548475-62-3

Usage

Chemical compound

2H-Cyclohepta[4,5]furo[2,3-d]pyrimidine-2,4(3H)-dione, 1,7-dihydro-1,3-dimethyl-7-(phenylthio)(9CI)

Heterocyclic compound

Contains a unique seven-membered ring structure with nitrogen, oxygen, and sulfur atoms

Alias

Penciclovir

Function

Antiviral medication used to treat herpes simplex infections

Mechanism of action

Inhibits replication of viral DNA to prevent spread and growth of herpes virus

Indication

Treats cold sores caused by herpes simplex virus

Activity

Potent and selective inhibitor of viral DNA polymerase

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 3839-48-3 2-chlorotropone 
• 108-98-5 thiophenol 
• 548475-44-1 1,3-dimethyl-5-(1'-oxocycloheptatrien-2'-yl)-pyrimidine-2(1H),4(3H),6(5H)-trione 
• 548475-60-1 5-(2'-diethylaminocyclohepta-2',4',6'-trienylidene)pyrimidine-2(1H),4(3H),6(5H)-trione 
• 548475-68-9 5a,7-dihydro-7,9-dimethyl-5a-methoxycyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dione 

Relevant academic research and scientific papers

Novel synthesis and properties of 7,9-dimethylcyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dionylium tetrafluoroborate: Autorecycling oxidation of some alcohols under photo-irradiation

Three-step reactions starting from 2-chlorotropone with barbituric acid afforded novel 7,9-dimethylcyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dionylium tetrafluoroborate (9·BF4-), which is the isoelectronic compound of the 5-ethyl-3-methyllumiflavinium ion. The stability of cation 9 is expressed by the pKR+ value, which was determined spectrophotometrically, as ca. 6.0. The electrochemical reduction of 9 exhibited low reduction potential at -0.58 (V vs Ag/AgNO3), upon cyclic voltammetry (CV). In a search for the reactivity, reactions of 9·BF4- with some nucleophiles, hydroxide, hydride, amines, thiols, and methanol, were carried out to exhibit that the introduction of nucleophiles is dependent on the nucleophile itself. The photo-induced oxidation reactions of some alcohols catalyzed by 9·BF4- under aerobic conditions were carried out to give the corresponding carbonyl compounds in more than 100% yield [based on compound 9·BF4-], suggesting the oxidizing function of 9·BF4- toward alcohols in the autorecycling process. The UV-vis and fluorescence spectra of 9 were studied to suggest the electron transfer from alcohols to the excited 9.