The DOI matches its Crossref record; 10 of the 10 references it cites were found in a registry or an index.
Design, Synthesis, and Antiviral Evaluations of 1-(Substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as Nonnucleoside Analogues of 2,5,6-Trichloro-1-(β-d-ribofuranosyl)benzimidazole
Open accessAbstract
We have recently reported that certain ribosylated polyhalogenated benzimidazoles are potent and selective inhibitors of HCMV replication at noncytotoxic concentrations. To extend the structure-activity relationship beyond these first-generation compounds, we alkylated 5,6-dichloro-2-substituted-benzimidazoles with either a series of substituted benzyl halides or (2-bromoethyl)benzene to obtain five series of nonnucleoside analogues. Evaluation of these compounds for activity against herpes viruses revealed that the new compounds were less active than the benzimidazole ribonucleosides against human cytomegalovirus (HCMV) and inactive against herpes simplex virus type 1 (HSV-1). However, as part of our broader antiviral testing, we found that some of these compounds were active against HIV. Comparisons of the biological data revealed that a chloro or bromo group was required at the 2-position for the best separation of activity against HIV and cytotoxicity. Evaluation of the most active compounds against drug-resistant HIV suggested that they act by a mechanism other than inhibition of reverse transcriptase.
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Cites
HIV with Reduced Sensitivity to Zidovudine (AZT) Isolated During Prolonged Therapy
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Nunberg, J. H., Schleif, W. A., Boots, E. J., O'Brien, J. A., Quintero, J. C., Hoffman, J. M., Emini, E. A., & Goldman, M. E. (1991) · Journal of Virology · doi:10.1128/jvi.65.9.4887-4892.1991 · Cited by 363
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Townsend, L. B., Devivar, R. V., Turk, S. R., Nassiri, M. R., & Drach, J. C. (1995) · Journal of Medicinal Chemistry · doi:10.1021/jm00020a025 · Cited by 186
Self-citationThree-dimensional analysis of the synergistic cytotoxicity of ganciclovir and zidovudine
Prichard, M. N., Prichard, L. E., Baguley, W. A., Nassiri, M. R., & Shipman, C. (1991) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.35.6.1060 · Cited by 92
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Self-citationON THE ROLE OF RIBONUCLEIC ACID IN ANIMAL VIRUS SYNTHESIS
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Cited by
The therapeutic journey of benzimidazoles: A review
Bansal, Y., & Silakari, O. (2012) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2012.09.013 · Cited by 817
Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives
Refaat, H. M. (2010) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2010.03.022 · Cited by 279
Metadata
- Authors
- Porcari, A. R., Devivar, R. V., Kucera, L. S., Drach, J. C., & Townsend, L. B.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1998-03-15
- Volume
- 41
- Issue
- 8
- Pages
- 1252-1262
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1988579458
- Cited by
- 272
- References
- 10
- FWCI
- 2.12
- Type
- journal article
- Language
- en
- Open access
- green
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