Category: 97845-58-4

Wang, Ji-Quan published the artcileNovel radiosynthesis of PET HSV-tk gene reporter probes [¹⁸F]FHPG and [¹⁸F]FHBG employing dual Sep-Pak SPE techniques, Recommanded Product: 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, the publication is Bioorganic & Medicinal Chemistry Letters (2003), 13(22), 3933-3938, database is CAplus and MEDLINE.

Positron emission tomog. (PET) herpes simplex virus thymidine kinase (HSV-tk) gene reporter probes 9-[(3-[¹⁸F]fluoro-1-hydroxy-2-propoxy)methyl]guanine ([¹⁸F]FHPG) [(I); X = O] and 9-(4-[¹⁸F]fluoro-3-hydroxymethylbutyl)guanine ([¹⁸F]FHBG) [I; X = CH₂] 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% radiochem. yield.

Bioorganic & Medicinal Chemistry Letters published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H6BrClO2, Recommanded Product: 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wang, En-si published the artcileSynthesis of a new antiviral medicine famciclovir, Product Details of C8H15BrO2, the publication is Jilin Daxue Ziran Kexue Xuebao (2000), 95-98, database is CAplus.

The title compound was prepared with 21 % yield via regioselective alkylation of 2-aminopurine with 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxan as a pivotal step. The route without highly toxic reagents and high presure and temperature may be applied to industrial production

Jilin Daxue Ziran Kexue Xuebao published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C10H14N2O, Product Details of C8H15BrO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Zheng, Qi-Huang published the artcileAn Improved Total Synthesis of PET HSV-tk Gene Reporter Probe 9-(4-[18F]Fluoro-3-hydroxymethylbutyl)guanine ([18F]FHBG), Formula: C8H15BrO2, the publication is Synthetic Communications (2004), 34(4), 689-704, database is CAplus.

An improved total synthesis of [18F]FHBG (I) starting from triethyl-1,1,2-ethanetricarboxylate and 2-amino-6-chloropurine is reported. [18F]FHBG 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 20-25% radiochem. yield.

Synthetic Communications published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C9H4F6O, Formula: C8H15BrO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Grote, Michaela published the artcileSyntheses of novel modified acyclic purine and pyrimidine nucleosides as potential substrates of herpes simplex virus type-1 thymidine kinase for monitoring gene expression, Safety of 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, the publication is Canadian Journal of Chemistry (2004), 82(4), 513-523, database is CAplus.

Suicide gene therapy with the herpes simplex virus type-1 thymidine kinase gene (HSV-1 tk) is considered to be a promising approach to the treatment of cancer. Making use of the lower specificity of the viral enzyme compared to human thymidine kinase, the therapy involves the administration of antiviral agents (e.g., ganciclovir) as prodrugs to induce enzymic cell death in those cells that express the transferred gene. ¹⁸F-labeled derivatives have been described for monitoring location, duration, and magnitude of the viral kinase enzyme activity by positron emission tomog. (PET). Since an optimal radiotracer has not been developed, novel substances were synthesized for monitoring gene expression. A group of 13 nucleoside analogs were synthesized, among them N¹-methyl-9-[(1,3-dihydroxy-2-propoxy)methyl]guanine and N¹-methyl-9-[(4-hydroxy)-3-hydroxymethylbutyl]guanine as Me analogs of ganciclovir and penciclovir and their related fluoro compounds Further novel derivatives include N⁶-methyl-9-[(1,3-dihydroxy-2-propoxy)methyl]-, N⁶-methyl-9-[(4-hydroxy)-3-hydroxymethylbutyl]adenine, as well as the uracil derivatives 5-hydroxy-1-[(1,3-dihydroxy-2-propoxy)methyl]uracil, 6-methyl-1-[(1,3-dihydroxy-2-propoxy)-methyl]uracil, and its 3-fluoro-derivative

Canadian Journal of Chemistry published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H15BrO2, Safety of 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Kim, Choung Un published the artcileA new class of acyclic phosphonate nucleotide analogs: Phosphonate isosteres of acyclovir and ganciclovir monophosphates as antiviral agents, Product Details of C8H15BrO2, the publication is Journal of Medicinal Chemistry (1991), 34(7), 2286-94, database is CAplus and MEDLINE.

