2140-11-6Relevant academic research and scientific papers
Stereoselective deamination of (5′RS)-5′-methyl-2′,3′-isopropylidene adenosine catalyzed by adenosine deaminase: Preparation of diastereomerically pure 5′-methyl adenosine and inosine derivatives
Ciuffreda, Pierangela,Loseto, Angela,Santaniello, Enzo
, p. 239 - 241 (2002)
Adenosine deaminase from calf intestine catalyzes the stereoselective deamination of (5′S)-5′-methyl-2′,3′-isopropylidene adenosine to the corresponding inosine derivative, so that by enzymatic deamination of (5′RS)-5′-methyl-2′,3′-isopropylidene adenosin
A novel method for the synthesis of sulfur substituted-cyclopyrophosphate of cADPR analogs
Wu, Ren-Min,Qi, Na,Jia, Yu-Wen,Guan, Zhu,Zhang, Liang-Ren,Zhang, Li-He,Yang, Zhen-Jun
, p. 1583 - 1585 (2014)
A facile and efficient protocol for the synthesis of sulfur substituted-cyclopyrophosphate of cIDPRE (PS1-cIDPRE) was developed. The key step was the cyclization process which was completed by the sulfur substituted cyclization precursor 1b via the one-pot phosphoramidite strategy.
Facile synthesis of N-6 adenosine modified analogue toward S-adenosyl methionine derived probe for protein arginine methyltransferases
Hong, Wei,Dowden, James
, p. 1439 - 1442 (2011)
Chemically modified cellular co-factors that provide function, such as immobilization or incorporation of fluorescent dyes, are valuable probes of biological activity. A convenient route to obtain S-adenosyl methionine (AdoMet) analogues modified at N-6 adenosine to feature a linker terminating in azide functionality is described herein. Subsequent decoration of such AdoMet analogues with guanidinium terminated linkers leads to novel potential bisubstrate inhibitors for protein arginine methyltransferases, PRMTs.
Kinase-Inhibitory Nucleoside Derivatives from the Pacific Bryozoan Nelliella nelliiformis
Bracegirdle, Joe,Gordon, Dennis P.,Harvey, Joanne E.,Keyzers, Robert A.
, p. 547 - 551 (2020/03/19)
Marine organisms are a valuable source of bioactive natural products, yet bryozoan invertebrates have been relatively understudied. Herein, we report nelliellosides A and B, new secondary metabolites of the Pacific bryozoan Nelliella nelliiformis, found using NMR-guided isolation. Their structures, including absolute configurations, were elucidated using spectroscopic and chromatographic techniques. Total synthesis of the natural products and four analogues was also achieved, in addition to an assessment of their biological activity, especially kinase inhibition.
A Structure-Activity Relationship Study of Bitopic N 6-Substituted Adenosine Derivatives as Biased Adenosine A1 Receptor Agonists
Aurelio, Luigi,Baltos, Jo-Anne,Ford, Leigh,Nguyen, Anh T. N.,J?rg, Manuela,Devine, Shane M.,Valant, Celine,White, Paul J.,Christopoulos, Arthur,May, Lauren T.,Scammells, Peter J.
supporting information, p. 2087 - 2103 (2018/03/21)
The adenosine A1 receptor (A1AR) is a potential novel therapeutic target for myocardial ischemia-reperfusion injury. However, to date, clinical translation of prototypical A1AR agonists has been hindered due to dose limiting adverse effects. Recently, we demonstrated that the biased bitopic agonist 1, consisting of an adenosine pharmacophore linked to an allosteric moiety, could stimulate cardioprotective A1AR signaling in the absence of unwanted bradycardia. Therefore, this study aimed to investigate the structure-activity relationship of compound 1 biased agonism. A series of novel derivatives of 1 were synthesized and pharmacologically profiled. Modifications were made to the orthosteric adenosine pharmacophore, linker, and allosteric 2-amino-3-benzoylthiophene pharmacophore to probe the structure-activity relationships, particularly in terms of biased signaling, as well as A1AR activity and subtype selectivity. Collectively, our findings demonstrate that the allosteric moiety, particularly the 4-(trifluoromethyl)phenyl substituent of the thiophene scaffold, is important in conferring bitopic ligand bias at the A1AR.
