Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones

Jarvest, Richard L.; Pinto, Ivan L.; Ashman, Stephen; Dabrowski, Christine; Fernandez, Annabellee V.; Jennings, L. J.; Lavery, Patrick; Tew, David G.

doi:10.1016/s0960-894x(99)00004-9

Cited by 74 publications

(15 citation statements)

References 11 publications

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“…The ultimate position of substituted 2-aminothiophenes in this field comes from their advantageous properties -the thiophene ring as is bioisosteric replacement for phenyl group broadly present in an active drugs, the thiophene core exists in many natural and synthetic pharmaceuticals and moreover, they represent an active precursors in broad range of synthetic pathways towards compounds used in therapy. 133,134 4.1.1 Synthesis of 3-deazathiamine. The synthesis of 3-deazathiamine 61 was effected in ten chemical steps, though it was necessary to prepare and isolate substituted 2-aminothiophene.…”

Section: Synthesis Of Pharmaceuticals and Drugsmentioning

confidence: 99%

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Puterová¹,

Krutošíková²,

Végh³

2010

Arkivoc

177

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Chemistry of 2-aminothiophenes is arguably one of the most extensive and dynamic field of present-day thiophene research. Since 1961 when first report on the Gewald reaction was reported it became a universal method for synthesis of substituted 2-aminothiophenes and has gained prominence in recent times. The availability of reagents and the mild reaction conditions all contribute to the versatility of this reaction. This review summarizes the synthetic strategies for substituted 2-aminothiophenes. Consequently, details about the proposed mechanism of Gewald-like reactions and the wide scope of substituted 2-aminothiophenes for real life applications.

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Section: Synthesis Of Pharmaceuticals and Drugsmentioning

confidence: 99%

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Puterová¹,

Krutošíková²,

Végh³

2010

Arkivoc

177

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“…The solid formed was collected by filtration, washed with ethanol (20 mL), dried and crystallized from absolute ethanol. (2). -A suspension of dry compound 1 (0.01 mol) and hydrazine hydrate (5 mL) and (30 mL) absolute ethanol was stirred under gentle reflux.…”

Section: Synthesesmentioning

confidence: 99%

Design and synthesis of novel thiophenecarbohydrazide, thienopyrazole and thienopyrimidine derivatives as antioxidant and antitumor agents

Abu‐Hashem¹,

Shehry²,

Badria³

2010

Acta Pharmaceutica

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The ultimate position of substituted 2-aminothiophenes in the field of drug design and synthesis of pharmaceuticals comes from their advantageous properties. The thiophene ring is bioisosteric replacement for the phenyl group broadly present in active drugs; the thiophene core exists in many natural and synthetic pharmaceuticals (1, 2). In the present work, ethyl-2-aminothiophene-3-carboxylic was expressed as a synthone for many new condensed heterocyclic systems viz. thieno [2,3-d] 2-Amino-5-acetyl-4-methyl-thiophene-3-carboxylic acid ethyl ester (1) and 5-acetyl-2-amino-4-methylthiophene--3-carbohydrazide (2) were synthesized and used as starting materials for the synthesis of new series of 1-pyrimidin-4(3H)-one (10) and 5-methyl-6-acetyl-2--thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one (12) as potential antioxidant and antitumor agents. Pharmacological tests showed that compounds 6a, 6b, 8, 10 and 12 exhibited significant antitumor and antioxidant activity.

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“…Herpesviruses encode serine proteases that do not show homology with other proteins outside the herpesvirus family [35]. Some of the more promising inhibitors belong to N-acyl analogues of 5-methylthieno [2,3-a]oxazinone [36]. HSV helicase is also a potential target for antiviral chemotherapy.…”

Section: Present Therapiesmentioning

confidence: 99%

New treatments for genital herpes

Snoeck

Clercq

2002

Current Opinion in Infectious Diseases

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Genital herpes is a sexually transmitted disease that has been widely investigated from both an epidemiological and a diagnostic viewpoint. Better knowledge of the disease has pointed to the important role of asymptomatic herpes simplex virus type 2 shedding as a major culprit for the spread of the virus in the world, the latest statistics showing that the incidence of genital herpes is constantly increasing. The reference compound for the treatment and prophylaxis of genital herpes is acyclovir. Recently, two drugs with better oral bioavailability, valaciclovir, the oral prodrug of acyclovir, and famciclovir, the oral prodrug of penciclovir, have been made available. Nevertheless, there is a need to develop additional approaches, to extend the therapeutic possibilities and to face the problem of emerging resistant viruses, mostly in immunocompromised patients. Therefore, efforts have been made in different directions including the exploration of new targets for antiviral chemotherapy, the use of immunomodulators and the development of specific vaccines.

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Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones

Cited by 74 publications

References 11 publications

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Design and synthesis of novel thiophenecarbohydrazide, thienopyrazole and thienopyrimidine derivatives as antioxidant and antitumor agents

New treatments for genital herpes

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