Synthesis of 14C‐labelled nitrosamines. IV synthesis of 14C‐methyl‐(1‐acetoxy) methyl nitrosamine and 1‐14C‐ethyl (acetoxy)ethyl nitrosamine

linine (Schiff-Basen) addieren Nitrosylchlorid unter Bildung von N-Alkyl-1-chlor-N-nitrosoalkylaminen 13. Durch nucleophile Substitution mit Acetat oder p-Nitrobenzoat sind daraus die Acetate 7 und 9 sowie dlep-Nitrobenzoate 8 und 10 zuganglich. Die spektroskopischen Daten und die chemischen Eigenschaften der neu dargestellten Verbindungen werden diskutiert. The Chemistry of Nitrosamines, IV. 1) -Syntheses of a-C-Functionalized N-Nilrosodialkylamines: Esters and Ethers of I-[(Alkyl)(nitroso)amino]alcohols[mines (Schiff's bases) and nitrosyl chloride react to give N-alkyl-1-chloro-N-nitrosoalkylamines 13. Nucleophilic substitution by acetate or p-nitrobenzoate affords the acetates 7 and 9 and p-nitrobenzoates 8 and I#, respectively. The spectroscopic and chemical data of the newly synthesized compounds are discussed.Bereirs 1954 konnten Barnes und Mageez) die carcinogene Wirkung von N-Nitrosodimethylamin nachweisen. Spater konnten Druckrey und Mitarb. )) zeigen, daO diese Fahigkeit, bei Applikation an Ratten Tumore hervorzurufen, nicht auf N-Nitrosodimethylamin beschrankt ist, sondern daR eine Vielzahl von N-Nitrosoverbindungen diese Eigenschaft besitzen. Sie konnten fest-,tellen, daO die carcinogene Wirkung bei N-Nitrosodialkylaminen an das Vorhandensein eines a-standigen Wasserstoffatoms gebunden ist. Es wurdc auch deutlich, da13 dies zwar eine notwendige aber keine hinreichende Bedingung ist. So sind 1 und 3 noch deutlich carcinogen, 2 und 4 dagegen i i i c l i i mehi. I H 17'Diese Befunde und eine Fulle von biochemischen Un~ersuchungen~), die den Nachweis erbrachten, daO N-Nitrosodialkylamine 5 zur Entfaltung ihrer carcinogenen Eigenschaften der metabolischen Aktivierung durch Oxygenasen bedurfen 5 ) , lassen sich zu einem Metabolisierungsschema zusammenfassen (Schema 1). Der erste Schritt besteht in der enzymkatalysierten Einfuhrung einer OH-Gruppe in Nachbarschaft zur N-Nitroso-Gruppe unter Bildung a-hydroxylierter Nitrosamine 6. Diese Verbindungen, die seit kurzem synthetisch zuglnglich sind6), gehen unter Abspaltung von C) Verlag Chernie GrnbH, D

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Chemie der Nitrosamine, IV. Synthesen von α‐C‐funktionellen N‐Nitrosodialkylaminen: Ester und Ether von 1‐[(Alkyl)(nitroso)amino]alkoholen

Müller

Kettler

Wießler

1984

Liebigs Ann. Chem.

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Embryotoxicity induced by alkylating agents: left-sided preponderance of paw malformations induced by acetoxymethyl-methylnitrosamine in mice

et al. 1985

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The alkylating agent acetoxymethyl-methylnitrosamine (DMN-OAc) triggers preferential left-sided paw defects in mice following IP administration on either day 11 or 12 of pregnancy. Predominantly, ectrodactyly and hypoplasia of the left paws were found. In an organ culture system, using limb buds of 11-day-old mouse embryos, differentiation is severely impaired following addition of 2 microM DMN-OAc to the culture medium. Left and right limbs are equally affected. In contrast, when DMN-OAc is administered in vivo to the dams with subsequent culturing of the limb buds, growth and differentiation of the left limb buds is more affected when compared to the right. Furthermore, DNA alkylation experiments were performed: in vitro, following addition of (14C)-DMN-OAc (2.3 microM) to the culture medium, the DNA alkylation rate of the limb bud DNA is determined. In vivo, following IP administration of 10 mg/kg DMN-OAc to the dams on day 11 of pregnancy, the extent of DNA alkylation of whole-embryo DNA is similar. However, the DNA alkylation rate of separately pooled left and right limb buds exhibits a two-fold difference according to the different teratogenic susceptibility. The results obtained with both in vivo and in vitro systems are consistent with the thesis that a certain amount of DNA alkylation in the tissue of the embryos is the initial step of alkylating agent-induced teratogenicity.

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Creation of a nitrosamine library labelled with 14C or tritium

Filer

2023

J Radioanal Nucl Chem

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Synthesis of ¹⁴C‐labelled nitrosamines. IV synthesis of ¹⁴C‐methyl‐(1‐acetoxy) methyl nitrosamine and 1‐¹⁴C‐ethyl (acetoxy)ethyl nitrosamine

Abstract: A scheme is developed for synthesizing 14C labelled α‐acetates of secondary α‐hydroxylated nitrosamines. In this manner 14C‐methyl (1‐acetoxy)ethyl nitrosamine and 1‐14C‐ethyl (1‐acetoxy)ethyl nitrosamine are synthesized in 16.3 and 33.3% yield, radiochemically pure.

Cited by 6 publications

References 4 publications

Chemie der Nitrosamine, IV. Synthesen von α‐C‐funktionellen N‐Nitrosodialkylaminen: Ester und Ether von 1‐[(Alkyl)(nitroso)amino]alkoholen

Chemie der Nitrosamine, IV. Synthesen von α‐C‐funktionellen N‐Nitrosodialkylaminen: Ester und Ether von 1‐[(Alkyl)(nitroso)amino]alkoholen

Embryotoxicity induced by alkylating agents: left-sided preponderance of paw malformations induced by acetoxymethyl-methylnitrosamine in mice

Creation of a nitrosamine library labelled with 14C or tritium

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