A new method for synthesis and angiogenic evaluation of leteprinim potassium and its novel analogs
Sakakibara, Norikazu,Tsukamoto, Ikuko,Isono, Yohei,Takata, Maki,Konishi, Ryoji,Kato, Yoshihisa,Maruyama, Tokumi
, p. 2369 - 2384 (2013/11/19)
We developed a novel pathway for the successful synthesis of leteprinim potassium 1, which is one of the candidate substances for treating Alzheimer's disease, and subsequently synthesized 4 types of corresponding novel derivatives 2-5 that have hypoxanthine or 2-chloro-6-aminopurine as the nucleobase. We then determined the angiogenic activity of these compounds by using human umbilical vein endothelial cells. Compounds 1-4 showed no angiogenic potencies judging from statistical analysis, student's t-test.
Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives
Vertuani, Silvia,Baldisserotto, Anna,Varani, Katia,Borea, Pier Andrea,De Marcos Maria Cruz, Bonache,Ferraro, Luca,Manfredini, Stefano,Dalpiaz, Alessandro
supporting information; experimental part, p. 202 - 209 (2012/09/07)
Nucleoside derivatives are largely synthesized and tested to investigate their influence on platelet aggregation. It's well known that P2Y receptors play an important role in the regulation of platelet function and, as consequence, in controlling atherothrombotic events. The research of compounds that antagonize P2Y1 and, in particular, P2Y12 receptors is of great interest in the aim to obtain platelet aggregation inhibitors that are effective in the prevention and treatment of arterial thrombosis. In this study we present the synthesis and in vitro metabolic stability in human blood and rat liver homogenate of a new class of nucleoside derivatives, in particular 5′-phosphonate adenosine, inosine, guanosine and thioadenosine analogues also modified at the ribose moiety. On the basis of the results obtained we can hypothesize compounds 4 and 18 to have in vivo a relatively high stability.
An efficient synthesis of futalosine
Li, Xu,Tanner, Martin E.
supporting information; experimental part, p. 6463 - 6465 (2010/12/25)
Futalosine is a naturally occurring nucleoside comprised of an inosine core with a 3-carboxyphenyl methylene ketone functionality replacing the C-5′ hydroxyl. Recent studies have shown that it is a key intermediate in an alternative biosynthetic pathway that generates menaquinone in a variety of bacterial species. Here we report the first synthesis of futalosine in seven steps from inosine in an overall 17% yield. This work will enable further studies on menaquinone biosynthesis in pathogenic bacteria.
Simple method for fast deprotection of nucleosides by triethylamine- catalyzed methanolysis of acetates in aqueous medium
Meier, Lidiane,Monteiro, Gustavo C.,Baldissera, Rodrigo A.M.,Sa?, Marcus Mandolesi
scheme or table, p. 859 - 866 (2010/09/11)
A straightforward methodology for deacetylation of protected ribonucleosides was developed based on triethylamine-catalyzed solvolysis in aqueous methanol. Reactions are completed in a few minutes under microwave irradiation and the free nucleosides are obtained in high yield after simple evaporation of volatiles. Other important features include the involvement of readily available reagents and the compatibility with diverse functional groups, which make this process very attractive for broad application.
Synthesis and biological evaluation of novel neamine-nucleoside conjugates potentially targeting to RNAs
Xu, Yanli,Jin, Hongwei,Yang, Zhenjun,Zhang, Liangren,Zhang, Lihe
experimental part, p. 5228 - 5239 (2009/12/04)
Eighteen novel neamine-nucleoside conjugates with ethylenediamine-lysine or ethylenediamine-arginine as the linker were synthesized and their potential binding to A site of 16S RNA and TAR RNA was evaluated using SPR (surface plasmon resonance). Compared with neamine, compounds 10i and 10q show 6.3 and 4.8 times potential in binding to A site of 16S RNA and eight and six times potential in binding to TAR RNA, respectively. According to the data of SPR, it indicates that amino acid residue and nucleobase moieties of the designed neamine-nucleosides conjugates exhibit the important contributions for the binding to A site of 16S RNA and TAR RNA. The molecular docking study on the interaction between the ligands and A site of 16S RNA is in agreement with the experimental data. The novel type of modification may provide a promising way for the development of neamine derivatives effectively targeting to RNAs.
