A New Route to 2,4,6‐Trisubstituted‐6H‐1,3‐oxazines.

Kidwai, Mazaahir; Thakur, Ravindra Singh; Mohan, Richa

doi:10.1002/chin.200515150

Cited by 6 publications

(6 citation statements)

References 1 publication

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“…[4] Barbituric acid derivatives have various biological properties such as sedative-hypnotic, antimicrobial, antifungal, anticancer, anticonvulsant, and anti-urease properties. [5][6][7][8][9][10] However, another important scaffold in designing new bioactive compounds is the 1,2,3-triazole ring. [11] There are several reports in the literature concerning urease inhibitory activity of barbituric acid derivatives and 1,2,3-triazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

New 1,2,3‐triazole–(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation

Asgari

Azizian

Montazer

et al. 2020

Archiv der Pharmazie

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A new series of 1,2,3‐triazole–(thio)barbituric acid hybrids 8a–n was designed and synthesized on the basis of potent pharmacophores with urease inhibitory activity. Therefore, these compounds were evaluated against Helicobacter pylori urease. The obtained result demonstrated that all the synthesized compounds, 8a–n, were more potent than the standard urease inhibitor, hydroxyurea. Moreover, among them, compounds 8a, 8c–e, 8g,h, and 8k,l exhibited higher urease inhibitory activities than the other standard inhibitor used: thiourea. Docking studies were performed with the synthesized compounds. Furthermore, molecular dynamic simulation of the most potent compounds, 8e and 8l, showed that these compounds interacted with the conserved residues Cys592 and His593, which belong to the active site flap and are essential for enzymatic activity. These interactions have two consequences: (a) blocking the movement of a flap at the entrance of the active site channel and (b) stabilizing the closed active site flap conformation, which significantly reduces the catalytic activity of urease. Calculation of the physicochemical and topological properties of the synthesized compounds 8a–n predicted that all these compounds can be orally active. The ADME prediction of compounds 8a–n was also performed.

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Section: Introductionmentioning

confidence: 99%

New 1,2,3‐triazole–(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation

Asgari

Azizian

Montazer

et al. 2020

Archiv der Pharmazie

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“…In addition, BA and TBA exhibit a wide range of biological activities, including antiepileptic, anticancer, antioxidant, anticonvulsant, immunomodulatory, gelatinase‐inhibiting, HIV integrase‐inhibiting, antifungal, antiviral, tyrosinase‐inhibiting, anti‐inflammatory, and antidiabetic effects. BA and TBA derivatives have also been evaluated for antimicrobial activity . 5‐Benzylidene BA and TBA show antibacterial activity, as well as an inhibitory effect against mushroom tyrosinase .…”

Section: Introductionmentioning

confidence: 99%

Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity

et al. 2018

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Thiobarbituric acid (TBA) has been considered a privileged structure for developing antimicrobial agents. Diversity was obtained at positions N and at C5 through acylation, Schiff base formation, Knoevenagel condensation, and thioamide and enamine formation. The present work describes the synthesis of small libraries based on the TBA moiety and above-mentioned reactions. Preliminary antimicrobial activity screening of the prepared compounds against selected bacteria (both Gram-positive and -negative) showed the best results for the Boc-Phe-TBA derivative. These results could be useful for designing and building libraries based on other amino acids with distinct protecting groups.

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“…Increasing attention for environmental protection during the last decades has led both modern academic and industrial groups to develop chemical processes with the maximum yield and minimum cost while using non-toxic reagents, solvents and catalysts (1). Microwave (MW) synthesis represents one of the important dimensions of modern chemistry attracting a considerable amount of attention (2).…”

Section: Introductionmentioning

confidence: 99%

Studies on chromium(III) complexes with active nitrogen, oxygen and sulfur donor ketimines synthesized under microwave conditions

Shrivastava

Fahmi

Singh

2010

Journal of Sulfur Chemistry

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Heterocyclic ketimines, 1-(2-furanyl)ethanonehydrazincarbothioamide (L 1 H), 1-(2-furanyl)ethanonehydrazincarboxamide (L 2 H), 1-(2-thienyl)ethanone hydrazincarbothioamide (L 3 H) and 1-(2-thienyl) ethanonehydrazincarboxamide (L 4 H), were prepared by the condensation of thiosemicarbazide and semicarbazide hydrochloride (in the presence of sodium acetate) in ethanol with the respective ketones by using microwave as well as conventional methods. Chromium(III) complexes have been prepared by mixing CrCl 3 · 6H 2 O in 1:1 and 1:2 molar ratios with monobasic bidentate ketimines. The authenticity of the ligands and their complexes has been established by elemental analyses, melting point determinations, molecular weight determinations, EPR, infrared and UV spectral and X-ray powder diffraction studies. These studies showed that the ligands coordinated to the metal atom in a monobasic bidentate mode, coordinating through the nitrogen and sulfur/oxygen donor system. Thus, an octahedral environment around the metal atoms has been proposed. The growth-inhibiting potential of the ligands and complexes has been assessed against a variety of fungal and bacterial strains.

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A New Route to 2,4,6‐Trisubstituted‐6H‐1,3‐oxazines.

Abstract: A New Route to 2,4,6-Trisubstituted-6H-1,3-oxazines. -Compared to conventional heating the microwave assisted condensation gives the desired compounds such as (III) in higher yields and in a shorter reaction time. -(KIDWAI*, M.; THAKUR, R.; MOHAN, R.; Bull. Chem.

Cited by 6 publications

References 1 publication

New 1,2,3‐triazole–(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation

New 1,2,3‐triazole–(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation

Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity

Studies on chromium(III) complexes with active nitrogen, oxygen and sulfur donor ketimines synthesized under microwave conditions

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