23666-24-2

Basic information

• Product Name: para-TOPOLIN RIBOSIDE(pTR)
• Synonyms: para-TOPOLIN RIBOSIDE(pTR);N-(4-Methoxybenzyl)-adenosine;N6-(4-Methoxybenzyl)adenosine;N6-(p-Methoxybenzyl)adenosine
• CAS NO: 23666-24-2
• Molecular Formula: C₁₈H₂₁N₅O₅
• Molecular Weight: 387.38984
• Mol File: 23666-24-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 154-156℃
• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: para-TOPOLIN RIBOSIDE(pTR)(CAS DataBase Reference)
• NIST Chemistry Reference: para-TOPOLIN RIBOSIDE(pTR)(23666-24-2)
• EPA Substance Registry System: para-TOPOLIN RIBOSIDE(pTR)(23666-24-2)

Safety Data

• Hazardous Substances Data: 23666-24-2(Hazardous Substances Data)

Usage

Description

para-TOPOLIN RIBOSIDE(pTR) is a chemical compound that has potential applications in various fields, particularly in the synthesis of platinum complexes with hydroxy-, methoxy-, fluoro-, and chloro-substituted N-benzyladenosine ligands. These complexes are being investigated for their anti-tumor properties.

Uses

Used in Pharmaceutical Industry:
para-TOPOLIN RIBOSIDE(pTR) is used as a reagent/reactant for the synthetic preparation of platinum complexes with hydroxy-, methoxy-, fluoro-, and chloro-substituted N-benzyladenosine ligands. These complexes are being developed as potential anti-tumor agents, aiming to provide new treatment options for cancer patients.
Used in Research and Development:
In the field of research and development, para-TOPOLIN RIBOSIDE(pTR) is utilized for the synthesis and evaluation of cytotoxicity of platinum complexes. This helps scientists and researchers to understand the effectiveness of these complexes in combating tumor growth and to further optimize their properties for better therapeutic outcomes.

Upstream product

• 2393-23-9 4-methoxy-benzylamine 
• 58-63-9 Inosine 
• 2004-06-0 6-Chloropurine riboside 

Downstream Products

• 58-61-7 adenosine 
• 1325711-80-5 C₂₁H₂₄ClN₅O₄ 
• 1325711-79-2 C₂₈H₃₁N₅O₇S 
• 1325711-66-7 C₁₈H₂₀ClN₅O₄ 
• 1325711-81-6 5'-azido-5'-deoxy-2',3'-O-isopropylidene-N₆-(4-methoxybenzyl)adenosine 
• 1325711-67-8 C₁₈H₂₀N₈O₄ 
• 1362021-71-3 C₂₁H₂₆N₆O₄ 
• 1325711-82-7 C₂₃H₂₈N₆O₅ 
• 1325711-68-9 5'-acetamido-5'-deoxy-N₆-(4-methoxybenzyl)adenosine 
• 1325711-83-8 C₂₈H₃₂N₆O₆S 
• 1325711-69-0 C₂₅H₂₈N₆O₆S 
• 1325711-78-1 C₂₁H₂₅N₅O₅ 

Relevant articles and documents

NMR for screening and a biochemical assay: Identification of new FPPS inhibitors exerting anticancer activity

Farnesyl pyrophosphate synthase (FPPS) is a crucial enzyme for the synthesis of isoprenoids and the key target of nitrogen-containing bisphosphonates (N-BPs). N-BPs are potent and selective FPPS inhibitors that are used in the treatment of bone-related diseases, but have poor pharmacokinetic properties. Given the key role played by FPPS in many cancer-related pathways and the pharmacokinetic limits of N-BPs, hundreds of molecules have been screened to identify new FPPS inhibitors characterized by improved drug-like properties that are useful for broader therapeutic applications in solid, non-skeletal tumours. We have previously shown that N6-isopentenyladenosine (i6A) and its related compound N6-benzyladenosine (2) exert anti-glioma activity by interfering with the mevalonate pathway and inhibiting FPPS. Here, we report the design and synthesis of a panel of N6-benzyladenosine derivatives (compounds 2a-m) incorporating different chemical moieties on the benzyl ring. Compounds 2a-m show in vitro antiproliferative activity in U87MG glioma cells and, analogous to the bisphosphonate FPPS inhibitors, exhibit immunogenic properties in ex vivo γδ T cells from stimulated peripheral blood mononuclear cells (PBMCs). Using saturation transfer difference (STD) and quantitative 1H nuclear magnetic resonance (NMR) experiments, we found that 2f, the N6-benzyladenosine analogue that includes a tertbutyl moiety in the para position of the benzyl ring, is endowed with increased FPPS binding and inhibition compared to the parent compounds i6A and 2. N6-benzyladenosine derivatives, characterized by structural features that are significantly different from those of N-BPs, have been confirmed to be promising chemical scaffolds for the development of non N-BP FPPS inhibitors, exerting combined cytotoxic and immunostimulatory activities.

Design and Synthesis of Novel Dual-Action Compounds Targeting the Adenosine A2A Receptor and Adenosine Transporter for Neuroprotection

A novel compound, N6-(4-hydroxybenzyl)adenosine, isolated from Gastrodia elata and which has been shown to be a potential therapeutic agent for preventing and treating neurodegenerative disease, was found to target both the adenosine A2A/

Preparation, biological activity and endogenous occurrence of N6-benzyladenosines

Cytokinin activity of forty-eight 6-benzyladenosine derivatives at both the receptor and cellular levels as well as their anticancer properties were compared in various in vitro assays. The compounds were prepared by the condensation of 6-chloropurine rib