90348-54-2

Usage

Purine derivative

Yes, as it is a purine analogue

Chlorine atoms

Two, located at the 2 and 6 positions of the purine ring

Tetrahydrofuran-2-yl group

Attached at the 9 position

Biological activity

Potential, but requires further study

Pharmaceutical and medicinal research

May be used in, but further studies are needed

Modulation of protein-protein interactions

Possible, related to purine metabolism or other biological processes

Structure importance

Contributes to its biological and pharmacological properties

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 5451-40-1 2,6 dichloropurine 
• 109-99-9 tetrahydrofuran 

Downstream Products

• 110085-38-6 6-(N⁴-phenylpiperazin-1-yl)-2-methoxy-9-(2-tetrahydrofuranyl)-9H-purine 
• 110085-45-5 6-(N⁴-phenylpiperazin-1-yl)-2-chloro-9-(2-tetrahydrofuranyl)-9H-purine 

Relevant academic research and scientific papers

N-9 Alkylation of purines via light-promoted and metal-free radical relay

A metal-free and light-promoted approach to the synthesis of N-9 alkylated purine nucleoside derivatives, via a CF3 radical triggered radical relay pathway, has been developed. Purine nucleoside derivatives were prepared regioselectively in good to high yields. Photosensitizers and metals are free in this transformation. Visible light or even sunlight can be used as the source of light for the reactions.

C-H amination of purine derivatives via radical oxidative coupling

An oxidative coupling reaction between purines and alkyl ethers/benzyl compounds was developed to synthesize a series of N9 alkylated purine derivatives using n-Bu4NI as a catalyst and t-BuOOH as an oxidant. This protocol uses commercially available, inexpensive catalysts and oxidants and has a wide range of substrates with a simple operation.

Halogen-Bond-Promoted α-C?H Amination of Ethers for the Synthesis of Hemiaminal Ethers

A simple halogen-bond-promoted α-C?H amination of ether/thioether with a variety of N?H compounds has been accomplished. In the presence of low-cost and readily available perfluorobutyl iodide, a diverse range of hemiaminal ether derivatives, including the valuable hydrazone hemiaminal ethers, were quickly assembled under thermal or visible-light irradiation conditions. Mechanistic studies suggest that a halogen-bond adduct was formed and a radical chain pathway might be operative. Synthetic application of the method has been demonstrated via the preparation of the anti-viral and anti-tumor drug, Tegafur. (Figure presented.).

9-(2-OXACYCLOALKYL)-9H-PURINE-2,6-DIAMINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF SKIN DISORDERS

The invention relates to N22,N66-disubstituted-9-(2-oxacycloalkyl)-9H-purine-2,6-diamine derivatives and their use as drugs and cosmetics. The compounds of the present invention exhibit a number of biological activities associated with oxidative stress inhibition, especially anti-aging, anti-inflammatory and anti-neurodegenerative biological activities. The invention also relates to cosmetic and pharmaceutical compositions containing such derivatives as active agents.

New cytokinin derivatives possess UVA and UVB photoprotective effect on human skin cells and prevent oxidative stress

Eleven 6-furfurylaminopurine (kinetin, Kin) derivatives were synthesized to obtain biologically active compounds. The prepared compounds were characterized using 1H NMR, mass spectrometry combined with HPLC purity determination and elemental C, H, N analyses. The biological activity of new derivatives was tested on plant cells and tissues in cytokinin bioassays, such as tobacco callus, detached wheat leaf chlorophyll retention bioassay and Amaranthus bioassay. The selected compounds were subsequently tested on normal human dermal fibroblasts (NHDF) and keratinocyte cell lines (HaCaT) to exclude possible phototoxic effects and, on the other hand, to reveal possible UVA and UVB photoprotective activity. The protective antioxidant activity of the prepared cytokinin derivatives was further studied and compared to previously prepared antisenescent compound 6-furfurylamino-9-(tetrahydrofuran-2-yl)purine (Kin-THF) using induced oxidative stress (OS) on nematode Caenorhabditis elegans damaged by 5-hydroxy-1,4-naphthoquinone (juglone), a generator of reactive oxygen species. The observed biological activity was interpreted in relation to the structure of the prepared derivatives. The most potent oxidative stress protection of all the prepared compounds was shown by 6-(thiophen-2-ylmethylamino)-9-(tetrahydrofuran-2-yl)purine (6) and 2-chloro-6-furfurylamino-9-(tetrahydrofuran-2-yl)purine (9) derivatives and the results were comparable to Kin-THF. Compounds 6 and 9 were able to significantly protect human skin cells against UV radiation in vitro. Both the derivatives 6 and 9 showed higher protective activity in comparison to previously known structurally similar compounds Kin and Kin-THF. The obtained results are surprising due to the fact that the prepared compounds showed to be inactive in the ORAC assay which proved that the compounds did not act as direct antioxidants as they were unable to directly scavenge oxygen radicals.

L-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers

An efficient and regioselective synthesis of N-9 alkoxyalkylated purine nucleoside derivatives was achieved via the N-alkoxyalkylation of purine rings with vinyl ethers catalyzed by l-ProT. The advantages of this protocol include good to excellent yield,

Copper-catalyzed N-alkoxyalkylation of nucleobases involving direct functionalization of sp3 CeH bonds adjacent to oxygen atoms

N-Alkoxyalkylation of nucleobases was realized by the copper-catalyzed peroxide-promoted coupling of nucleobases with readily available saturated ethers. Both purines and pyrimidines could be N-alkoxyalkylated through this method in moderate to good yields. 2D-NMR revealed that N9-alkoxyalkylation preferentially occurred when purines were used in this reaction. Crown Copyright

Intermolecular hydrogen abstraction reaction between nitrogen radicals in purine rings and alkyl ethers: A highly selective method for the synthesis of N-9 alkylated purine nucleoside derivatives

A highly selective method for the synthesis of N-9 alkylated purine nucleoside derivatives via an intermolecular hydrogen abstraction reaction between nitrogen radicals in purine rings and alkyl ethers was developed. Novel purine nucleoside derivatives we

SUBSTITUTED ADENINES AND THE USE THEREOF

This invention relates to compounds of Formula (I): and their use in the treatment of bacterial infections.

Studies in Nucleosides: Part XIV - Synthesis of 2-Chloro/methoxy-6-N-substituted-9-(2-tetrahydrofuranyl)-9H-purines and Their Biological Activity

2-Methoxy-6-N-substituted-9-(2-tetrahydrofuranyl)-9H-purines (3-8) and 2-chloro-6-N-substituted-9-(2-tetrahydrofuranyl)-9H-purines (9-16) have been synthesised and screened against the semliki forest virus in Swiss albino mice.The compounds 3, 11 and 13 i