18602-85-2Relevant academic research and scientific papers
Novel radiosynthesis of PET HSV-tk gene reporter probes [ 18F]FHPG and [18F]FHBG employing dual Sep-Pak SPE techniques
Wang, Ji-Quan,Zheng, Qi-Huang,Fei, Xiangshu,Mock, Bruce H.,Hutchins, Gary D.
, p. 3933 - 3938 (2003)
Positron emission tomography (PET) herpes simplex virus thymidine kinase (HSV-tk) gene reporter probes 9-[(3-[18F]fluoro-1-hydroxy-2-propoxy) methyl]guanine ([18F]FHPG) and 9-(4-[18F]fluoro-3- hydroxymethylbutyl)guanine ([18F]FHBG) were prepared by nucleophilic substitution of the appropriate tosylated precursors with [18F]KF/ Kryptofix 2.2.2 followed by a quick deprotection reaction and purification with a simplified dual Silica Sep-Pak solid-phase extraction (SPE) method in 15-30% radiochemical yield.
Chitosan–silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method
Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Piltan, Mohammad Amin
, p. 113 - 124 (2019/07/30)
Abstract: The presilylation of purine and pyrimidine nucleobases as well as other related N-heterocycles with HMDS utilizing chitosan–silica sulfate nanohybrid (CSSNH) is described. CSSNH is proved to be a useful, highly efficient and eco-friendly heterogeneous nanohybrid catalyst for silylation of nucleobases. The presilylated nucleobases then underwent the reaction with different sources of carbon electrophiles to afford the desired N-alkyl-substituted derivatives in good-to-excellent yields. CSSNH exhibits several advantageous involving ease of handling and preparation, low cost, reusability and environmental benignity. These unique properties render the CSSNH to be an ideal candidate for use in green industrial processes. Graphic abstract: [Figure not available: see fulltext.].
Silica sulfuric acid (SSA) as a highly efficient heterogeneous catalyst for persilylation of purine and pyrimidine nucleobases and other N-heterocycles using HMDS
Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Divar, Masoumeh,Behrouz, Somayeh
experimental part, p. 1943 - 1954 (2010/11/16)
Purine and pyrimidine nucleobases and other N-heterocycles have been silylated with HMDS in excellent yields in the presence of a catalytic amount of silica sulfuric acid (SSA) as a heterogeneous catalyst. SSA utilizes a shorter reaction time and higher yields of silylated nucleobases. SSA is reusable for several times without a decrease in reactivity or yield of silylated adducts. Copyright
An Improved Total Synthesis of PET HSV-tk Gene Expression Imaging Agent 9-[(3-[18F]Fluoro-1-hydroxy-2-propoxy)methyl]guanine ([ 18F]FHPG)
Wang, Ji-Quan,Zheng, Qi-Huang,Fei, Xiangshu,Liu, Xuan,Gardner, Thomas A.,Kao, Chinghai,Raikwar, Sudhanshu P.,Glick-Wilson, Barbara E.,Sullivan, Michael L.,Mock, Bruce H.,Hutchins, Gary D.
, p. 917 - 932 (2007/10/03)
An improved total synthesis of [18F]FHPG starting from 1,3-dibenzyloxy-2-propanol and guanine has been developed. [18F]FHPG was prepared by nucleophilic substitution of the appropriate precursor with [18F]KF/ Kryptofix 2.2.2 followed by a quick deprotection reaction and purification with a simplified Silica Sep-Pak solid-phase extraction (SPE) method in 10-15% radiochemical yield, and 70 min synthesis time from end of bombardment (EOB).
Synthesis and antiherpetic activity of (S)-, (R)- and (±)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'-deoxyguanosine
Ashton,Canning,Reynolds,Tolman,Karkas,Liou,Davies,DeWitt,Perry,Field
, p. 926 - 933 (2007/10/02)
Racemic 9-[2,3-dihydroxy-1-propoxy)methyl]guanine [(±)-iNDG], a new analogue of acyclovir (ACV) and a structural analogue of 2'-nor-2'-deoxyguanosine (2'NDG), was synthesized and found to inhibit the replication of herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). Subsequently, its optical isomers, (R)- and (S)-iNDG, were prepared from chiral intermediates. The chloromethyl ethers of 1,2-di-O-benzyl-D- and -L-glycerol were made and reacted with tris(trimethylsilyl)guanine to give the 9-alkylated guanines, which were deprotected by catalytic hydrogenolysis. Against HSV-1 and HSV-2 in cell culture, (S)-iNDG was approximately 10- to 25-fold more active than the R enantiomer and had an ED50 comparable to those for ACV and 2'NDG. The inferior activity of (R)-iNDG paralleled the poor inhibition of viral DNA polymerase by its phosphorylation products. In mice infected intraperitoneally or orofacially with HSV-1 or intravaginally with HSV-2, (S)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine [(S)-iNDG] was less efficacious than 2'NDG but comparable to or more active than ACV.
Purine acyclic nucleosides. Nitrogen isosteres of 9-[(2-hydroxyethoxy)methyl]guanine as candidate antivirals
Kelley,Krochmal,Schaeffer
, p. 1528 - 1531 (2007/10/02)
A number of nitrogen analogues of 9-[(2-hydroxyethoxy)methyl]guanine [acylovir,Zovirax] containing amine functions in the side chain were synthesized and tested for antiviral activity. These purine acyclic nucleosides were prepared by reaction of tris(trimethylsilyl)guanine or 2,6-diaminopurine sodium salt with the chloromethyl ethers prepared from N-(2-hydroxyethyl)phthalimide,N-[2-(2-hydroxyethoxy)ethyl]phthalimide, or N-(2-hydroxyethyl)oxazolidin-2-one to give the N-blocked intermediates. Deprotection with hydrazine or by alkaline hydrolysis gave 9-[(2-aminoethoxy)methyl]guanine(A), 9-[(2-aminoethoxy)methyl]-2,6-diaminopurine, 9-[[2-(2-aminoethoxy)ethoxy]methyl]guanine, and 9-[[2-[(2-hydroxyethyl)amino]ethoxy]methyl]guanine. When tested against herpes simplex virus type 1, only (A) was active with an IC50 = 8 μM. Little or no activity was observed against a range of other DNA and RNA viruses.