Novel phosphonate isosteres of acyclovir (ACV) and ganciclovir (DHPG) monophosphates I (R = H, CH₂OH) were found to be potent and selective antiherpesvirus agents. In the series of phosphonate analogs of ACV monophosphate, only the guanine analog I (R = H) exhibited activity against herpesviruses, similar to the structure-activity relationship observed for base modification of ACV analogs. The phosphonate isostere of ACV monophosphate I (R = H) was more effective than ACV in the HSV-1 infected mouse model. The 3′-carba analog of 9-[3-hydroxy-2-(phosphonomethoxy)propyl]purines/ pyrimidines (adenine:HPMPA; guanine:HPMPG; cytosine:HPMPC) are devoid of antiherpesvirus activity. This result confirms that the β-oxygen atom of the phosphonomethyl ether functionality in HPMP-purines/pyrimidines plays a critical role for activity against herpesviruses. The crystal structure of [(benzoyloxy)methoxy]methyladenine II was determined

Journal of Medicinal Chemistry published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H15BrO2, Product Details of C8H15BrO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Khudolei, V. V. published the artcileThe study of mutagenic activity of carcinogens and other chemical agents with Salmonella typhimurium assays: testing of 126 compounds, Quality Control of 97845-58-4, the publication is Archiv fuer Geschwulstforschung (1987), 57(6), 453-62, database is CAplus and MEDLINE.

A total of 126 chem. compounds were tested in the Ames assay with S. typhimurium of 8 various strains (mainly TA98 + TA100). For metabolic activation liver S₉ from arochlor-treated rats was used. In the first group of substances tested (51 compounds with confirmed carcinogenicity for animals) 45 agents possessed mutagenicity and 6 gave false-neg. response (1,2-dimethylhydrazine, urethane, DDT, chloroform, carbon tetrachloride, 1,4-dioxane). In group 2 (27 compounds which did not possess carcinogenic activity) 22 agents were correctly identified and the other 5 gave false-pos. responses (acrolein, styrene oxide, acridine orange, 1-naphthylamine, dichloromethane). After summation of data obtained, test sensitivity for both groups together made 88.2%; specificity 81.5% and predictive value 90%. In group 3 (48 compounds, presented by chem., pharmaceutical and food industries, for which either there are insufficient data on their carcinogenicity, or they were tested for the first time), 8 appeared mutagenic (1-aminoanthraquinone, 2-aminoanthraquinone, 1-amino-4-chloroanthraquinone, 2-amino-3-oxyanthraquinone, Rhoduline blue 5B, dinitrochlorbenzene, nitrosodiphenylamine and 2,3,5-trinitronaphthalene).

Archiv fuer Geschwulstforschung published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H15BrO2, Quality Control of 97845-58-4.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Harnden, M. R. published the artcileAn improved synthesis of the antiviral acyclonucleoside 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine, Product Details of C8H15BrO2, the publication is Tetrahedron Letters (1985), 26(35), 4265-8, database is CAplus.

Alkylation of 2-amino-6-chloropurine with 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxane and subsequent acid hydrolysis provides an improved procedure for synthesis of the antiviral title acyclonucleoside I.

Tetrahedron Letters published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H15BrO2, Product Details of C8H15BrO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Harnden, Michael R. published the artcileSynthesis and antiviral activity of 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purines, Recommanded Product: 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, the publication is Journal of Medicinal Chemistry (1987), 30(9), 1636-42, database is CAplus and MEDLINE.

Alkylation of 2-amino-6-chloropurine with 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxane provided 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (I) in high yield. I was readily converted to the antiviral acyclonucleoside II [R = NH₂, R¹ = R² = H (III)] and to its 6-chloro, 6-thio, 6-alkoxy, 6-amino, and 6-deoxy purine analogs. III was also converted to its xanthine analog. Similarly, alkylation of 6-chloropurine provided a route to II (R = R¹ = R² = H).. Of these 9-substituted purines, III showed the highest activity against herpes simplex virus types 1 and 2 in cell cultures, and in some tests it was more active than acyclovir, with no evidence of toxicity for the cells. A series of monoesters and diesters of III were prepared, and some of these also showed antiherpes virus activity in cell cultures, the most active ester being the dihexanoate II [R = NH₂, R¹ = R² = Me(CH₂)₄CO].

