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  • Toward the discovery of dual HCMV-VZV inhibitors: Synthesis, structure activity relationship analysis, and cytotoxicity studies of long chained 2-uracil-3-yl-N-(4-phenoxyphenyl)acetamides.

Toward the discovery of dual HCMV-VZV inhibitors: Synthesis, structure activity relationship analysis, and cytotoxicity studies of long chained 2-uracil-3-yl-N-(4-phenoxyphenyl)acetamides.

Bioorganic & medicinal chemistry (2015-10-08)
Denis A Babkov, Anastasia L Khandazhinskaya, Alexander O Chizhov, Graciela Andrei, Robert Snoeck, Katherine L Seley-Radtke, Mikhail S Novikov
ABSTRACT

The need for novel therapeutic options to fight herpesvirus infections still persists. Herein we report the design, synthesis and antiviral evaluation of a new family of non-nucleoside antivirals, derived from 1-[ω-(4-bromophenoxy)alkyl]uracil derivatives--previously reported inhibitors of human cytomegalovirus (HCMV). Introduction of the N-(4-phenoxyphenyl)acetamide side chain at N(3) increased their potency and widened activity spectrum. The most active compounds in the series exhibit submicromolar activity against different viral strains of HCMV and varicella zoster virus (VZV) replication in HEL cell cultures. Inactivity against other DNA and RNA viruses, including herpes simplex virus 1/2, points to a novel mechanism of antiviral action.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N,N-Dimethylformamide, anhydrous, 99.8%
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.9 atom % D
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2-Propanol, BioReagent, for molecular biology, ≥99.5%
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2-Propanol, ACS reagent, ≥99.5%
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2-Propanol, anhydrous, 99.5%
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N,N-Dimethylformamide, ACS reagent, ≥99.8%
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Dimethyl sulfoxide-d6, 99.9 atom % D, contains 0.03 % (v/v) TMS
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Isopropyl alcohol, ≥99.7%, FCC, FG
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N,N-Dimethylformamide, for molecular biology, ≥99%
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Isopropyl alcohol, meets USP testing specifications
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2-Propanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)
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Dimethyl sulfoxide-d6, "100%", 99.96 atom % D
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Dimethyl sulfoxide-d6, 99.5 atom % D
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2-Propanol, BioUltra, for molecular biology, ≥99.5% (GC)
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N,N-Dimethylformamide, ReagentPlus®, ≥99%
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N,N-Dimethylformamide, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.8% (GC)
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2-Propanol, puriss. p.a., ACS reagent, ≥99.8% (GC)
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2-Propanol, Laboratory Reagent, ≥99.5%
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2-Propanol, electronic grade, 99.999% trace metals basis
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2-Propanol, puriss., meets analytical specification of Ph. Eur., BP, USP, ≥99.5% (GC)
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Dimethyl sulfoxide-d6, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
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Tetramethylsilane, ACS reagent, NMR grade, ≥99.9%
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Tetramethylsilane, ≥99.0% (GC)
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Dimethyl sulfoxide-d6, 99.9 atom % D, contains 1 % (v/v) TMS
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Dimethyl sulfoxide-d6, anhydrous, 99.9 atom % D
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N,N-Dimethylformamide, biotech. grade, ≥99.9%
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Dimethyl sulfoxide-d6, "Special HOH", ≥99.9 atom % D
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Tetramethylsilane, electronic grade, ≥99.99% trace metals basis
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Dimethyl sulfoxide-d6, "100%", 99.96 atom % D
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N,N-Dimethylformamide, ACS spectrophotometric grade, ≥99.8%