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2(5)-Substituted 4-hydroxy-3,4-diphenylcyclopent-2-en-1-ones easily react with 2.5 molar excess of maleic anhydride to give 1(4)-substituted 7,8-diphenylbicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydrides containing alkyl groups at bridgehead of the bicycle. The stereochemistry of the obtained bicyclic bis-anhydrides was determined to be syn-syn . [ABSTRACT FROM AUTHOR]

Rigid amphipathic fusion inhibitors (RAFIs) are potent antivirals based on a perylene core linked with a nucleoside moiety. Sugar-free analogues of RAFIs, 5-(perylen-3-ylethynyl)uracil-1-acetic acid 1 and its amides 2 , were synthesized using combined protection group strategy. Compounds 1 and 2 appeared to have low toxicity on porcine embryo kidney (PEK) or rhabdomiosarcoma (RD) cells together with remarkable activity against enveloped tick-borne encephalitis virus (TBEV): EC 50 values vary from 0.077 μM to subnanomolar range. Surprisingly, 3-pivaloyloxymethyl (Pom) protected precursors 7 and 8 showed even more pronounced activity. All the compounds showed no activity against several non-enveloped enteroviruses, except 4-hydroxybutylamides 2d , g , which inhibited the reproduction of enterovirus A71 with EC 50 50–100 μM, with a non-specific mode of action. The results suggest that the carbohydrate moiety of RAFI nucleosides does not play a crucial role in their antiviral action, and biological activity of the 5-(perylen-3-ylethynyl)uracil scaffold can be effectively modulated by substituents in positions 1 and 3. The high antiviral activity of these new compounds, coupled with low toxicity advocate their potential role in antiviral therapy. Image 1 • 5-(Perylen-3-ylethynyl)uracil-1-acetic acid derivatives were synthesized using combined protection group strategy. • Four compounds tested showed activity against tick-borne encephalitis virus (TBEV) in subnanomolar range. • One compound inhibited reproduction of Enterovirus A with a non-specific mode of action. • 5-(Perylen-3-ylethynyl)uracil is an antiviral scaffold, and substituents in positions 1 and 3 modulate the activity. [ABSTRACT FROM AUTHOR]

The well-known and rapidly growing phenomenon of bacterial resistance to antibiotics is caused by uncontrolled, excessive and inappropriate use of antibiotics. One of alternatives to antibiotics is Photodynamic Antibacterial Chemotherapy (PACT). In the present study, the effect of PACT using a photosensitizer Rose Bengal alone and in combination with antibiotics including methicillin and derivatives of sulfanilamide synthesized by us was tested against antibiotic-sensitive and antibiotic-resistant clinical isolates of Gram-positive S. aureus and Gram-negative P. aeruginosa. Antibiotic-sensitive and resistant strains of P. aeruginosa were eradicated by Rose Bengal under illumination and by sulfanilamide but were not inhibited by new sulfanilamide derivatives. No increase in sensitivity of P. aeruginosa cells to sulfanilamide was observed upon a combination of Rose Bengal and sulfanilamide under illumination. All tested S. aureus strains (MSSA and MRSA) were effectively inhibited by PACT. When treated with sub-MIC concentrations of Rose Bengal under illumination, the minimum inhibitory concentrations (MIC) of methicillin decreased significantly for MSSA and MRSA strains. In some cases, antibiotic sensitivity of resistant strains can be restored by combining antibiotics with PACT. [ABSTRACT FROM AUTHOR]

The article talks about the synthesis of 5-(Perylen-3-ylethynyl)-arabino-uridine (aUY11, 1), an antiviral. discussing the Sonogashira coupling of 5-iodo nucleoside derivative with 3-ethynylperylene in synthesis of (aUY11, 1); and the solvent properties of peryleneethynyl nucleoside 1.

Two novel analogues of the highly fluorescent and potent antiviral compound, 5-(perylen-3-ylethynyl)-2′-deoxyuridine, containing elongated rigid linkers, butadiyne and 1,4-diethynylphenylene, were synthesized from the corresponding trimethylsilyl alkynes using a one-pot desilylation/Sonogashira reaction as the key step. Their spectral properties are compared to those of the parent perylenylethynyl nucleoside. [ABSTRACT FROM AUTHOR]

3-Ethynylperylene 1 , an important precursor for fluorescent dyes, fluorescent nucleosides, and potent nucleoside-based antivirals, has been prepared from perylene on a multigram scale (3 steps, 55% overall yield). A simple synthesis of 2-ethynylperylene 2 from perylene (5 steps, 20% yield) has been developed. UV and fluorescence spectra of the ethynylperylenes 1 and 2 are compared to those of perylene. [ABSTRACT FROM AUTHOR]