1214-39-7Relevant articles and documents
Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter
Lougiakis, Nikolaos,Gavriil, Efthymios-Spyridon,Kairis, Markelos,Sioupouli, Georgia,Lambrinidis, George,Benaki, Dimitra,Krypotou, Emilia,Mikros, Emmanuel,Marakos, Panagiotis,Pouli, Nicole,Diallinas, George
, p. 5941 - 5952 (2016)
In the course of our study on fungal purine transporters, a number of new 3-deazapurine analogues have been rationally designed, based on the interaction of purine substrates with the Aspergillus nidulans FcyB carrier, and synthesized following an effective synthetic procedure. Certain derivatives have been found to specifically inhibit FcyB-mediated [3H]-adenine uptake. Molecular simulations have been performed, suggesting that all active compounds interact with FcyB through the formation of hydrogen bonds with Asn163, while the insertion of hydrophobic fragments at position 9 and N6 of 3-deazaadenine enhanced the inhibition.
Structure-based design, synthesis, and antimicrobial activity of purine derived SAH/MTA nucleosidase inhibitors
Tedder, Martina E.,Nie, Zhe,Margosiak, Stephen,Chu, Shaosong,Feher, Victoria A.,Almassy, Robert,Appelt, Krzysztof,Yager, Kraig M.
, p. 3165 - 3168 (2004)
The structure-based design, synthesis, and biological activity of novel inhibitors of S-adenosyl homocysteine/methylthioadenosine (SAH/MTA) nucleosidase are described. Using 6-substituted purine and deaza purines as the core scaffolds, a systematic and structure guided series of modifications provided low nM inhibitors with broad-spectrum antimicrobial activity.
N6-isopentenyladenosine a new potential anti-angiogenic compound that targets human microvascular endothelial cells in vitro
Castiglioni, Sara,Romeo, Valentina,Casati, Silvana,Ottria, Roberta,Perrotta, Cristiana,Ciuffreda, Pierangela,Maier, Jeanette A. M.
, p. 533 - 545 (2018)
N6-isopentenyladenosine is an anti-proliferative and pro-apoptotic atypical nucleoside for normal and tumor cells. Considering the role of angiogenesis in various diseases, we investigated the cytotoxic effect of N6-isopentenyladenosine on human microvascular endothelial cells, protagonists in angiogenesis. Our results show that N6-isopentenyladenosine induced a significant reduction of cell viability, upregulated p21 and promoted caspase-3 cleavage in a dose dependent manner leading to apoptotic cell death as detected by FACS analysis. To understand structure-function relationship of N6-isopentenyladenosine, we investigated the effect of some N6-isopentenyladenosine analogs. Our results suggest that N6-isopentenyladenosine and some of its derivatives are potentially novel angiostatic agents and might be associated with other anti-angiogenic compounds for a better outcome.
Mechanism of formation of N2-benzylguanine in the reaction of 2-amino- 6-chloropurine with sodium benzyl oxide, and benzylation of nucleic acid bases
Koyama, Ken-Ichi,Hitomi, Kenichi,Terashima, Isamu,Kohda, Kohfuku
, p. 1395 - 1399 (1996)
The mechanism of formation of N2-benzylguanine in the reaction of 2- amino-6-chloropurine with a large excess (12-13 molar eq) of sodium benzyl oxide in benzyl alcohol at 130°C was studied. N2,O6-Dibenzylguanine, a reaction intermediate, was isolated and a possible mechanism for its formation is discussed. Furthermore, using this sodium benzyl oxide system, benzylation at the amino group of nucleic acid bases was facilitated.
Reactions of Adenine and Its N-Exo Substituted Analogues with Phenyl Glycidyl Ether
Neporozhneva,Studentzsov,Ramsh
, p. 2248 - 2254 (2021/02/12)
Abstract: The features of reactions of adenine with phenyl glycidyl ether depending on the solvent nature were studied. In DMF in the presence of K2CO3, an N9-alkyl derivative, an experimental antiviral drug 9-(2-hydroxy-3-phenoxypropyl)adenine, was formed predominantly. During alkylation in acetic acid, besides N9-, N3-, and N7-alkylation products were also isolated. Alkylation of 6-[alkyl(dialkyl)amino]purines with phenyl glycidyl ether in DMF produced N-exo substituted 9-(2-hydroxy-3-phenoxypropyl)adenine analogues.
Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis
Wang, Jian,Li, Yan-Hui,Pan, Song-Cheng,Li, Ming-Fang,Du, Wenting,Yin, Hong,Li, Jing-Hua
supporting information, p. 146 - 153 (2020/03/10)
The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.
