Synthesis of 4‐fluoro‐2, 3‐dimethyl‐1‐phenyl‐3‐pyrazoline‐5‐one (4‐fluoroantipyrine) and <sup>18</sup>f‐labeled analog by direct fluorination of antipyrine with molecular fluorine

Shiue, Chyng‐Yann; Wolf, Alfred P.

doi:10.1002/jlcr.2580180718

Cited by 17 publications

(2 citation statements)

References 14 publications

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“…4-Isopropyl-3-methyl-l-phenylpyrazol-5-one (2). A mixture of compound 3 and acetone dissolved in methanol was hydrogenated over Raney nickel as described by Volk.14 The resulting product 2 was recrystallized from methanol-water: mp 117-118 °C (lit.14 mp 114-117 °C); NMR 1.13 (6 H, t, -CH(CH3)2), 2.18 (3 H, s, -CH3), 2.5 (1 H, m, -CR(CH3)2), 3.1 (1 H, s, NH), [7][8] ppm (5 H, m, phenyl).…”

Section: Methodsmentioning

confidence: 99%

Carbon-11-labeled 4-isopropylantipyrine: preparation and biological evaluation as a blood flow tracer in positron emission tomography (PET)

Stone‐Elander¹,

Ingvar²,

Johnström³

et al. 1985

J. Med. Chem.

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Radiolabeled 4-isopropylantipyrine (1) has been synthesized and evaluated as a tracer for the measurement of cerebral blood flow (CBF). Methylation of 4-isopropyl-3-methyl-1-phenylpyrazol-5-one (2) with [14C]methyl iodide in acetonitrile gave [14C]-1 in radiochemical yields of 10-20%. Its blood-brain partition coefficient in rats was determined to be 0.62 +/- 0.03 (mean +/- SE). Autoradiographic determination of regional cerebral blood flow under normal flow conditions indicated that [14 C]-1 gives results essentially identical with those obtained with the widely used tracer [14C]-4-iodoantipyrine ( [14C]-IAP). Studies performed in high-flow states indicated that [14C]-1 is not more diffusion limited than [14C]-IAP. A rapid synthesis was therefore developed for the preparation of [11C]-1. Radiochemical yields were increased to 40-50% when the alkylation of 2 with [11C]methyl iodide was performed in dimethyl sulfoxide using solid potassium hydroxide as a base. Since the 11C-labeled compound can easily be produced in large quantities and since the tracer is not diffusion limited at flow rates commonly observed in normal and most pathological states in man, [11C]-4-isopropylantipyrine will be used for in vivo studies of CBF using positron emission tomography.

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Section: Methodsmentioning

confidence: 99%

Carbon-11-labeled 4-isopropylantipyrine: preparation and biological evaluation as a blood flow tracer in positron emission tomography (PET)

Stone‐Elander¹,

Ingvar²,

Johnström³

et al. 1985

J. Med. Chem.

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“…Reliable Jt,s can be determined from data obtained in single-time experiments. 29 Thirty to fifty microcuries of [ 32 was constantly infused intravenously for 1 minute. Twenty-microliter arterial blood samples were drawn at 5-second intervals after the start of the infusion of [ I8 F]FAP.…”

Section: Methodsmentioning

confidence: 99%

Tolerance of the cerebral venous system to retrograde perfusion pressure in focal cerebral ischemia in rats.

Ueda

Yamamoto

Takara

et al. 1989

Stroke

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Using quantitative doable-tracer antoradiography, we examined the tolerance of the rat cerebral venous system hi focal cerebral ischemia to retrograde perfusion pressure into the inferior cerebral vein. At perfusion pressures of <150 mm Hg, there was no significant change hi local cerebral blood flow (LCBF) and blood-brain barrier (BBB) permeability. At pressures of >170 mm Hg, significant changes occurred in BBB permeability in the superficial cortical layers and there was a mild reduction of LCBF. In the group of rats subjected to 200 mm Hg perfusion pressure, the change hi BBB permeability extended to the entire cortical zone and significant reduction of LCBF occurred. Our results indicate for the first time that during conditions of focal cerebral ischemia, the rat cerebral venous system can tolerate up to 150 mm Hg of retrograde perfusion pressure into the cerebral venous system without any change in BBB permeability or hi LCBF. However, progressive change hi BBB permeability and reduction in LCBF occur once the perfusion pressure exceeds 170 mm Hg. This finding may permit more efficient delivery of cytoprotective agents into ischemic tissue. (Stroke 1989; 20:378-385)

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The Formation of the C  F Bond: The Last Twelve Years

Rozen

2009

Patai's Chemistry of Functional Groups

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Introduction Nucleophilic Fluorinating Reagents Electrophilic Fluorinating Reagents Synthesis of Compounds Containing The 18 F Isotope For Use In Positron‐Emitting Tomography Recent Reviews on Selective Fluorination Methods

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Synthesis of 4‐fluoro‐2, 3‐dimethyl‐1‐phenyl‐3‐pyrazoline‐5‐one (4‐fluoroantipyrine) and ¹⁸f‐labeled analog by direct fluorination of antipyrine with molecular fluorine

Cited by 17 publications

References 14 publications

Carbon-11-labeled 4-isopropylantipyrine: preparation and biological evaluation as a blood flow tracer in positron emission tomography (PET)

Carbon-11-labeled 4-isopropylantipyrine: preparation and biological evaluation as a blood flow tracer in positron emission tomography (PET)

Tolerance of the cerebral venous system to retrograde perfusion pressure in focal cerebral ischemia in rats.

The Formation of the C  F Bond: The Last Twelve Years

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Synthesis of 4‐fluoro‐2, 3‐dimethyl‐1‐phenyl‐3‐pyrazoline‐5‐one (4‐fluoroantipyrine) and 18f‐labeled analog by direct fluorination of antipyrine with molecular fluorine

Cited by 17 publications

References 14 publications

Carbon-11-labeled 4-isopropylantipyrine: preparation and biological evaluation as a blood flow tracer in positron emission tomography (PET)

Carbon-11-labeled 4-isopropylantipyrine: preparation and biological evaluation as a blood flow tracer in positron emission tomography (PET)

Tolerance of the cerebral venous system to retrograde perfusion pressure in focal cerebral ischemia in rats.

The Formation of the C  F Bond: The Last Twelve Years

Contact Info

Product

Resources

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Synthesis of 4‐fluoro‐2, 3‐dimethyl‐1‐phenyl‐3‐pyrazoline‐5‐one (4‐fluoroantipyrine) and ¹⁸f‐labeled analog by direct fluorination of antipyrine with molecular fluorine