90348-54-2Relevant articles and documents
N-9 Alkylation of purines via light-promoted and metal-free radical relay
Mao, Runze,Sun, Lifeng,Wang, Yong-Shi,Zhou, Min-Min,Xiong, De-Cai,Li, Qin,Ye, Xin-Shan
supporting information, p. 61 - 64 (2017/09/06)
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.
Halogen-Bond-Promoted α-C?H Amination of Ethers for the Synthesis of Hemiaminal Ethers
Pan, Zhangjin,Fan, Zhenwei,Lu, Beili,Cheng, Jiajia
supporting information, p. 1761 - 1767 (2018/03/21)
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.).
New cytokinin derivatives possess UVA and UVB photoprotective effect on human skin cells and prevent oxidative stress
H?nig, Martin,Plíhalová, Lucie,Spíchal, Luká?,Grúz, Ji?í,Kadlecová, Alena,Voller, Ji?í,Svobodová, Alena Rajnochová,Vostálová, Jitka,Ulrichová, Jitka,Dole?al, Karel,Strnad, Miroslav
, p. 946 - 957 (2018/04/02)
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.
