Synthesis of some new pyridazin‐3‐one derivatives and their utility in heterocyclic synthesis

El-Mobayed, M.; Hussein, Ahmed; Mohlhel, Wafia M.

doi:10.1002/jhet.357

Cited by 9 publications

(5 citation statements)

References 7 publications

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“…The resulting precipitate was filtered to give compounds A1, A2. The measured melting points for A1 and A2 were in agreement with the literature (A1 found: 239-241 º C, A1 literature: 235-237 º C; A2: 263-265 º C) [14,21].…”

Section: Synthesis Of 6-(4-chloro/4-bromophenyl)-3(2h)-pyridazinone Asupporting

confidence: 89%

Studies on a novel series of 3(2H)-pyridazinones: Synthesis, molecular modelling, antimicrobial activity

Özdemi̇r¹,

Alagöz²,

Akdemir³

et al. 2019

jrp

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Efforts to develop new potent and effective antimicrobial compounds with lower side effects are important not only for controlling serious infections but also for cancer, surgical operations, and preventing possible infections which are related to other threats. Therefore, it is getting more important to develop new antibacterial and antifungal compounds with wide spectrum, systemic effect and lower side effects. In this study eight new 3(2H)pyridazinone derivatives were synthesized and their antimicrobial activities were evaluated by using broth microdilution method agains two Gr (+) (Staphylococcus aureus, Enterococcus faecalis), two Gr (-) bacteria (Pseudomonas aeruginosa, Escherichia coli) and three yeasts like fungi (Candida albicans, Candida krusei). Compound D2a had the best antibacterial activity among the synthesized compounds. All compounds were more effective against the fungus than the bacteria. In this study, we performed molecular modelling studies to provide in depth understanding of their CYP51 inhibition. Antifungal susceptibility tests against standard Candida spp. including C. albicans revealed D2aas highly active compound. The molecular docking studies showed similarities in binding interactions in active site gorges of the enzymes with known inhibitors, such as VT1, fluconazole.

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Section: Synthesis Of 6-(4-chloro/4-bromophenyl)-3(2h)-pyridazinone Asupporting

confidence: 89%

Studies on a novel series of 3(2H)-pyridazinones: Synthesis, molecular modelling, antimicrobial activity

Özdemi̇r¹,

Alagöz²,

Akdemir³

et al. 2019

jrp

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“…Oximes containing a carbonyl group at the γ-position easily cyclize to dihydrooxazines without the formation of side cyclic nitrones of the type 47 (Scheme ). − …”

Section: Synthesis Of Six-membered Cyclic Oxime Ethers 1 Andmentioning

confidence: 99%

“…Thus, carboxy-substituted oximes generated from the corresponding keto acids 54 and hydroxylamine can dehydrate to 3-aryl-substituted oxazinones 55 directly upon preparation (Scheme , eq 1), − under the action of sulfuric acid in a catalytic amount or upon treatment with dicyclohexylcarbodiimide. , Methyl esters of unsaturated acids 56 also easily cyclize to 1,2-oxazin-6-ones 57 as well (Scheme , eq 2). , This procedure allows one to synthesize oxazinones 57 from substituted furans 58 …”

Section: Synthesis Of Six-membered Cyclic Oxime Ethers 1 Andmentioning

confidence: 99%

Chemistry of Six-Membered Cyclic Oxime Ethers. Application in the Synthesis of Bioactive Compounds

2011

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CONTENTS 1. Introduction 5004 2. Synthesis of Six-Membered Cyclic Oxime Ethers 1 and 2 5005 2.1. [4 þ 2]-Cycloaddition Reactions 5005 2.2. Intramolecular Cyclization of γ-Functionalized Oximes 5009 2.3. Intramolecular Cyclization of Functionalized O-Substituted Hydroxylamines 5012 2.4. Synthesis of SCOE from N-O-Containing Heterocyclic Derivatives 5012 2.4.1. Synthesis of SCOE from Other 1,2-Oxazines 5012 2.4.2. Synthesis of SCOE from Isoxazolines and Five-Membered Cyclic Nitronates 5014 2.5. Other Methods 5014 3. Chemical Properties of SCOE 5016 3.1. Reduction of SCOE 5016 3.1.1. Reduction of SCOE to Tetrahydro-2H-1,2oxazines 5018 3.1.2. Reduction of SCOE with 1,2-Oxazine Ring-Opening 5020 3.1.2.1. Reduction of SCOE to 1,4-Amino Alcohols. 5020 3.1.2.2. Reduction of SCOE to Carbonyl Compounds. 5021 3.1.2.3. Reduction of SCOE to γ-Hydroxyoximes. 5022 3.1.3. Reduction Reactions of SCOE with 1,2-Oxazine Ring Contraction 5022 3.1.3.1. Reduction of SCOE to Pyrrolidines. 5022 3.1.3.2. Reduction of SCOE to N-Hydroxypyrrolidines. 5023 3.1.3.3. Reduction of SCOE to Pyrroles. 5024 3.1.3.4. Reduction of SCOE to Aziridines. 5025 3.1.3.5. Reduction of SCOE to Furan Derivatives. 5025 3.2. Addition Reactions to the CdN Double Bond of SCOE 5026 3.3. 1,2-Oxazine Ring-Opening in SCOE 5027 3.4. Deoximation of SCOE 5028 3.5. 1,2-Oxazine Ring Rearrangements in SCOE 5028 3.6. 1,2-Oxazine Ring Fragmentation Reactions in SCOE 5030 4. SCOE in the Synthesis of Natural Products and Biologically Active Compounds 5031 4.1. Synthesis of Amino Acids 5032 4.2. Synthesis of Polyhydroxylated Pyrrolidines 5033 4.3. Synthesis of Pyrrolizidine and Indolizidine Alkaloids and Their Analogs 5033 4.4. Synthesis of Biologically Active 2-Aryl-Substituted Pyrrolidines and Amines 5035 4.5. Synthesis of Other Natural Compounds 5036 5. Conclusion 5037 Author Information 5037 Biographies 5038 Acknowledgment 5038 References 5038

