Effect of toyocamycin on the synthesis of the 70S RNA of a murine retrovirus

Larsen, Christian‐Jacques; Mauchauffé, M; Hamelin, Richard; Peraudeau, L; Fedele, L A; Tavitian, Armand

doi:10.1093/nar/6.4.1547

Cited by 5 publications

(1 citation statement)

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“…Methyl 4-Amino-7-[(2-hydroxyethoxy)methyl]pyrrolo-[2,3-d ]pyrimidine-5-formimidate (10). Compound 6 (0.5 g, 2.15 mmol) was dissolved in dry MeOH (15 mL).…”

Section: Biological Results and Discussionmentioning

confidence: 99%

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

Gupta

Nassiri²,

Coleman³

et al. 1989

J. Med. Chem.

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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 6 and 8-12 were tested for cytotoxicity to L1210 murine leukemic cells in vitro. None of these compounds caused significant inhibition of cell growth. Evaluation of compounds 4 and 6-12 for activity against human cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1) revealed that only the thioamide (11) was active. It inhibited HCMV but not HSV-1 at concentrations producing only slight cytotoxicity in human foreskin fibroblasts (HFF cells) and KB cells.

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“…Methyl 4-Amino-7-[(2-hydroxyethoxy)methyl]pyrrolo-[2,3-d ]pyrimidine-5-formimidate (10). Compound 6 (0.5 g, 2.15 mmol) was dissolved in dry MeOH (15 mL).…”

Section: Biological Results and Discussionmentioning

confidence: 99%