An efficient and green synthesis of phthalide-fused pyrazole and pyrimidine derivatives

Motamedi, Anahita; Sattari, Elahe; Mirzaei, Peiman; Armaghan, Mahsa; Bazgir, Ayoob

doi:10.1016/j.tetlet.2014.02.101

Cited by 21 publications

(6 citation statements)

References 26 publications

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“…The yield of the first step was between 70 and 88%. 24 , 25 At first, a Knoevenagel reaction occurs between the aldehyde group of 2-formyl benzoic acid 1 and barbiturate derivatives 2 . This leads to forming a double bond conjugated to the carbonyl groups of the barbiturates 2 .…”

Section: Resultsmentioning

confidence: 99%

“…In the first step, 2-formyl benzoic acid 1 was reacted with barbiturate derivatives 2 in water or 50% ethanol as the solvent to get compounds 3a–c . The yield of the first step was between 70 and 88%. , At first, a Knoevenagel reaction occurs between the aldehyde group of 2-formyl benzoic acid 1 and barbiturate derivatives 2 . This leads to forming a double bond conjugated to the carbonyl groups of the barbiturates 2 .…”

Section: Resultsmentioning

confidence: 99%

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Isoindolin-1-ones Fused to Barbiturates: From Design and Molecular Docking to Synthesis and Urease Inhibitory Evaluation

et al. 2022

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Helicobacter pylori -induced ulcers and gastric cancer have been one of the main obstacles that the human community has ever struggled with, especially in recent decades. Several different attempts have been made to eradicate this group. One of the most widely used attempts is to inhibit the critical enzyme that facilitates its survival, the urease enzyme. Therefore, in this study, isoindolin-1-ones fused to barbiturates were designed, synthesized, and evaluated for their in vitro urease inhibitory activity as novel inhibitors for the urease enzyme. The synthesis route consisted of two steps. These steps increased the yield rate and decreased the percentage of byproducts while approaching green chemistry using ethanol and water as green solvents and microwave irradiation instead of conventional methods. In vitro urease inhibitory results indicated that all the compounds had higher inhibitory activity than the standard inhibitor, thiourea, and compound 5b proved to be the most potent inhibitor (IC 50 = 0.82 ± 0.03 μM). A molecular docking study was performed to understand the interaction between compounds 5a–n and Jack bean urease enzyme. The results of the molecular docking study were also in harmony with the in vitro results, which are discussed in detail later in this study.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Isoindolin-1-ones Fused to Barbiturates: From Design and Molecular Docking to Synthesis and Urease Inhibitory Evaluation

et al. 2022

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“…27,28 It was anticipated that by fusing two different heterocyclic rings on the same scaffold could lead to hybrid molecules with more potent biological activities as compared to the individual molecules. 29 This particular concept is further extended in this manuscript.…”

Section: Introductionmentioning

confidence: 82%

Concise strategy for diastereoselective annulation to afford fused [5:7] oxazepanone γ-lactams

Rashid¹,

Mohammat²,

Mansor³

et al. 2021

Arkivoc

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A series of novel potentially biologically active fused [5:7] oxazepanone γ-lactams were synthesized and described. A series of functional group transformations, namely amination, syn-hydrogenation and intramolecular annulation reactions were used to obtain the [5:7] oxazepanone γ-lactams in reasonable yields. In the diastereoselective fused-annulation for the formation of the secondary ring, steric constrain and cisgeometrical configuration of C-3 and C-4 substituents were observed as the predetermined factors. These ring annulations were purposely constructed to suit the physicochemical enhancement of the biological activity of the title compounds via SAR study of γ-lactams.

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“…In synthesis water have specific role because it is a green solvent and having tremendous application such as easily available, nontoxic, environmentally and economically friendly, therefore Anahita Motamedi et al [33] used water for synthesis of phthalide-fused pyrazole (10) and pyrimidine derivatives, without catalyst. This protocol is very greener approach for synthesis that reduces consumption of toxic solvents and eliminate production of hazardous waste material because there is no catalyst and organic solvents used in this synthesis.…”

Section: Aqueous Medium Synthesismentioning

confidence: 99%

Section: All Green Approaches For Pyrazole Synthesismentioning

confidence: 99%

Greener and Environmentally Benign Methodology for the Synthesis of Pyrazole Derivatives

Sapkal¹,

Kamble²

2020

ChemistrySelect

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Pyrazole and its derivatives are one of the interesting heterocyclic compounds among the other because it has tremendous important bio-medical applications such as anticancer, antimalarial, antimicrobial, antifungal, antitubercular and antihelishmanial. Synthesis of pyrazoles by synthetic route requires harsh reaction conditions such as organic solvent, high temperature, require large time that consume more energy which increase final cost of the synthesis of pyrazoles. Therefore researchers be aware about synthesis and give more attention towards to develop a greener as well as economically favorable method for synthesis of pyrazoles such as microwave irradiation, ultra-sonication assisted, reaction at room temperature, solvent and catalyst free and use of universal solvent that is aqueous medium these techniques are environmentally friendly as well as cost effective. Therefore, these review highlights the greener methodologies for the synthesis of pyrazoles, which are good alternative for synthetic methods that sustains green principles.

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An efficient and green synthesis of phthalide-fused pyrazole and pyrimidine derivatives

Cited by 21 publications

References 26 publications

Isoindolin-1-ones Fused to Barbiturates: From Design and Molecular Docking to Synthesis and Urease Inhibitory Evaluation

Isoindolin-1-ones Fused to Barbiturates: From Design and Molecular Docking to Synthesis and Urease Inhibitory Evaluation

Concise strategy for diastereoselective annulation to afford fused [5:7] oxazepanone γ-lactams

Greener and Environmentally Benign Methodology for the Synthesis of Pyrazole Derivatives

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