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“…Moreover, they show a marked increase in in vitro activity against Grampositive bacteria [5] and cancer [6]. These are used as key starting materials due to their high electrophilicity, where the β-aroyl acrylic acids react readily with nucleophiles, including nitrogen and sulfur nucleophiles, to afford either cyclic or normal Michael adducts depending on the nature of the attacking nucleophiles and the reaction medium (neutral, basic, acidic) and the Michael addition reaction may be utilized in tandem as efficient strategy for the construction of ring structures [7][8][9]. Therefore, this starting material has been used to prepare more interesting heterocyclic 1,5-benzothiazepine compounds having a substituent in the fused benzene ring, which may have diverse biological activities.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of 1,5-Benzothiazepines: Part 48: Single Pot Syntheses and Antimicrobial Studies of 8-Substituted 4-(2,4/2,5-disubstituted aryl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic Acids

Pant¹,

Yadav²

2017

Asian J. Chem.

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Two substituted acrylic acids, β-(2,4-dimethylbenzoyl) acrylic acid and β-(2,5-diisopropylbenzoyl) acrylic acid were reacted with six 5-substituted 2-aminobenzenethiols, in dry ethanol containing trifluroacetic acid to obtain ten new compounds, 8-substituted 4-(2,4-dimethylphenyl/2,5-diisopropylphenyl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic acids in 53-63 % yields. The products were characterized on the basis of micro analytical data and spectral analysis comprising IR, 1 H NMR and mass studies. All the synthesized compounds have been screened for their antimicrobial activity against the Gram-positive bacteria, Staphylococcus aureus and Gramnegative bacteria, Enterobacter cloacae, Klebsiella aerogenes and fungus, Candida albicans with respective reference compounds. Keywords: Acrylic acids, 5-Substituted 2-aminobenzenethiols, Antimicrobial activity.Asian Journal of Chemistry; Vol. 29, No. 10 (2017), 2221-2223 containing trifluoroacetic acid to obtain the final compounds in single step in 53-63 % yields. The purity of the final products was checked by TLC. The structures of the final products were ascertained by elemental and spectral analyses comprising IR, 1 H NMR and mass spectral studies. All the compounds 3a-l were evaluated for their antimicrobial activity, comprising antibacterial and antifungal.General procedure for the syntheses of 8-substituted 4-(2,4-dimethylphenyl/2,5-diisopropylphenyl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic acids (3a-l): To a solution of β-(2,4-dimethylbenzoyl/2,5-diisopropylbenzoyl) acrylic acid (1, 0.001 mol) in dry ethanol (5 mL) containing trifluoroacetic acid, was added the ethanolic solution of 5-substituted 2-aminobenzenethiols (2, 0.001mol) with continuous stirring. The reaction mixture after refluxing for 3-4 h followed by cooling, afforded the crude, which was filtered and crystallized from ethanol to give coloured crystals of the target compounds (3a-l).Antimicrobial activity: The antimicrobial activity of all newly synthesized compounds 8-substituted 2,3-dihydro-4-(2,4-dimethylphenyl/2,5-diisopropylphenyl)-1,5-benzothiazepine-2-carboxylic acids (3a-l), were carried out using paper disc method [11] against the Gram-positive bacteria Staphylococcus aureus and the Gram-negative bacteria Enterobacter cloacae, Klebsiella aerogenes and antifungal activity against the fungus, Candida albicans at the concentration of 200 µg/disc, with vancomycin and polymixin B and fluconazole as the reference drugs, respectively. The reference compounds were used to evaluate the activity in the form of activityScheme-I index. Zones of inhibition, exhibited by the reference and test compounds, were measured and compared to show relative activities in the form of activity index. The physical constants and the antimicrobial activity is given in Table-1. Detection method: All the reported melting points are uncorrected. Purity of the compounds were checked by TLC on glass plates coated with silica gel 'G' as absorbent, using benzene : ethanol : aq. ammonia (50 %) in the ratio 7:2:1 as so...

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Synthesis of some new pyridazin‐3‐one derivatives and their utility in heterocyclic synthesis

Cited by 9 publications

References 7 publications

Studies on a novel series of 3(2H)-pyridazinones: Synthesis, molecular modelling, antimicrobial activity

Studies on a novel series of 3(2H)-pyridazinones: Synthesis, molecular modelling, antimicrobial activity

Chemistry of Six-Membered Cyclic Oxime Ethers. Application in the Synthesis of Bioactive Compounds

Syntheses of 1,5-Benzothiazepines: Part 48: Single Pot Syntheses and Antimicrobial Studies of 8-Substituted 4-(2,4/2,5-disubstituted aryl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic Acids

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