PMID: 2500527Jul 1, 1989Paper

Synthesis, cytotoxicity, and antiviral activity of certain 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine nucleosides related to toyocamycin and sangivamycin

Journal of Medicinal Chemistry
P K GuptaL B Townsend

Abstract

A number of 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine derivatives related to the nucleoside antibiotics toyocamycin and sangivamycin were prepared and tested for their biological activity. Treatment of the sodium salt of 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine (1) with (2-acetoxyethoxy)methyl bromide (2) afforded a mixture of 4-amino-6-bromo-5-cyano-7-[(2-acetoxyethoxy)methyl]pyrrolo[2,3-d] pyrimidine (3) and the corresponding N1 isomer. Debromination of this mixture gave the corresponding 4-amino-5-cyano-7-[(2-acetoxyethoxy)-methyl]pyrrolo[2,3-d]pyrimidi ne (4) and 4-amino-5-cyano-1-[(2-acetoxyethoxy)methyl]pyrrolo[2,3-d]pyrimidin e (5). Deacetylation of 4 and 5 furnished 4-amino-5-cyano-7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine (6) and the corresponding N1 isomer (7), respectively. The sites of attachment for the acyclic moiety for 6 and 7 were assigned on the basis of UV spectral studies as well as 13C NMR spectroscopy. Conventional functional group transformation of 6 provided a number of novel 5-substituted derivatives (8-10), including the sangivamycin derivative 8. The methyl formimidate derivative 10 was converted to the thioamide derivative 11 and the carbohydrazide derivative 12. Compounds ...Continue Reading

Citations

Jan 1, 1993·International Journal of Antimicrobial Agents·J Neyts, E De Clercq
Nov 14, 1997·Bioorganic & Medicinal Chemistry·J S MadalengoitiaT L Macdonald
Sep 2, 2006·Bioorganic Chemistry·Chamakura V N S VaraprasadZhi Hong
Oct 11, 2012·Organic & Biomolecular Chemistry·Francesca BartocciniWalter Cabri
Jul 6, 2002·The Journal of Organic Chemistry·Davood Nematollahi, Hassan Goodarzi
Jan 28, 2009·Phytochemistry·Ken-ichiro HayashiHiroshi Nozaki

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