5. Chemiluminescent organic compounds. Part II. The effect of substituents on the closure of phthalhydrazides to 5- and 6-membered rings

Drew, H. D. K.; Pearman, F. H.

doi:10.1039/jr9370000026

Cited by 39 publications

(18 citation statements)

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“…3-Hydroxyphthalimide was converted into 5-hydroxyphthalazine-1,4-dione by refluxing with aqueous hydrazire according to Drew & Pearman (1937). The hydroxy-cempound was recrystallized from a large volume of hot water to give almost white rods, melting point (m.p.)…”

Section: Methodsmentioning

confidence: 99%

“…The amino-compound was then converted into the 4-hydroxyphthalimide, m.p. 288 to 2900 C, by diazotization and boiling as described by Drew & Pearman (1937) for the preparation of the 3-hydroxy-isomer. The 4-hydroxy-compound was converted by hydrazinolysis to 6-hydroxyphthalazine-1,4-dione, which was obtained from hot water as white crystals, m.p.…”

Section: Methodsmentioning

confidence: 99%

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The Metabolism of Thalidomide: The Fate of Thalidomide and Some of Its Hydrolysis Products in Various Species

Schumacher

Smith

1965

British Journal of Pharmacology and Chemotherapy

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When thalidomide is administered orally to animals, only a small amount of the unchanged drug is excreted in the urine (for example, Beckman, 1962). The major portion of the compound is broken down and excreted as transformation products. After administration of the drug to man, rats and rabbits, Smith, Williams & Williams (1962) isolated 4-phthalimidoglutaramic acid from rabbit urine and detected it in human and rat urine. They also noted the presence in the urine of a fluorescent metabolite which they considered to be related to 3-hydroxyphthalic acid. Using [14C]-thalidomide, Faigle, Keberle, Riess & Schmid (1962) showed that the urine of dogs given thalidomide contained 2-and 4-phthalimidoglutaramic acid, 2-phthalimidoglutaric acid, a-(o-carboxybenzamido)glutarimide, 2-(o-carboxybenzamido)glutaric acid, phthalic acid and small amounts ofunchanged thalidomide, whilst the faeces contained only unchanged thalidomide.In order to emphasize the complexity of the problem of identifying the metabolites of thalidomide it should be pointed out that there are twelve possible hydrolysis products of (±)-thalidomide of which eleven can occur in (+)-and (-)-forms. The number of possible optically active products, including (+)-and (-)-thalidomide, is thus twenty-four. If thalidomide is hydroxylated in vivo, this could occur in the 3-or 4-position of the aromatic ring and possibly in three different positions (3', 4' and 5') in the glutarimide ring (see formula). Disregarding hydroxylation of the glutarimide ring and considering only the hydroxylation of the aromatic ring, there are twelve 3-hydroxy-and twelve 4-hydroxy-metabolites possible, and twenty-two of these can occur in (+)-and (-)-forms, the two compounds not containing an optically active carbon atom being 3-and 4-hydroxy-Q) NC H2 H phthalic acids. The number of possible metabolites of thalidomide is thus very large, for if any racemic metabolite underwent resolution the possible number of metabolites would be well over 100. In the present paper we describe the isolation and detection of some fifteen urinary metabolites and prove that rabbit urine contains derivatives of 3-and 4-hydroxyphthalic acid.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

The Metabolism of Thalidomide: The Fate of Thalidomide and Some of Its Hydrolysis Products in Various Species

Schumacher

Smith

1965

British Journal of Pharmacology and Chemotherapy

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“…Also when chemiluminescence was measured vs. the amount of authentic 3-hydroxyphthalic hydrazide (10 pmol-10 nmol) a linear response was obtained, Figure 3. [37]. Mean values of five measurements with a standard deviation <5% are presented in the figure.…”

Section: Figure 1 Reduction Of Adsorbed Oxygen and Formation Of Ros mentioning

confidence: 99%

“…In most experiments, the concentration of phthalic hydrazide was 0.5 mM. 3-Hydroxyphthalic hydrazide (2,3-dihydro-5-hydroxy-1,4-phthalazinedione) was synthesized as described by Drew and Pearman [37].…”

Section: Materials and Preparationsmentioning

confidence: 99%

Generation of Free OHaq Radicals by Black Light Illumination of Degussa (Evonik) P25 TiO2 Aqueous Suspensions

Liao¹,

Reitberger

2013

Catalysts

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This work demonstrates how formation of strongly chemiluminescent 3-hydroxyphthalic hydrazide by hydroxylation of non-chemiluminescent phthalic hydrazide can be applied as a selective reaction probe to obtain information on authentic hydroxyl radical, i.e.,• OH aq , formation, in black light illuminated Degussa P25 TiO 2 aerated suspensions in the pH range from 3 to 11. The • OH aq formation was found to be strongly pH dependent. At alkaline pH, the apparent quantum efficiency of • OH aq formation was estimated to be at the ~10 −2 level whereas at acidic pH it was near zero. Addition of phosphate and fluoride ions substantially enhanced the • OH aq production in the acidic pH range. It is suggested that • OH aq -radical formation in TiO 2 photocatalysis can occur by oxidation of hydroxyl ions in the water layer adsorbed on TiO 2 surfaces.

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“…The synthesis of related compounds, based on the 2,3-dihydro-1,4-phthalazinedione ring, starting from phthalic anhydride [5][6][7], 3-nitrophthalic acid [8], or phthalimide [6][7][8][9], has been reported.…”

mentioning

confidence: 99%

Synthesis and biological activity evaluation of differently substituted 1,4‐dioxo‐3,4‐dihydrophthalazine‐2(1H)‐carboxamides and ‐carbothioamides

Cardia

Distinto

Maccioni

et al. 2003

Journal of Heterocyclic Chem

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Differently substituted phthalic anhydrides can react either with semicarbazide or thiosemicarbazide to give respectively 1,4-dioxo-3,4-dihydrophthalazine-2(1H)-carboxamides or 1,4-dioxo-3,4-dihydrophthalazine-2(1H)-carbothioamides under mild conditions and generally with good yields. These compounds have been tested in order to evaluate their anti-microbial activity. Furthermore a new synthetic pathway to phthalazino[2,3-b]phthalazine-5,7,12,14-tetraone has been devised

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5. Chemiluminescent organic compounds. Part II. The effect of substituents on the closure of phthalhydrazides to 5- and 6-membered rings

Cited by 39 publications

References 0 publications

The Metabolism of Thalidomide: The Fate of Thalidomide and Some of Its Hydrolysis Products in Various Species

The Metabolism of Thalidomide: The Fate of Thalidomide and Some of Its Hydrolysis Products in Various Species

Generation of Free OHaq Radicals by Black Light Illumination of Degussa (Evonik) P25 TiO2 Aqueous Suspensions

Synthesis and biological activity evaluation of differently substituted 1,4‐dioxo‐3,4‐dihydrophthalazine‐2(1H)‐carboxamides and ‐carbothioamides

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