1928-76-3Relevant academic research and scientific papers
The alkylation of 6-chloropurine with alcohols by Mitsunobu reaction
Toyota,Katagiri,Kaneko
, p. 1039 - 1041 (1992)
A general procedure has been developed for the preparation of 9-alkylated adenines by the Mitsunobu reaction between 6-chloropurine and several alcohols, followed by the replacement of the chlorine with ammonia. A lesser amount of the 7-alkylpurines was also obtained, irrespective of the alcohol used.
Antiviral properties and interaction of novel chalcone derivatives containing a purine and benzenesulfonamide moiety
Zhou, Dagui,Xie, Dandan,He, Fangcheng,Song, Baoan,Hu, Deyu
, p. 2091 - 2097 (2018)
A new concise and facile method was explored to synthesize a series of novel chalcone derivatives containing a purine and benzenesulfonamide moiety and their antiviral properties were evaluated against TMV and CMV. Biological assays indicated that several
Regioselective alkylation reaction of purines under microwave irradiation
Ginard, Jaume,Jahani, Daniel,Mur, Nuria,Pujol, Maria Dolors,Vi?as, Miquel,Vinuesa, Arturo
, (2021/12/22)
The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylati
Synthesis of novel selenotetrazole purine derivatives and their potential chemotherapeutic activities
Dilek, Gulay,Tekin, Ishak Ozel,Coban, Burak,Disli, Ali,Gercek, Zuhal
, p. 84 - 97 (2020/10/08)
The development of novel chemotherapeutic agents is indispensable to improve cancer treatment. One of the conventional approaches toward the synthesis of anticancer agents is the design of a compound whose structure is similar to purines found in DNA. In this study, a series of novel artificial purine nucleosides bearing selenotetrazole pharmacophore, 4a–4h, were synthesized. In order to get preliminary information about their cytotoxic activities, the interaction of compounds with DNA was investigated by UV titration and agarose gel electrophoresis and transcription inhibition studies were performed. The cytotoxic effects of the compounds against B16 melanoma, OV90 ovarian cancer, JM1 lymphoma cell lines, and PHA-induced peripheral blood lymphocytes were also investigated. In cell assay studies, the effects of the compounds on synthesis and mitosis stage of cell cycle were compared by flow cytometry. Although none of the compounds synthesized interacted with DNA and exhibited transcription inhibition, all of them significantly inhibited DNA synthesis phase and showed cytotoxic activity on cancer and proliferating cells. [Figure not available: see fulltext.]
A modular approach for the installation of functionalized phosphonates to heterocycles
Shultz, Zachary,Shan, Chuan,Wojtas, Lukasz,Lopchuk, Justin M.
, p. 73 - 96 (2021/04/09)
Phosphonic acids and esters are pervasive throughout the discovery sciences, from medicine and agriculture, to materials and asymmetric synthesis. The ability to install and construct molecular architecture containing phosphonic functionality has led to t
Purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof
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Paragraph 0030, (2019/01/05)
The invention discloses a purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof. The purine-ring-containing benzene sulfonamide chalcone derivative has a formula (I) shown as below, in which R1 is 4-oxymethyl, 4-tert-butyl, 4-methyl, 4-flouride, 4-bromide, 2-methyl, 2-fluoride, 2-chloride, 2-bromide and hydrogen atom and R2 is methyl, ethyland benzyl. The purine-ring-containing benzene sulfonamide chalcone derivative can inhibit tobacco mosaic virus, cucumber mosaic virus, potato Y virus and southern rice black-streaked dwarf virus.
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.
Structure-metabolism relationships in human-AOX: Chemical insights from a large database of aza-aromatic and amide compounds
Lepri, Susan,Ceccarelli, Martina,Milani, Nicolò,Tortorella, Sara,Cucco, Andrea,Valeri, Aurora,Goracci, Laura,Brink, Andreas,Cruciani, Gabriele
, p. E3178 - E3187 (2017/04/24)
Aldehyde oxidase (AOX) is a metabolic enzyme catalyzing the oxidation of aldehyde and aza-aromatic compounds and the hydrolysis of amides, moieties frequently shared by the majority of drugs. Despite its key role in human metabolism, to date only fragmentary information about the chemical features responsible for AOX susceptibility are reported and only "very local" structure-metabolism relationships based on a small number of similar compounds have been developed. This study reports a more comprehensive coverage of the chemical space of structures with a high risk of AOX phase I metabolism in humans. More than 270 compounds were studied to identify the site of metabolism and themetabolite(s). Both electronic [supported by density functional theory (DFT) calculations] and exposure effects were considered when rationalizing the structure-metabolism relationship.
The Convenient Synthesis of Unsaturated Nucleoside Analogues in Water under Microwave Irradiation
Xia, Ran,Sun, Li-Ping
, p. 76 - 82 (2016/03/01)
A convenient method for the regioselective synthesis of unsaturated nucleoside analogs in water under microwave irradiation was developed. All pyrimidine and purine nucleoside derivatives were exclusively alkylated at N1 and N9 respectively in good to excellent yields. In addition, this system could tolerate a broad range of functional groups, such as chloro, bromo, iodo, alkyl, amino, and hydroxyl groups. More importantly, the reaction scale could be enlarged to 50 mmol which made this route attractive for industrial application.
8-Bromination of 2,6,9-trisubstituted purines with pyridinium tribromide
Bliman, David,Pettersson, Mariell,Bood, Mattias,Gr?tli, Morten
supporting information, p. 2929 - 2931 (2014/05/06)
2,6,9-Trisubstituted purines are brominated in high yields using pyridinium tribromide as the brominating reagent. This procedure works excellently for electron-rich purines having electron-donating substituents at the 2- and 6-positions. The use of pyridinium tribromide, a crystalline alternative to elemental bromine, improves the bromination procedure for this type of substrate as the reagent is easy to handle and the work-up and purification procedures are simplified.
