ChemInform Abstract: Synthesis of 2‐(2′‐Thenyl)‐3,1‐(4H)‐benzoxazin‐4‐one and Its Reactions with Different Nucleophiles.

El-Khamry, A. A.; Elnagdy, Sherif M.; Shaban, M. E.

doi:10.1002/chin.198906184

Cited by 3 publications

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“…Occasionally the reaction stops at the acyclic esters of 3-(2-acylaminophenyl)-3-oxopropionic acid [3].Proceeding from this, it seemed of interest to study the behavior of 2-ethoxycarbonylmethyl-4H-3,1-benzoxazin-4-one (1) under the described reaction conditions. Interest in such a family of investigations is caused, primarily, by the fact that the given acylanthranil itself contains an active methylene group, affording the possibility of the occurrence of more profound, occasionally unexpected, heterocyclizations [4][5][6][7].…”

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confidence: 97%

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4-Hydroxy-2-quinolones. 112. Reaction of 2-ethoxycarbonylmethyl-4H-3,1-benzoxazin-4-one with active methylene compounds

Украинец

Сидоренко

Gorokhova

et al. 2007

Chem Heterocycl Compd

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Keywords: 4H-3,1-benzoxazin-4-one, 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides, active methylene compounds.Under the action of active methylene compounds (acetoacetic, cyanoacetic, or malonic esters) in dry pyridine 2-substituted 4H-3,1-benzoxazin-4-ones (acylanthranils) usually recyclize into 2-R-4-oxo-3,4-dihydroquinoline-3-carboxylates [2]. Occasionally the reaction stops at the acyclic esters of 3-(2-acylaminophenyl)-3-oxopropionic acid [3].Proceeding from this, it seemed of interest to study the behavior of 2-ethoxycarbonylmethyl-4H-3,1-benzoxazin-4-one (1) under the described reaction conditions. Interest in such a family of investigations is caused, primarily, by the fact that the given acylanthranil itself contains an active methylene group, affording the possibility of the occurrence of more profound, occasionally unexpected, heterocyclizations [4][5][6][7].With the highly nucleophilic carbanion generated from malononitrile, benzoxazinone 1 reacts similarly with isatoic anhydride [8], i.e. the acylmalononitrile 2 formed initially is cyclized into the aminoquinolone 3. However, to isolate it was unsuccessful since under the conditions of the synthesis, boiling pyridine, the amino group is subject to intramolcular acylation with the formation of 1-hydroxy-3,6-dioxo-4,6-dihydro-3H-pyrimido[1,2-a]quinoline-5-carbonitrile (4).A completely different picture is observed on using acetoacetic, cyanoacetic, and malonic esters. In the first two cases the reaction products unexpectedly proved to be 2-ethoxycarbonyl-(5) and the 2-carboxy-(6) anilides of 1H-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid, and in the latter case the N,N'-di-2-carboxyanilide of malonic acid (7). The structures of the obtained compounds were confirmed by 1 H NMR and mass spectra, and also by a contrary synthesis, by amidation of 1H-3-ethoxycarbonyl-4-hydroxy-2-oxoquinoline (8) with ethyl anthranilate and anthranilic acid respectively or thermolysis of ethyl ester of 2-carboxymalonanilic acid (9).

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confidence: 97%

“…Occasionally the reaction stops at the acyclic esters of 3-(2-acylaminophenyl)-3-oxopropionic acid [3].…”

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confidence: 99%

4-Hydroxy-2-quinolones. 112. Reaction of 2-ethoxycarbonylmethyl-4H-3,1-benzoxazin-4-one with active methylene compounds

Украинец

Сидоренко

Gorokhova

et al. 2007

Chem Heterocycl Compd

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“…For this purpose, salicylaldehyde was converted to its sulfonate derivatives by using various sulfonyl chlorides according to the method reported previously. [ 25 ] Hydrazide derivatives of the anthranilic acid (F1−5) were synthesized in two steps starting from methyl anthranilate (methyl‐2‐amino benzoate) according to the method given by El Khamry et al [ 26 ] Finally, the target hydrazone analogues (1−15) were synthesized with good yields (93−98%) from the reactions of the compounds (A1−3) with the compounds (F1−5) , separately (Figure 1). The structures of the novel compounds were characterized with FTIR, 1 H NMR, 13 C NMR, and HRMS spectroscopic methods.…”

