The specific inhibition of vesicular stomatitis virus replication by toyocamycin

Moyer, Sue A.; Holmes, K. Susan

doi:10.1016/0042-6822(79)90528-2

Cited by 7 publications

(4 citation statements)

References 24 publications

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“…4-Amino-7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine-5-carboxamidoxime (9). Compound 6 (0.1 g, 0.43 mmol) was dissolved in EtOH (10 mL) containing hydroxylamine (0.15 g; 50% aqueous hydroxylamine).…”

Section: Biological Results and Discussionmentioning

confidence: 99%

“…(MeOH) 278 (15770); (pH 11) 217 (26100), 278 (13880); NMR (DMSO-d6) 3.50 (m, 4, CH2), 3.75 (s, 3, OCH3), 5.58 (s, 2, CVCH2), 7.25 (br s, 1, NH2), 7.75 (s, 1, C6-H), 8.06 (s, 1, C2-H), 8.20 (br s, 1, C=NH), 9.98 (br s, 1, NH2). Anal.…”

Section: Biological Results and Discussionmentioning

confidence: 99%

“…Hydrazine hydrate (85%) (2.0 mL) was added to a solution of compound 10 (0.52 g, 2 mmol) in absolute EtOH (10 mL). This mixture was heated at reflux temperature for 3 h and then allowed to stand at 5 °C for an NMR (DMS0-d6) 3.50 (m, 4, CH2), 4.50 (br s, 2, NH2), 4.65 (t, 1, D20 enchangeable, OH), 5.60 (s, 2, C'rCH2), 7.98 (br s, 2, C4-NH2), 8.00 (s, 1 ), 8.15 (s, 1 H), 9.75 (br s, 1, CONH); MS m/e 266. Anal.…”

Section: Biological Results and Discussionmentioning

confidence: 99%

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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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Section: Biological Results and Discussionmentioning

confidence: 99%

Section: Biological Results and Discussionmentioning

confidence: 99%

Section: Biological Results and Discussionmentioning

confidence: 99%

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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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“…These include analogues of ATP such as ara-ATP (Chanda & Banerjee, 1980) and toyocamycin (Moyer & Holmes, 1979), the pyrophosphate analogue phosphonoformate (Chanda & Banerjee, 1980), the trypsin inhibitor N-ct-tosyl-L-lysylchloromethyl ketone (Witt & Summers, 1980), the amino acid analogue cycloleucine (Moyer, 1981) and also highly basic proteins such as protamine (Banerjee et al, 1981). Although the 0022-1317/83/0000-5458 $02.00 © 1983 SGM * VSV (Indiana serotype) intracellular nucleocapsids were prepared for the replication system from baby hamster kidney cells (BHK-21/13) at 6 h post-infection as described earlier (Davis & Wertz, 1982).…”

mentioning

confidence: 99%

Inhibition of Vesicular Stomatitis Virus RNA Synthesis by 2',3'-Dideoxycytidine 5'-Triphosphate

Patton

Davis

Wertz

1983

Journal of General Virology

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SUMMARYThe ability of the compound 2',3'-dideoxycytidine 5'-triphosphate (ddCTP) to serve as an inhibitor of viral RNA synthesis was examined using an in vitro system that supports vesicular stomatitis virus (VSV) protein synthesis, transcription and replication. Viral RNA synthesis was inhibited by 87 and 98 % of control, respectively, in reactions containing 1 mM-and 10 mM-ddCTP in place of CTP. VSV RNA replication and transcription were inhibited equally by ddCTP. At a concentration of 1 mM-ddCTP, there was no inhibitory effect on viral protein synthesis; at 10 mMddCTP, total protein synthesis was inhibited by 30% as compared to control reactions. The presence of ddCTP had no effect on the size or relative molar amounts of each protein synthesized as analysed by electrophoresis on polyacrylamide gels. This is the first report describing a compound that will inhibit VSV RNA synthesis in vitro without compromising the concurrent synthesis and modification of proteins.

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The effects of adenosine and guanosine on the replication of sindbis and vesicular stomatitis viruses in aedes albopictus cells

Stollar

Malinoski

1981

Virology

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The specific inhibition of vesicular stomatitis virus replication by toyocamycin

Cited by 7 publications

References 24 publications

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

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

Inhibition of Vesicular Stomatitis Virus RNA Synthesis by 2',3'-Dideoxycytidine 5'-Triphosphate

The effects of adenosine and guanosine on the replication of sindbis and vesicular stomatitis viruses in aedes albopictus cells

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