One-Pot Synthesis of Novel 2-(Thiazol-2-yl)-4,5-dihydropyridazin-3(2<i>H</i>)-one Derivatives Catalyzed by Activated KSF

Mahmoodi, Nosrat O.; Safari, Niloufar; Sharifzadeh, Bahman

doi:10.1080/00397911.2013.801077

Cited by 18 publications

(7 citation statements)

References 29 publications

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“…Continuing our studies of the synthesis of novel compounds bearing heteroatoms [31][32][33][34][35][36] here, synthesis of a new series of 2-(aryl or alkyl)-N-phenylhydrazine-1-carboxamide 1a-j via one-pot reaction is completed. The products 1a-j were obtained through the reaction of anthracene carbaldehyde 4g or cyclic aliphatics 4a-f, or aromatic ketones 4h-j with hydrazine hydrate and phenyl isocyante 5 in MeOH under reflux condition (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

et al. 2015

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New series of 2-(aryl or alkyl)-N-phenylhydrazine-1-carboxamides 1a-j were synthesized through one-pot reactions of aldehyde or ketones, hydrazine hydrate, and phenylisocyanate in MeOH. The structure of products was confirmed by Fourier transform infrared (FT-IR), proton nuclear magnetic resonance ( 1 H NMR), and 13 C NMR spectra. Minimum inhibitory concentration (MIC) of antibacterial activity of 1a-j was screened against five bacterial strains. Compound 1f showed antibacterial activity against Pseudomonas aeruginosa and Staphylococcus aureus.

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Section: Resultsmentioning

confidence: 99%

Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

et al. 2015

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“…In addition, the importance of pyridazinones in medicinal chemistry has increased in recent years thanks to their pharmacological properties, including anticancer (Yarden & Caldes, 2013), antihypertensive (Siddiqui et al, 2011), antibacterial (Akhtar et al, 2016), anti-HIV (Livermore et al, 1993), anti-inflammatory (Singh et al, 2017), antidepressant (Boukharsa et al, 2016), anti-convulsant (Partap et al, 2018) and cardiotonic (Costas et al, 2015) activities. Several pyridazinone-based products are already present in the pharmaceutical market such as Minaprine (Sotelo et al, 2003), Azanrinone (Mahmoodi et al, 2014), Indolidan (Abouzid et al, 2008) and Levosimendan (Archan & Toller, 2008).…”

Section: Chemical Contextmentioning

confidence: 99%

Polymorphism of 2-(5-benzyl-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl)acetic acid with two monoclinic modifications: crystal structures and Hirshfeld surface analyses

Daoui¹,

Baydere²,

Chelfi³

et al. 2020

Acta Cryst E

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Two polymorphs of the title compound, C19H16N2O3, were obtained from ethanolic (polymorph I) and methanolic solutions (polymorph II), respectively. Both polymorphs crystallize in the monoclinic system with four formula units per cell and a complete molecule in the asymmetric unit. The main difference between the molecules of (I) and (II) is the reversed position of the hydroxy group of the carboxylic function. All other conformational features are found to be similar in the two molecules. The different orientation of the OH group results in different hydrogen-bonding schemes in the crystal structures of (I) and (II). Whereas in (I) intermolecular O—H...O hydrogen bonds with the pyridazinone carbonyl O atom as acceptor generate chains with a C(7) motif extending parallel to the b-axis direction, in the crystal of (II) pairs of inversion-related O—H...O hydrogen bonds with an R 2 2(8) ring motif between two carboxylic functions are found. The intermolecular interactions in both crystal structures were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

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“…Encouraged by all of the above, as well as the limited studies on the synthesis of bis‐thiazoles in the literature, and in continuation of our ongoing research program on the synthesis of mono‐ and bis‐thiazoles and screening for their biological activities, we report in this paper the one‐pot semi‐five‐component, efficient, and rapid method for the synthesis of new bis‐thiazoles and screening otheir antibacterial and antioxidant activities.…”

Section: Introductionmentioning

confidence: 98%

Sequential one‐pot multicomponent synthesis of bis‐aminothiazols and evaluation of their antibacterial and antioxidant activities

Parvizi

Mahmoodi

Pirbasti

2018

J Chinese Chemical Soc

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A series of novel bis-thiazoles were synthesized through a one-pot semi-fivecomponent reaction of the prepared α-bisbromo ketones, aldehydes, and thiosemicarbazide in the presence of p-TsOH under reflux condition. Products were obtained in reasonable yields via an efficient, convenient, and simple setup. The inhibitory activity on bacterial growth of the products was studied against Gramnegative (Escherichia coli and Pseudomonas aeruginosa) and Gram-positive bacterial strains (Micrococcus luteus, Staphylococcus aureus) at different concentrations (25, 50, 100, and 200 μg/mL at 600 nm). Most of the products showed inhibitory activity at the concentration of 200 μg/mL. In addition, bis-thiazoles showeed high to moderate antioxidant activity using the diphenylpicrylhydrazyl (DPPH) method. Bis-thiazoles 6i and 6j showed higher antioxidant activity than vitamin C and vitamin E.

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One-Pot Synthesis of Novel 2-(Thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one Derivatives Catalyzed by Activated KSF

Cited by 18 publications

References 29 publications

Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

Polymorphism of 2-(5-benzyl-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl)acetic acid with two monoclinic modifications: crystal structures and Hirshfeld surface analyses

Sequential one‐pot multicomponent synthesis of bis‐aminothiazols and evaluation of their antibacterial and antioxidant activities

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