6-benayl aminopurine synthetic method
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Paragraph 0020; 0021, (2018/07/30)
The invention discloses a 6-benayl aminopurine synthetic method. The method takes hypoxanthine as a raw material, thionyl chloride is taken as a solvent, phosgene or diphosgene or triphosgene is takenas a chloride agent, 4-dimethylaminopyridine or dialkyl aminopyridine is taken as a catalyst for a reaction, after the reaction is completed, 6-chloropurine is obtained, distilled thionyl chloride and phosgene dissolved in thionyl chloride are completely used for a next reaction, and then the obtained 6-chloropurine and benzylamine are subjected to the reaction to synthesize 6-benayl aminopurineunder existence of triethylamine. During a reaction process, the used chloride agent solid triphosgene is completely decomposed to the phosgene dissolved in the solvent under existence of the catalyst4-dimethylaminopyridine, and no solid constituent is residual.
Chemoenzymatic synthesis of cytokinins from nucleosides: Ribose as a blocking group
Oslovsky, Vladimir E.,Solyev, Pavel N.,Polyakov, Konstantin M.,Alexeev, Cyril S.,Mikhailov, Sergey N.
, p. 2156 - 2163 (2018/03/26)
Nucleoside phosphorylases are involved in the salvage pathways of nucleoside biosynthesis and catalyze the reversible reaction of a nucleobase with α-d-ribose-1-phosphate to yield a corresponding nucleoside and an inorganic phosphate. The equilibrium of these reactions is shifted towards nucleosides, especially in the case of purines. Purine nucleoside phosphorylase (PNP, EC 2.4.2.1) is widely used in labs and industry for the synthesis of nucleosides of practical importance. Bacterial PNPs have relatively broad substrate specificity utilizing a wide range of purines with different substituents to form the corresponding nucleosides. To shift the reaction in the opposite direction we have used arsenolysis instead of phosphorolysis. This reaction is irreversible due to the hydrolysis of the resulting α-d-ribose-1-arsenate. As a result, heterocyclic bases are formed in quantitative yields and can be easily isolated. We have developed a novel method for the preparation of cytokinins based on the enzymatic cleavage of the N-glycosidic bond of N6-substituted adenosines in the presence of PNP and Na2HAsO4. According to the HPLC analysis the conversion proceeds in quantitative yields. In the proposed strategy the ribose residue acts as a protective group. No contamination of the final products with AsO43- has been detected via HPLC-HRMS; simple analytical arsenate detection via ESI-MS has been proposed.
Method for synthesizing adenine and derivatives thereof
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Paragraph 0051; 0052, (2017/07/19)
The invention discloses a method for synthesizing adenine and derivatives thereof. The method comprises the steps: firstly, subjecting diethyl malonate and dimethyl dioxirane to an oxidation reaction, so as to obtain 2-hydroxyldiethyl malonate; then, carrying out an ammonolysis reaction with ammonia water, so as to obtain 2-hydroxyl malonamide; then, carrying out a cyclization reaction with trimethyl orthoformate, so as to obtain 5-hydroxyl pyrimid-4,6-(1H,5H)-dione; then, carrying out a chlorination reaction with phosgene, so as to obtain 4,5,6-trichloropyrimidine; then, carrying out a cyclization reaction with formamidine hydrochloride, so as to obtain 4-chloro-1H-pyrazol[3, 4-d]pyrimidine; finally, carrying out an ammoniation reaction with ammonia water or an amine compound in the presence of triethylamine, thereby obtaining the adenine and derivatives thereof. According to the method, the raw materials are moderately-priced and readily available, the reaction conditions are mild, the reaction process is safe, the requirements on production equipment are low, particularly, the environmental pollution is light, and the yield is relatively high, so that the method is applicable to industrial large-scale production.
Preparation method of 6-benzylaminopurine
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Paragraph 0021; 0023; 0025; 0028; 0031; 0034; 0037, (2018/03/24)
The invention relates to a preparation method of 6-benzylaminopurine and belongs to the technical field of pesticide synthesis. Aiming at solving the problems that an existing reaction route is long and the quality is poor, the invention provides the preparation method of the 6-benzylaminopurine. The method comprises the following steps: in the presence of a compound catalyst of I2, P2O5 and ZnCl2, enabling hypoxanthine and benzylamine to react in an N,N-dimethylformamide solvent under the condition that the temperature is 50 DEG C to 75 DEG C; regulating the pH (Potential of Hydrogen) value to be neutral to obtain a product, wherein the mass ratio of the hypoxanthine to the compound catalyst is 1 to (0.3 to 0.5); the mass ratio of the P2O5 to the ZnCl2 to the I2 is 1 to (0.2 to 0.3) to (0.01 to 0.02). According to the preparation method provided by the invention, a DMF (Dimethyl Formamide)-P2O5-ZnCl2-I2 compound catalysis system can be formed and has a synergistic effect to finish a one-step method; the preparation method has the advantage that the reaction route is short and can also have the effect of relatively high yield and product purity.