Journal of Medicinal Chemistry published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H15BrO2, Recommanded Product: 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Fuchigami, Takeshi published the artcileSynthesis and Characterization of 9-(4-[¹⁸F]Fluoro-3-(hydroxymethyl)butyl)-2-(phenylthio)-6-oxopurine as a Novel PET Agent for Mutant Herpes Simplex Virus Type 1 Thymidine Kinase Reporter Gene Imaging, Name: 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, the publication is Molecular Imaging and Biology (2020), 22(5), 1151-1160, database is CAplus and MEDLINE.

Purpose: [¹⁸F]FHBG has been used as a positron emission tomog. (PET) imaging tracer for the monitoring of herpes simplex virus type 1 thymidine kinase (HSV1-tk), a reporter gene for cell and gene therapy in humans. However, this tracer shows inadequate blood-brain barrier (BBB) penetration and, therefore, would be limited for accurate quantification of reporter gene expression in the brain. Here, we report the synthesis and evaluation of 9-(4-[¹⁸F]fluoro-3-(hydroxymethyl)butyl)-2(phenylthio)-6-oxopurine ([18F]FHBT) as a new PET tracer for imaging reporter gene expression of HSV1-tk and its mutant HSV1-sr39tk, with the aim of improved BBB penetration. Procedures: [¹⁸F]FHBT was prepared by using a tosylate precursor and [18F]KF. The cellular uptake of [¹⁸F]FHBT was performed in HSV1-sr39tk-pos. (+) or HSV1-sr39tk-neg. (-) MDA-MB-231 breast cancer cells. The specificity of [¹⁸F]FHBT to assess HSV1-sr39tk expression was evaluated by in vitro blocking studies using 1 mM of ganciclovir (GCV). Penetration of [¹⁸F]FHBT and [¹⁸F]FHBG across the BBB was assessed by dynamic PET imaging studies in normal mice. Results: The tosylate precursor reacted with [¹⁸F]KF using Kryptofix2.2.2 followed by deprotection to give [¹⁸F]FHBT in 10 % radiochem. yield (decay-corrected). The uptake of [¹⁸F]FHBT in HSV1-sr39tk (+) cells was significantly higher than that of HSV1-sr39tk (-) cells. In the presence of GCV (1 mM), the uptake of [¹⁸F]FHBT was significantly decreased, indicating that [¹⁸F]FHBT serves as a selective substrate of HSV1-sr39TK. PET images and time-activity curves of [¹⁸F]FHBT in the brain regions showed similar initial brain uptakes (∼12.75 min) as [¹⁸F]FHBG (P > 0.855). Slower washout of [¹⁸F]FHBT was observed at the later time points (17.75 – 57.75 min, P > 0.207). Conclusions: Although [¹⁸F]FHBT showed no statistically significant improvement of BBB permeability compared with [¹⁸F]FHBG, we have demonstrated that the 2-(phenylthio)-6-oxopurine backbone can serve as a novel scaffold for developing HSV1-tk/HSV1-sr39tk reporter gene imaging agents for addnl. research in the future.

Molecular Imaging and Biology published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H15BrO2, Name: 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Hou, Rui-zhen published the artcileHydrolysis of 5-(2-haloethyl)-1,3-dioxolanes, COA of Formula: C8H15BrO2, the publication is Jilin Daxue Ziran Kexue Xuebao (2000), 94-95, database is CAplus.

Three different kinds of 1,3-dioxolane compounds were hydrolyzed in an acidic condition. The results showed that tetrahydro-3-furanmethanol (I) was the main product. For example, hydrolysis of 5-(2-iodoethyl)-1,3-dioxolane with aqueous HCl gave 81% I.

Jilin Daxue Ziran Kexue Xuebao published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H15BrO2, COA of Formula: C8H15BrO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary