The formation and metabolism of N-hydroxymethyl compounds. Part 6. The synthesis of S-amidomethyl-, S-ureidomethyl-, and S-(1,3,5-triazin-2-ylaminomethyl)-glutathione derivatives

Treatment of 2‐chloro‐4,6‐(dimethylamino)‐1,3,5‐triazine with trideuteromethylamine gave 4,6‐(dimethylamino)‐2‐trideuteromethyl‐1,3,5‐triazine, an isotopomer of the experimental anticancer agent pentamethylmelamine (PMM). Mitsunobu coupling with 1,2‐dimethyl‐3‐hydroxymethyl‐5‐methoxy‐indole‐4,7‐dione gave 1,2‐dimethyl‐3‐(N‐(4,6‐bis(dimethylamino)‐1,3,5‐triazin‐2‐yl)‐N‐trideuteromethylaminomethyl)‐5‐methoxyindole‐4,7‐dione. This conjugate is a potential reductively triggered prodrug of PMM. Copyright © 2002 John Wiley & Sons, Ltd.

show abstract

The generation of potentially toxic, reactive iminium ions from the oxidative metabolism of xenobiotic N-alkyl compounds

Overton¹,

Hickman²,

Threadgill³

et al. 1985

Biochemical Pharmacology

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

The formation and metabolism of N-hydroxymethyl compounds. Part 6. The synthesis of S-amidomethyl-, S-ureidomethyl-, and S-(1,3,5-triazin-2-ylaminomethyl)-glutathione derivatives

Abstract: Durch Reaktion der N‐Hydroxymethyl‐ und N‐Alkoxymethylverbindungen (III), (VI), (VII) sowie des Produkts aus dem Triazin (X) und Formaldehyd (XI) mit Glutathion (IV) bzw. N‐Acetylcystein (VIII) entstehen I66 Titelverbindungen des Typs (V), (IX) oder (XII).

Cited by 8 publications

References 3 publications

ChemInform Abstract: THE FORMATION AND METABOLISM OF N‐HYDROXYMETHYL COMPOUNDS. PART 6. THE SYNTHESIS OF S‐AMIDOMETHYL‐, S‐UREIDOMETHYL‐, AND S‐(1,3,5‐TRIAZIN‐2‐YLAMINOMETHYL)GLUTATHIONE DERIVATIVES

ChemInform Abstract: THE FORMATION AND METABOLISM OF N‐HYDROXYMETHYL COMPOUNDS. PART 6. THE SYNTHESIS OF S‐AMIDOMETHYL‐, S‐UREIDOMETHYL‐, AND S‐(1,3,5‐TRIAZIN‐2‐YLAMINOMETHYL)GLUTATHIONE DERIVATIVES

Labelled compounds of interest as antitumour agents – VIII. Synthesis of ²H‐isotopomers of pentamethylmelamine and of a potential prodrug thereof

The generation of potentially toxic, reactive iminium ions from the oxidative metabolism of xenobiotic N-alkyl compounds

Contact Info

Product

Resources

About

The formation and metabolism of N-hydroxymethyl compounds. Part 6. The synthesis of S-amidomethyl-, S-ureidomethyl-, and S-(1,3,5-triazin-2-ylaminomethyl)-glutathione derivatives

Abstract: Durch Reaktion der N‐Hydroxymethyl‐ und N‐Alkoxymethylverbindungen (III), (VI), (VII) sowie des Produkts aus dem Triazin (X) und Formaldehyd (XI) mit Glutathion (IV) bzw. N‐Acetylcystein (VIII) entstehen I66 Titelverbindungen des Typs (V), (IX) oder (XII).

Cited by 8 publications

References 3 publications

ChemInform Abstract: THE FORMATION AND METABOLISM OF N‐HYDROXYMETHYL COMPOUNDS. PART 6. THE SYNTHESIS OF S‐AMIDOMETHYL‐, S‐UREIDOMETHYL‐, AND S‐(1,3,5‐TRIAZIN‐2‐YLAMINOMETHYL)GLUTATHIONE DERIVATIVES

ChemInform Abstract: THE FORMATION AND METABOLISM OF N‐HYDROXYMETHYL COMPOUNDS. PART 6. THE SYNTHESIS OF S‐AMIDOMETHYL‐, S‐UREIDOMETHYL‐, AND S‐(1,3,5‐TRIAZIN‐2‐YLAMINOMETHYL)GLUTATHIONE DERIVATIVES

Labelled compounds of interest as antitumour agents – VIII. Synthesis of 2H‐isotopomers of pentamethylmelamine and of a potential prodrug thereof

The generation of potentially toxic, reactive iminium ions from the oxidative metabolism of xenobiotic N-alkyl compounds

Contact Info

Product

Resources

About

Labelled compounds of interest as antitumour agents – VIII. Synthesis of ²H‐isotopomers of pentamethylmelamine and of a potential prodrug thereof