Section: Resultsmentioning

confidence: 99%

“…were synthesized in two steps starting from methyl anthranilate (methyl-2-amino benzoate) according to the method given by El Khamry et al [26] Finally, the target hydrazone analogues (1−15) were synthesized with good yields (93−98%) from the reactions of the compounds (A1−3) with the compounds (F1−5), separately (Figure 1).…”

Section: Chemistrymentioning

confidence: 99%

Novel hydrazones derived from anthranilic acid as potent cholinesterases and α‐glycosidase inhibitors: Synthesis, characterization, and biological effects

Tokalı,

Taslimi,

Taskin‐Tok

et al. 2023

J Biochem & Molecular Tox

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N‐substitued anthranilic acid derivatives are commonly found in the structure of many biologically active molecules. In this study, new members of hydrazones derived from anthranilic acid (1−15) were synthesized and investigated their effect on some metabolic enzymes such as acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α‐glycosidase (α‐Gly). Results indicated that all the molecules exhibited potent inhibitory effects against all targets as compared to the standard inhibitors, revealed by IC50 values. Ki values of compounds for AChE, BChE, and α‐Gly enzymes were obtained in the ranges 66.36 ± 8.30–153.82 ± 13.41, 52.68 ± 6.38–113.86, and 2.13 ± 0.25–2.84 nM, respectively. The molecular docking study was performed for the most active compounds to the determination of ligand–enzyme interactions. Binding affinities of the most active compound were found at the range of –9.70 to –9.00 kcal/mol for AChE, –11.60 to –10.60 kcal/mol for BChE, and −10.30 to −9.30 kcal/mol for α‐Gly. Molecular docking simulations showed that the novel compounds had preferential interaction with AChE, BChE, and α‐Gly. Drug‐likeness properties and ADMET (absorption, distribution, metabolism, excretion, and toxicity) analyzes of all synthesized compounds (1−15) were estimated and their toxic properties were evaluated as well as their therapeutic properties. Moreover, molecular dynamics simulations were carried out to understand the accuracy of the most potent derivatives of docking studies.

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“…Media: Nutrient agar and Potato Dextrose Agar [6,7] plates were used for bacterial and fungal organisms respectively.…”

Section: Methodsmentioning

confidence: 99%

Studies on Some Benzoxazine-4-one Derivatives with Potential Biological Activity

Habib¹,

Hassan²

2012

AJOC

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2-(4-Toluenesulphonyloxy phenyl)-3,1-benzoxazine-4-one 2 was prepared and reacted with some nitrogen nucleophiles, e.g., ammonia, o-phenylendiamine, some heterocyclic amines, hydrazine hydrate and hydroxylamine hydrochloride and sulphur nucleophile, e.g., phosphorous pentasulphide. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. All new prepared compounds were subjected to antimicrobial activity evaluation where compounds, 8, 9, 10 and 18 exhibited good activities against Bacillus Thuringenesis and 5, 10, 11, 14, 15, 17 and 18 exhibited good activities against Klebseilla Pneumonia. On the other hand, the results for antifungal activities revealed that, compounds 5, 6, 7, 16 and 17 exhibited good activities against Trichoderma Herzianum and Trichoderma Virdi.

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ChemInform Abstract: Synthesis of 2‐(2′‐Thenyl)‐3,1‐(4H)‐benzoxazin‐4‐one and Its Reactions with Different Nucleophiles.

Abstract: The thenylbenzoxazinone (III) is cleaved with the amines (II) or hydrazine hydrate (IV) to form the anthranilamides (I) and the carbohydrazide hydrazone (V).

Cited by 3 publications

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4-Hydroxy-2-quinolones. 112. Reaction of 2-ethoxycarbonylmethyl-4H-3,1-benzoxazin-4-one with active methylene compounds

4-Hydroxy-2-quinolones. 112. Reaction of 2-ethoxycarbonylmethyl-4H-3,1-benzoxazin-4-one with active methylene compounds

Novel hydrazones derived from anthranilic acid as potent cholinesterases and α‐glycosidase inhibitors: Synthesis, characterization, and biological effects

Studies on Some Benzoxazine-4-one Derivatives with Potential Biological Activity

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