Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine)

The synthesis of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine, 2) has been accomplished from 3-(ethoxycarbonyl)pyrrole-2-acetonitrile. In contrast to 3-deazaguanine, compound 2 did not show any antitumor, antiviral, or antibacterial properties. Furthermore, it was not a substrate f...

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Veröffentlicht in:	Journal of medicinal chemistry 1984-12, Vol.27 (12), p.1737-1739
Hauptverfasser:	Schneller, Stewart W, Luo, Jiann Kuan, Hosmane, Ramachandra S, De Clercq, Erik, Stoeckler, Johanna D, Agarwal, Kailash C, Parks, Robert E, Saunders, Priscilla P
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Anti-Bacterial Agents Anti-Infective Agents - chemical synthesis Cell Division - drug effects Cell Line Chemistry Cricetinae Cricetulus Erythrocytes - enzymology Escherichia coli - drug effects Exact sciences and technology Female Guanine - analogs & derivatives Guanine - chemical synthesis Guanine - pharmacology Guanine - toxicity Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Humans Hypoxanthine Phosphoribosyltransferase - blood Indicators and Reagents Microbial Sensitivity Tests Organic chemistry Ovary Preparations and properties Purine-Nucleoside Phosphorylase - blood Structure-Activity Relationship Viruses - drug effects
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Zusammenfassung:	The synthesis of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine, 2) has been accomplished from 3-(ethoxycarbonyl)pyrrole-2-acetonitrile. In contrast to 3-deazaguanine, compound 2 did not show any antitumor, antiviral, or antibacterial properties. Furthermore, it was not a substrate for hypoxanthine-guanine phosphoribosyltransferase or purine nucleoside phosphorylase.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00378a037