyric acid (GABA)‐gated chloride channel allosteric modulators. In this work, a green synthesis of novel 3,5‐disubstituted isoxazoline‐sulfonamide derivatives was achieved in water via ultrasound‐assisted four‐component reactions, and their insecticidal activities against fourth‐instar larvae of S. maroccana were evaluated.RESULTSMost of the tested compounds showed insecticidal activity compared to fluralaner as positive control and commercially available insecticide. Especially, the isoxazoline‐secondary sulfonamides containing halogens (Br and Cl) on the phenyl group attached to the isoxazoline, 6g (LC50 = 0.31 mg/mL), 6j (LC50 = 0.38 mg/mL), 6k (LC50 = 0.18 mg/mL), 6L (LC50 = 0.49 mg/mL), 6m (LC50 = 0.24 mg/mL), 6q (LC50 = 0.46 mg/mL), exhibited much higher larvicidal activity than fluralaner (LC50 = 0.99 mg/mL).CONCLUSIONNovel isoxazolines containing sulfonamide moieties were designed, synthesized and confirmed by two single‐crystal structures of 4e and 6q. Their bioassay results showed significant larvicidal activity with significant morphological changes in vivo. These results will lay the foundation for the further discovery and development of isoxazoline‐sulfonamide derivatives as novel crop protection larvicides of cork oak. © 2023 Society of Chemical Industry.

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Section: Resultsmentioning

confidence: 99%

Green synthesis, characterization, and biochemical impacts of new bioactive isoxazoline‐sulfonamides as potential insecticidal agents against the Sphodroxia maroccana Ley

Mahmoudi

Fegrouche

Tachallait

et al. 2023

Pest Management Science

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“…Today in the modern methodology used in the preparation of the amide using green chemistry, the synthetic procedure includes the reaction carried out in conditions water [25], microwave [26], ultrasound [27], electro synthesis [28].…”

Section: Beckmann Rearrangement Of Oximesmentioning

confidence: 99%

New Acetamide Derivatives of the COX-II Inhibitors-A Brief Review

Atrushi¹,

Ameen²,

Abachi³

2023

Arch Pharm Pract

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The most traditional and popular agents are non-steroidal anti-inflammatory drugs (NSAIDs). However, due to their side effects on different organs. In this review, several compounds created as acetamide derivatives to maintain their anti-inflammatory properties, selective COX-II inhibitors, are discussed. Numerous literature reviews have highlighted the significance of these anti-inflammatory heterocyclic compounds in treatments, taking into consideration the significance of this pharmacological class. Cyclooxygenase-II (COX-II) inhibitors can be used in a wide variety of applications thanks to the prodrug method. It plays a big part in drug development. Many researchers have created different prodrugs using acetamide molecules to adjust pharmacokinetic parameters, enhance organoleptic qualities, or increase chemical properties. A huge quantity of amide derivatives belonging to different classes of compounds exhibit cyclooxygenase-II inhibitors and mainly to treat arthritis, pain, menstrual camps, and colonic polyps, they used for relief of pain, fever, swelling, and tenderness. Finally, the nanoparticles of cyclooxygenase (II) inhibitors were used for improving the efficacy.

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“…Therefore, finding a green and efficient source for the synthesis of secondary sulfonamide derivatives should be a priority. Our research group has recently developed the synthesis of a new series of heterocyclic units bearing secondary sulfonamides using an eco-friendly protocol under ultrasound cavitation [12,13].…”

Section: Introductionmentioning

confidence: 99%

2-(N-allylsulfamoyl)-N-propylbenzamide

El mahmoudi,

Chkirate,

Mokhi

et al. 2023

Molbank

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In this work, a new compound, 2-(N-allylsulfamoyl)-N-propylbenzamide, has been synthesized via a tandem one-pot reaction under sonication. The rotational orientations of the allylsulfamoyl and the amide groups in the title molecule, C13H18N2O3S, are partly determined by an intramolecular N—H···O hydrogen bond. In the crystal, a layer structure is generated by N—H···O and C—H···O hydrogen bonds plus C—H···π (ring) interactions. A Hirshfeld surface analysis indicates that the most important contributions to crystal packing are from H···H (59.2%), H···O/O···H (23.5%), and H···C/C···H (14.6%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G (d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 5.3828 eV.

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Ultrasound‐Assisted Green Synthesis of 3,5‐Disubstituted Isoxazole Secondary Sulfonamides via One‐Pot Five‐Component Reaction using CaCl₂/K₂CO₃ as Pre‐Catalyst in Water

Cited by 5 publications

References 71 publications

Green synthesis, characterization, and biochemical impacts of new bioactive isoxazoline‐sulfonamides as potential insecticidal agents against the Sphodroxia maroccana Ley

Green synthesis, characterization, and biochemical impacts of new bioactive isoxazoline‐sulfonamides as potential insecticidal agents against the Sphodroxia maroccana Ley

New Acetamide Derivatives of the COX-II Inhibitors-A Brief Review

2-(N-allylsulfamoyl)-N-propylbenzamide

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