91366-99-3Relevant academic research and scientific papers
Decatungstate-Mediated C(sp3)–H Heteroarylation via Radical-Polar Crossover in Batch and Flow
Capaldo, Luca,Frederick, Michael O.,García-Losada, Pablo,Laudadio, Gabriele,Mateos, Carlos,No?l, Timothy,Nu?o, Manuel,Nyuchev, Alexander V.,Rincón, Juan A.,Wan, Ting
supporting information, p. 17893 - 17897 (2021/07/14)
Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)–H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative radical–polar crossover concept to access the direct net-oxidative C(sp3)–H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (?)-ambroxide, podophyllotoxin, and dideoxyribose.
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.
C-H amination of purine derivatives via radical oxidative coupling
Luo, Zheng,Jiang, Ziyang,Jiang, Wei,Lin, Dongen
, p. 3710 - 3718 (2018/04/14)
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.
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.
APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT
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Paragraph 0238; 0239, (2018/10/27)
PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT
N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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Paragraph 0490, (2013/03/26)
The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
Copper-catalyzed N-alkoxyalkylation of nucleobases involving direct functionalization of sp3 CeH bonds adjacent to oxygen atoms
Huang, Rui,Xie, Chunsong,Huang, Lin,Liu, Jinhua
, p. 577 - 582 (2013/07/25)
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
Guo, Hai-Ming,Xia, Chao,Niu, Hong-Ying,Zhang, Xiao-Ting,Kong, Si-Nan,Wang, Dong-Chao,Qu, Gui-Rong
supporting information; experimental part, p. 53 - 56 (2011/03/22)
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
Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives
Szuecova, Lucie,Spichal, Lukas,Dolezal, Karel,Zatloukal, Marek,Greplova, Jarmila,Galuszka, Petr,Krystof, Vladimir,Voller, Jiri,Popa, Igor,Massino, Frank J.,Jorgensen, Jan-Elo,Strnad, Miroslav
experimental part, p. 1938 - 1947 (2009/05/26)
In an attempt to improve specific biological functions of cytokinins routinely used in plant micropropagation, 33 6-benzylamino-9-tetrahydropyran-2-ylpurine (THPP) and 9-tetrahydrofuran-2-ylpurine (THFP) derivatives, with variously positioned hydroxy and methoxy functional groups on the benzyl ring, were prepared. The new derivatives were prepared by condensation of 6-chloropurine with 3,4-dihydro-2H-pyran or 2,3-dihydrofuran and then by the condensation of these intermediates with the corresponding benzylamines. The prepared compounds were characterized by elemental analyses, TLC, HPLC, melting point determinations, CI+ MS and 1H NMR spectroscopy. The cytokinin activity of all the prepared derivatives was assessed in three classical cytokinin bioassays (tobacco callus, wheat leaf senescence and Amaranthus bioassay). The derivatives 6-(3-hydroxybenzylamino)-9-tetrahydropyran-2-ylpurine (3) and 6-(3-hydroxybenzylamino)-9-tetrahydrofuran-2-ylpurine (23) were selected, because of the high affinity of their parent compound meta-topolin (mT, 6-(3-hydroxybenzylamino)purine) to cytokinin receptors, as model compounds for studying their perception by the receptors CRE1/AHK4 and AHK3 in a bacterial assay. Both receptors perceived these two derivatives less well than they perceived the parent compound. Subsequently, the susceptibility of several new derivatives to enzyme degradation by cytokinin oxidase/dehydrogenase was studied. Substitution of tetrahydropyran-2-yl (THP) at the N9 position decreased the turnover rates of all new derivatives to some extent. To provide a practical perspective, the cytotoxicity of the prepared compounds against human diploid fibroblasts (BJ) and the human cancer cell lines K-562 and MCF-7 was also assayed in vitro. The prepared compounds showed none or marginal cytotoxicity compared to the corresponding N9-ribosides. Finally, the pH stability of the two model compounds was assessed in acidic and neutral water solutions (pH 3-7) by high-performance liquid chromatography (HPLC).
6,9-Disubstituted Purine Derivatives and Their Use as Cosmetics and Cosmetic Compositions
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Page/Page column 8-9, (2009/07/17)
Certain 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are provided. These 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are useful in compositions for treating mammalian cells, and especially human skin cells, in order to ameliorate the adverse effects of aging, treat skin disease states, treat immunological responses resulting from or associated with inflammation, and the like.
