Antiviral activity of some .beta.-diketones. 2. Aryloxy alkyl diketones. In vitro activity against both RNA and DNA viruses

Diana, Guy D.; Salvador, U. Joseph; Zalay, Ethel S.; Carabateas, Philip M.; Williams, Gordon L.; Collins, Joseph C.; Pancic, F.

doi:10.1021/jm00216a004

Cited by 46 publications

(10 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[51][52][53][54] Several modifications to improve activity led to the development of arildone (WIN38020), an aryl diketone. This compound was shown to selectively inhibit poliovirus replication in vitro by preventing virion uncoating.…”

Section: B Win Compoundsmentioning

confidence: 99%

Selective inhibitors of picornavirus replication

Palma

Vliegen

Clercq

et al. 2008

Medicinal Research Reviews

232

217

View full text Add to dashboard Cite

Picornaviruses cover a large family of pathogens that have a major impact on human but also on veterinary health. Although most infections in man subside mildly or asymptomatically, picornaviruses can also be responsible for severe, potentially life-threatening disease. To date, no therapy has been approved for the treatment of picornavirus infections. However, efforts to develop an antiviral that is effective in treating picornavirus-associated diseases are ongoing. In 2007, Schering-Plough, under license of ViroPharma, completed a phase II clinical trial with Pleconaril, a drug that was originally rejected by the FDA after a New Drug Application in 2001. Rupintrivir, a rhinovirus protease inhibitor developed at Pfizer, reached clinical trials but was recently halted from further development. Finally, Biota's HRV drug BTA-798 is scheduled for phase II trials in 2008. Several key steps in the picornaviral replication cycle, involving structural as well as non-structural proteins, have been identified as valuable targets for inhibition. The current review aims to highlight the most important developments during the past decades in the search for antivirals against picornaviruses.

show abstract

Section: B Win Compoundsmentioning

confidence: 99%

Selective inhibitors of picornavirus replication

Palma

Vliegen

Clercq

et al. 2008

Medicinal Research Reviews

232

217

View full text Add to dashboard Cite

show abstract

“…The search for effective antirhinovirus agents has yielded a wealth of compounds belonging to widely varying chemical classes: thiosemicarbazones (20), isoquinolines (35,43), triazinoindoles (27), guanidines (5), benzoates (30), furanyls (2), benzimidazoles (12), thiourea (18), diketones (14,16,17), flavans (3,32), flavones (25), chalcones (24), nitrobenzenes (34,41), and isoxazoles (15,31). The most recently developed antirhinovirus compounds (3,15,24,31) reach their MICs within the range of 0.001 to 0.01 ,ug/ml.…”

mentioning

confidence: 99%

Antirhinovirus activity of purine nucleoside analogs

Clercq¹,

Bernaerts²,

Bergstrom³

et al. 1986

Antimicrob Agents Chemother

View full text Add to dashboard Cite

A wide variety of purine nucleoside (mainly tubercidin and adenosine) analogs, which had previously been shown to inhibit the replication of a broad spectrum of RNA viruses, were evaluated for their antirhinovirus activity in human diploid (WI-38) fibroblasts. Tubercidin, 5-(l-hydroxyethyl)tubercidin, 5-(2-buten-lyl)tubercidin, toyocamycin, and sangivamycin emerged as the most potent inhibitors. These compounds inhibited the replication of rhinovirus types 1A, 1B, and 9 at an MIC well below 1 ,ug/ml. However, these compounds proved cytotoxic for the uninfected host cells at concentrations which were only slightly higher (3-to 10-fold, on the average) than those required for inhibition of rhinovirus replication. The most selective inhibitor of rhinovirus replication was 3-deazaguanine, with a selectivity index of 50. None of the carbocyclic and acyclic analogs of adenosine tested exhibited a potent or selective antirhinovirus activity.The search for effective antirhinovirus agents has yielded a wealth of compounds belonging to widely varying chemical classes: thiosemicarbazones

show abstract

“…For step two we used the methodology developed in our laboratory for selective N-3-alkylation of TSAO derivatives . Finally, when the alkylation of 1 was carried out using lithium hydride in DMF (Diana et al, 1977) (method B), the yield of the C-alkylated compound 4 increased up to 40% whereas the yield of the O-alkylated compound (3) clearly diminished (6%). 3), we performed the alkylation of pentane-2,4-dione (1) with dibromohexane in the presence of potassium carbonate.…”

Section: Chemistrymentioning

confidence: 99%

An Approach towards the Synthesis of Potential Metal-Chelating TSAO-T Derivatives as Bidentate Inhibitors of Human Immunodeficiency virus Type 1 Reverse Transcriptase

Chamorro

Camarasa

Pérez-Pérez

et al. 1998

Antivir Chem Chemother

View full text Add to dashboard Cite

Novel derivatives of the potent human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) inhibitor TSAO-T have been designed, synthesized and tested for their in vitro antiretroviral activity against HIV. These TSAO-T derivatives have been designed as potential bidentate inhibitors of HIV-1 RT, which combine in their structure the functionality of a non-nucleoside RT inhibitor (TSAO-T) and a bivalent ion-chelating moiety (a β β-diketone moiety) linked through an appropriate spacer to the N-3 of thymine of TSAO-T. Some of the new compounds have an anti-HIV-1 activity comparable to that of the parent com-pound TSAO-T, but display a markedly increased antiviral selectivity. There was a clear relationship between antiviral activity and the length of the spacer group that links the TSAO molecule with the chelating moiety. A shorter spacer invariably resulted in increased antiviral potency. None of the TSAO-T derivatives were endowed with anti-HIV-2 activity.

show abstract

Antiviral activity of some .beta.-diketones. 2. Aryloxy alkyl diketones. In vitro activity against both RNA and DNA viruses

Cited by 46 publications

References 1 publication

Selective inhibitors of picornavirus replication

Selective inhibitors of picornavirus replication

Antirhinovirus activity of purine nucleoside analogs

An Approach towards the Synthesis of Potential Metal-Chelating TSAO-T Derivatives as Bidentate Inhibitors of Human Immunodeficiency virus Type 1 Reverse Transcriptase

Contact Info

Product

Resources

About