Die Reaktion von N‐(β‐Halogenäthyl)‐carbonsäureamiden mit Diäthylamin

Cassebaum, H.; Uhlig, Konrad

doi:10.1002/prac.19733150609

Cited by 6 publications

(3 citation statements)

References 10 publications

(2 reference statements)

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“…No carrier added [ 123 I]BZA 2 was synthesized using a similar procedure as described in the radiosynthesis of carrier added [ 125 I]BZA 2 . 14 A solution of 2-bromo-N-(2-(diethylamino)ethyl)benzamide 29 (1.3 mg), synthesized from 2-bromobenzoyl chloride and N,N-diethylethylenediamine using step 2 of general procedure 3, in sodium acetate buffer (200 µL of 0.16 M NaOAc in 0.7% acetic acid) was added to a dried sample of [ 123 I]INa (800 MBq) in a Wheaton conical vial and heated to 130 °C for 30 min. The reaction was cooled and mobile phase added.…”

Section: Radiolabeling Using Chloramine-t (Cat)mentioning

confidence: 99%

Synthesis and Evaluation of Novel Radioiodinated Benzamides for Malignant Melanoma

et al. 2007

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The imaging potential of a series of [123I]benzamides was studied in mice bearing B16F0 melanoma tumors. Compound [123I]25 exhibited tumor uptake >8 %ID/g at 1 h, while that of [123I]14d and [123I]25 reached a maximum of 9-12 %ID/g at 6 h. Standardized uptake values of [123I]14d were higher than 100 between 24 and 72 h after injection. In haloperidol treated animals, the tumor uptake of [123I]14d was not significantly different to controls, while significant reduction of [123I]25 uptake was observed, supporting that [123I]14d uptake relates to melanin interaction, whereas part of the mechanism of [123I]25 uptake is related to its sigma 1-receptor affinity. Benzamides 14d and 25, which display rapid and high tumor uptake, appear to be promising imaging agents for melanoma detection, while 14d, which displays a long lasting and high melanoma/nontarget ratio, is more suitable for evaluation as a potential radiotherapeutic.

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Section: Radiolabeling Using Chloramine-t (Cat)mentioning

confidence: 99%

Synthesis and Evaluation of Novel Radioiodinated Benzamides for Malignant Melanoma

et al. 2007

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“…The title nitrosamide 11 was prepared from N- (2-chloroethyl)phenylacetamide by a procedure similar to that used to prepare 10 . The pure product was obtained as pale yellow oil after chromatography in a yield of 76%.…”

Section: Methodsmentioning

confidence: 99%

“…Hydroxyethyl)phenylacetamide 13 (23), (1.79 g, 0.01 mol) was nitrosated at 0 °C according to the method of White (24) in a mixture of acetic acid (10 mL) and acetic anhydride (50 mL). Sodium nitrite (15 g, 0.22 mol) was added over a period of 5 h. Cold water (50 mL) was then added to quench the reaction.…”

Section: N-nitroso-n-(2-hydroxyethyl)phenylacetamide (10) N-(2-mentioning

confidence: 99%

A Diazonium Ion Cascade from the Nitrosation of Tolazoline, An Imidazoline-Containing Drug

Loeppky

Shi

Barnes

et al. 2008

Chem. Res. Toxicol.

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Tolazoline (1-benzylimidazoline), a representative imidazoline-containing drug, reacts readily with nitrite in acetic acid to produce a complex product mixture. Fourteen compounds have been identified as products of this transformation when an 8-fold excess of HNO2 is used. The products, which include N-nitrosoamides, esters, alcohols, and phenylacetic acid, are rationalized as arising from a cascade of reactive diazonium ions. N-Nitrosotolazoline can be isolated from the nitrosation reaction in good yield when the mixture is extracted with CH2Cl2 as the transformation progresses. It nitrosates much more rapidly (50x) than tolazoline to give, among other products, the oxime [1-( N-nitroso-2-imidazolinyl)benzylidene]hydroxylamine, which can also be produced in good yield from the reaction of tolazoline with isopropyl nitrite. At low substrate and nitrite concentrations, the main reaction products are N-nitrosotolazoline, its decomposition product N-2-hydroxyethylphenylacetamide, the above-mentioned oxime, phenyl acetic acid, and 2-hydroxyethyl phenylacetate. The tolazoline nitrosation rate in three buffer systems has been determined at pH 3.4 and 37 degrees C ( kobs = 6.25 x 10 (-5) s (-1) in 0.5 M acetate buffer with a 10 * [NO2(-)] = 250 mM). Because N-nitrosotolazoline exhibits the chemical properties of a direct-acting mutagen and carcinogen, we have used the rate data to estimate its level of formation at nitrite concentrations <3 mM. Cursory examination of the nitrosation chemistry of oxymetazoline, a related drug, is primarily focused at its electron-rich aromatic ring.

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ChemInform Abstract: REAKTION VON N‐(BETA‐HALOGENAETHYL)‐CARBONSAEUREAMIDEN MIT DIAETHYLAMIN

Cassebaum¹,

Uhlig²

1974

Chemischer Informationsdienst

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Die Reaktion von N‐(β‐Halogenäthyl)‐carbonsäureamiden mit Diäthylamin

Cited by 6 publications

References 10 publications

Synthesis and Evaluation of Novel Radioiodinated Benzamides for Malignant Melanoma

Synthesis and Evaluation of Novel Radioiodinated Benzamides for Malignant Melanoma

A Diazonium Ion Cascade from the Nitrosation of Tolazoline, An Imidazoline-Containing Drug

ChemInform Abstract: REAKTION VON N‐(BETA‐HALOGENAETHYL)‐CARBONSAEUREAMIDEN MIT DIAETHYLAMIN

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