The Chemistry of Thienopyrimidines

Литвинов, В. П.

doi:10.1016/s0065-2725(06)92003-0

Cited by 36 publications

(5 citation statements)

References 165 publications

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“…The inhibitors molecules induce cell death by trapping the gyrase DNA complex, inducing oxidative damage, and preventing DNA replication. 4 Thienopyrimidines represent important chemical class in drug discovery due to vast range of pharmacological properties including antiallergic, 5 antiviral, [6][7] anti-in-flammatory, [8][9][10][11][12] analgesic, [13][14] antispasmodic, antibacterial, [14][15] antifungal, 16 antimicrobial, [17][18][19][20][21] antidiabetic, 22 antioxidant, 23 antitumor, [24][25][26][27][28][29] antipsychotic 30 etc. This useful activity of thienopyrimidine generates our interest in developing a tool for screening novel thienopyrimidine analogs are promise antibacterial agent.…”

Section: Introductionmentioning

confidence: 99%

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Ouassaf¹,

Belaidi

Khamouli³

et al. 2021

ACSi

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The discovery of antibacterials is considered one of the greatest medical achievements of all time. In this work, a combination of three computational analyzes: 3D-QSAR, molecular docking and ADME evaluation were applied in thienopyrimidine derivatives intended toward gram-positive bacterium Staphylococcus aureus. The validity of 3D-QSAR model was tested with a set of data which is divided into a training and a test set. The two models constructed (CoMFA and CoMSIA) show good statistical reliability (q2 = 0.758; r2 = 0.96; r2pred = 0.783) and (q2 = 0.744; r2 = 0.97; r2pred = 0.625) respectively. In addition, docking methods were applied to understand the structural features responsible for the affinity of the ligands in the binding of S. aureus DNA gyrase. Drug likeness and ADME analysis applied in this series of new proposed compounds, have shown that the five lead molecules would have the potential to be effective drugs and could be used as a starting point for designing compounds against Staphylococcus aureus.

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Section: Introductionmentioning

confidence: 99%

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Ouassaf¹,

Belaidi

Khamouli³

et al. 2021

ACSi

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“…Thieno[2,3-d]pyrimidines are purine bioisosteres coming to the center of interest due to their high structural diversity and well-documented spectrum of biological activity (for reviews, see refs − ). Much less is known on the preparation and reactions of partially saturated thieno[2,3-d]pyrimidines. − To study the reactivity of the prepared ADHTs 6 under Mannich conditions, their behavior upon treatment with a series of primary amines and HCHO was examined here.…”

Section: Resultsmentioning

confidence: 99%

2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines

et al. 2021

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trans-2-Amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles were prepared either by the reaction of 3-aryl-2-cyanothioacrylamides with α-thiocyanatoacetophenone or by the Michael-type addition of cyanothioacetamide to α-bromochalcones followed by intramolecular cyclization. The mechanism of the first reaction was studied using high-level quantum chemical calculations. Density functional theory (DFT) studies were carried out to determine the mechanism of the first reaction. A new approach toward the construction of the thieno[2,3-d]pyrimidine core system was demonstrated by the reaction of the prepared dihydrothiophenes with HCHO and RNH2 under noncatalyzed Mannich conditions.

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“…[21][22][23] However, the presence of both nitrile and secondary amine functions in the same molecule is efficiently used in producing hetero fused thiénopsmidines compounds. [24][25][26] Following to the previously reported method, [27][28][29] we synthesized the starting material 3-cyano-2-aminothiophenes 1a-b, from a One pot modified Gewald reaction of cyclohexanone with activated nitriles that have an active methylene group, and sulfur is particularly simple and rich in possibilities in the presence of morpholine as basic catalyst under reflux ethanol (EtOH) (Table 2).…”

Section: Synthesis Of 2-aminothiophenes 1a-bmentioning

confidence: 99%

“…[18] The heterocyclic annulated pyrimidine, such as thieno [2, 3-b] pyrimidine derivatives, occupy a special place and have frequently attracted a great deal of interest of chemists researchers. [19] Due to their remarkable applications in different disciplines, identified such as potent anti-cancer, [20] ant diabetic, [21] anti-hypertensive [22] and prevention of cartilage destruction in particular diseases, [23] while they also used in the fabrication of light-emitting diodes in material science, fungicides, [24] herbicides, [25] and insecticides, [26] and have other interesting pharmacological properties (Scheme 1). [27] Owing to their great importance and utility, they encourage many researchers to plan, discover and design new molecular systems [19] which offers some of the greatest hope.…”

Section: Introductionmentioning

confidence: 99%

Green catalyst access to thieno [2, 3‐b] pyridines derivatives

Mehaoui

Boudjema

Kibou

et al. 2023

Journal of Heterocyclic Chem

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The current study focuses on the use of tungstovanadophosphoric heteropoly acid H4PW11VO40·8 H2O (PVW) with Keggin structure and supported on acid activated (PVW/AAM) in the synthesis of new substituted Thieno [2, 3‐b] pyridines derivatives. The suggested protocol is an easy, environmentally friendly method for synthesis of thieno [2,3‐b] pyrimidine derivatives obtained from 3‐cyano‐2‐aminothiophene as building blocks under solvent‐free reactions condition. Excellent product yields of substituted Thieno [2, 3‐b] pyridine derivatives (60%–97%) were achieved using the synthesized PVW/AAM catalyst. The current processes provide benefits including a quicker reaction time, an easy set‐up, and high yields. Spectroscopic data (IR, +H and 13C NMR spectra) have revealed the structural details of all target compounds. The catalyst was characterized by X‐ray diffraction, BET and Fourier‐transformed infrared spectroscopy. X‐ray diffraction showed that PVW was correctly incorporated on an acid activated clays support. In comparison to the parent, Tungstovanadophosphoric acid, the PVW supported acid activated montmorillonite provided increased Lewis acid site density, redox characteristics, and surface area. Due to the recoverability of heterogeneous catalysts, the heterogenization of homogeneous catalysts is very attractive. In addition, the produced catalysts can be simply removed from the reaction system and reused six times more effectively.

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The Chemistry of Thienopyrimidines

Cited by 36 publications

References 165 publications

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines

Green catalyst access to thieno [2, 3‐b] pyridines derivatives

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