138385-29-2Relevant academic research and scientific papers
Probing binding requirements of NAD kinase with modified substrate (NAD) analogues
Bonnac, Laurent,Chen, Liqiang,Pathak, Rashmi,Gao, Guangyao,Ming, Qian,Bennett, Eric,Felczak, Krzysztof,Kullberg, Martin,Patterson, Steven E.,Mazzola, Francesca,Magni, Giulio,Pankiewicz, Krzysztof W.
, p. 1512 - 1515 (2007)
Synthesis of novel NAD+ analogues that cannot be phosphorylated by NAD kinase is reported. In these analogues the C2′ hydroxyl group of the adenosine moiety was replaced by fluorine in the ribo or arabino configuration (1 and 2, respectively) or was inverted into arabino configuration to give compound 3. Compounds 1 and 2 showed inhibition of human NAD kinase, whereas analogue 3 inhibited both the human and Mycobacterium tuberculosis NAD kinase. An uncharged benzamide adenine dinucleotide (BAD) was found to be the most potent competitive inhibitor (Ki = 90 μM) of the human enzyme reported so far.
Chemoselective and Diastereoselective Synthesis of C-Aryl Nucleoside Analogues by Nickel-Catalyzed Cross-Coupling of Furanosyl Acetates with Aryl Iodides
Li, Chao,Li, Luyang,Li, Yuxi,Shao, Feng,Tian, Xiaoying,Wang, Zheng
supporting information, (2021/11/30)
Canonical nucleosides are vulnerable to enzymatic and chemical degradation, yet their stable mimics—C-aryl nucleosides—have demonstrated potential utility in medicinal chemistry, chemical biology, and synthetic biology, although current synthetic methods remain limited in terms of scope and selectivity. Herein, we report a cross-electrophile coupling to prepare C-aryl nucleoside analogues from readily available furanosyl acetates and aryl iodides. This nickel-catalyzed modular approach is characterized by mild reaction conditions, broad substrate scope, excellent β-selectivity, and high functional-group compatibility. The exclusive chemoselectivity with respect to the aryl iodide enables efficient preparation of a variety of C-aryl halide furanosides suitable for various downstream transformations. The practicality of this transformation is demonstrated through the synthesis of a potent analogue of a naturally occurring NF-κB activator.
Chemical Proteomics Approach for Profiling the NAD Interactome
?ileikyt?, Justina,Sundalam, Sunil,David, Larry L.,Cohen, Michael S.
, p. 6787 - 6791 (2021/05/29)
Nicotinamide adenine dinucleotide (NAD+) is a multifunctional molecule. Beyond redox metabolism, NAD+ has an equally important function as a substrate for post-translational modification enzymes, the largest family being the poly-ADP-ribose polymerases (PARPs, 17 family members in humans). The recent surprising discoveries of noncanonical NAD (NAD+/NADH)-binding proteins suggests that the NAD interactome is likely larger than previously thought; yet, broadly useful chemical tools for profiling and discovering NAD-binding proteins do not exist. Here, we describe the design, synthesis, and validation of clickable, photoaffinity labeling (PAL) probes, 2- and 6-ad-BAD, for interrogating the NAD interactome. We found that 2-ad-BAD efficiently labels PARPs in a UV-dependent manner. Chemical proteomics experiments with 2- and 6-ad-BAD identified known and unknown NAD+/NADH-binding proteins. Together, our study shows the utility of 2- and 6-ad-BAD as clickable PAL NAD probes.
Synthesis of benzamide-C-ribonucleosides by Pd-catalyzed aminocarbonylations
?tefko, Martin,Pohl, Radek,Hocek, Michal
experimental part, p. 4471 - 4483 (2009/10/17)
A novel modular, efficient and practical methodology for preparation of p- and m-substituted benzamide-C-ribonucleosides was developed. Reaction of TBS-protected 3- and 4-bromophenyl-C-ribonucleosides 1 and 4 with various primary and secondary amines or N
The synthesis and biological evaluation of benzamide riboside and its phosphordiamidates prodrugs
Zhou, Jianning,Tan, Chunyan,Zhang, Nan,Fan, Jian,Guo, Chun,Jiang, Yuyang
scheme or table, p. 787 - 790 (2009/04/06)
In order to overcome the drug resistance and enhance the membrane penetration ability of benzamide riboside [BR, (1-β-D-ribofuranosyl) benzene-3-carboxamide], which is a novel C-glycoside analogue of nicotinamide riboside and has excellent cytotoxic activity, we designed and synthesized two phosphordiamidates (1a and 1b) as prodrugs to deliver phosphorylated BR into cells. However, the bioactivity evaluation shows that 1a and 1b have lower biological activity (IC50 > 200 μM and 173 μM, respectively) compared to BR. This might be due to the fact that 1a and 1b could only serve as the BR depot form and thus could not be metabolized to the phosporylatd benzamide riboside. Copyright Taylor & Francis Group, LLC.
Efficient synthesis of benzamide riboside, a potential anticancer agent
Bonnac, Laurent F.,Gao, Guang-Yao,Chen, Liqiang,Patterson, Steven E.,Jayaram, Hiremagalur N.,Pankiewicz, Krzysztof W.
, p. 1249 - 1253 (2008/09/19)
An efficient five step synthesis of benzamide riboside (BR) amenable for a large scale synthesis has been developed. It allows for extensive pre-clinical studies of BR as a potential anticancer agent. Copyright Taylor & Francis Group, LLC.
Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogues
Krohn,Heins,Wielckens
, p. 511 - 517 (2007/10/02)
The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected
