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Ryng, Stanisław; Głowiak, Tadeusz

doi:10.1023/a:1022464225693

Cited by 21 publications

(13 citation statements)

References 5 publications

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“…The quantum chemical calculations were performed for the structures, where the amide oxygen was connected by the hydrogen bond with amine nitrogen (Z isomer), because it was found, for many other isoxazole derivatives by X-Ray study, that such structures are favorable [15,16] .…”

Section: Qsar Analysismentioning

confidence: 99%

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

Ryng¹,

Zimecki

Fedorowicz

et al. 2001

Arch. Pharm. Pharm. Med. Chem.

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Section: Qsar Analysismentioning

confidence: 99%

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

Ryng¹,

Zimecki

Fedorowicz

et al. 2001

Arch. Pharm. Pharm. Med. Chem.

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“…The physical constants are summarized and presented in Table 8. To 3.2 mmol of 5-amino-3-methylisoxazole-4-carboxylic acid hydrazide [28,29] dissolved in 10 ml of isopropanol, 4.8 mmol of aldehyde or ketone was added. The solution was stirred and heated for 2 h. At the end of reaction (controlled in a TLC), the solution was cooled.…”

Section: Methodsmentioning

confidence: 99%

Structure/Activity Investigations of 5‐Substituted 3‐Methylisoxazole[5, 4‐d]1, 2, 3‐triazin‐4‐one Derivatives

Jezierska

Mączyński

Koll

et al. 2004

Archiv der Pharmazie

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The series of 5-substituted 3-methylisoxazole[5, 4-d]1, 2, 3-triazin-4-one derivatives was obtained by diazotization of 5-amino-3-methylisoxazol-4-carboxylic acid hydrazide. The immunological activity of these compounds was investigated experimentally in several in vitro and in vivo assays in mice and human models. In the next step, quantum-chemical investigations were performed using density functional theory with the B3LYP hybrid exchange-correlation energy functional and 6-31G(d, p) basis set. The Polarizable Continuum (SCRF/PCM) solvent model was also taken into account in order to show solvent influence on electron density and electrostatic potential around the exemplary molecules. Correlations between molecular structure and biological properties were found using a stepwise selection of scales for the multiple linear regression (MLR).

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“…Ureido derivatives of 5-amino-3-methylisoxazole-4-carboxylic acid were found to have a significant antileukemic activity [18]. Structure-activity relationship (SAR) studies of 5-methyl-3substituted phenylisoxazole-4-carboxamides revealed that they are potent antagonists for secretagogue receptors [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions

Ramana

Reddy

2011

Eur. J. Chem.

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KEYWORDSThe synthesis of series of 3-aryl-4-dihydrooxazolyl-5-methyl trisubstituted isoxazoles (VI) is reported, both under thermal and microwave conditions starting from various benzaldehydes (I). Benzaldehydes undergo oximation with hydroxylamine hydrosulphate to provide oximes that upon chlorination, followed by condensation with methylacetoacetate, resulted in the formation of esters. Hydrolysis of the esters to acids followed by treatment with PCl5, resulted in the formation of acid chlorides (III) that upon reaction with hydroxyamines, gave N-βhydoxyalkyl amides (IV). These on further reaction with SOCl2, followed by cyclization with 2 N NaOH provided oxazoline substituted isoxazoles (VI) in good yields. The conversion acid chlorides (III) to isoxazoles (VI) was also achieved by microwave irradiation in moderate to excellent yields, with shorter reaction times compared to the conventional thermal method. Isoxazole EthanolamineMicrowave irradiation Dihydrooxazoline Conventional Oximation

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Cited by 21 publications

References 5 publications

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

Structure/Activity Investigations of 5‐Substituted 3‐Methylisoxazole[5, 4‐d]1, 2, 3‐triazin‐4‐one Derivatives

Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions

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