23660-98-2

Usage

Uses

Used in Chemical Synthesis and Characterization:
Ortho-METHOXYTOPOLIN RIBOSIDE (MeoTR) is used as a reagent/reactant for the synthesis and characterization of platinum(II) oxalato complexes. These complexes are of significant interest due to their potential applications in various fields, including pharmaceuticals and materials science.
Used in Cytotoxicity Evaluation:
MeoTR is also employed in the cytotoxicity evaluation of platinum(II) oxalato complexes involving adenosine-based N-donor ligands. This application is crucial for assessing the safety and potential therapeutic effects of these complexes, as it helps to determine their impact on cell viability and overall toxicity.

Upstream product

• 6850-57-3 2-methoxybenzylamine 
• 2004-06-0 6-Chloropurine riboside 

Relevant academic research and scientific papers

N6-benzyladenosine derivatives as novel n-donor ligands of platinum(ii) dichlorido complexes

The platinum(II) complexes trans-[PtCl2(Ln)2]·xSolv 1-13 (Solv = H2O or CH3OH), involving N6-benzyladenosine-based N-donor ligands, were synthesized; Ln stands for N6-(2-methoxybenzyl)adenosine (L1, involved in complex 1), N6-(4-methoxybenzyl) adenosine (L2, 2), N6-(2-chlorobenzyl)adenosine (L3, 3), N6-(4-chlorobenzyl)- adenosine (L4, 4), N6-(2-hydroxybenzyl)adenosine (L5, 5), N6-(3-hydroxybenzyl)- adenosine (L6, 6), N6-(2-hydroxy-3-methoxybenzyl) adenosine (L7, 7), N6-(4-fluorobenzyl) adenosine (L8, 8), N6-(4-methylbenzyl) adenosine (L9, 9), 2-chloro-N6-(3-hydroxybenzyl) adenosine (L10, 10), 2-chloro-N6-(4-hydroxybenzyl)adenosine (L11, 11), 2-chloro- N6-(2-hydroxy-3- methoxybenzyl)adenosine (L12, 12) and 2-chloro-N6-(2-hydroxy-5- methylbenzyl)adenosine (L13, 13). The compounds were characterized by elemental analysis, mass spectrometry, IR and multinuclear (1H-, 13C-, 195Pt- and 15N-) and two-dimensional NMR spectroscopy, which proved the N7-coordination mode of the appropriate N6-benzyladenosine derivative and trans-geometry of the title complexes. The complexes 1-13 were found to be non-toxic in vitro against two selected human cancer cell lines (HOS and MCF7; with IC50 > 50.0 μM). However, they were found (by ESI-MS study) to be able to interact with the physiological levels of the sulfur-containing biogenic biomolecule L-methionine by a relatively simple 1:1 exchange mechanism (one Ln molecule was replaced by one L-methionine molecule), thus forming a mixed-nitrogen/sulfur-ligand dichlorido-platinum(II) coordination species.

Synthesis, biological evaluation and molecular modeling studies of N6-benzyladenosine analogues as potential anti-toxoplasma agents

Toxoplasma gondii is an opportunistic pathogen responsible for toxoplasmosis. T. gondii is a purine auxotroph incapable of de novo purine biosynthesis and depends on salvage pathways for its purine requirements. Adenosine kinase (EC.2.7.1.20) is the major enzyme in the salvage of purines in these parasites. 6-Benzylthioinosine and analogues were established as "subversive substrates" for the T. gondii, but not for the human adenosine kinase. Therefore, these compounds act as selective anti-toxoplasma agents. In the present study, a series of N6-benzyladenosine analogues were synthesized from 6-chloropurine riboside with substituted benzylamines via solution phase parallel synthesis. These N6-benzyladenosine analogues were evaluated for their binding affinity to purified T. gondii adenosine kinase. Furthermore, the anti-toxoplasma efficacy and host toxicity of these compounds were tested in cell culture. Certain substituents on the aromatic ring improved binding affinity to T. gondii adenosine kinase when compared to the unsubstituted N6-benzyladenosine. Similarly, varying the type and position of the substituents on the aromatic ring led to different degrees of potency and selectivity as anti-toxoplasma agents. Among the synthesized analogues, N6-(2,4-dimethoxybenzyl)adenosine exhibited the most favorable anti-toxoplasma activity without host toxicity. The binding mode of the synthesized N6-benzyladenosine analogues were characterized to illustrate the role of additional hydrophobic effect and van der Waals interaction within an active site of T. gondii adenosine kinase by induced fit molecular modeling.

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

SUBSTITUTION DERIVATIVES OF N6-BENZYLADENOSINE, METHODS OF THEIR PREPARATION, THEIR USE FOR PREPARATION OF DRUGS, COSMETIC PREPARATIONS AND GROWTH REGULATORS, PHARMACEUTICAL PREPARATIONS, COSMETIC PREPARATIONS AND GROWTH REGULATORS CONTAINING THESE COMPOU

The invention concerns novel substitution derivatives of N6-benzyladenosine having anticancer, mitotic, immunosuppressive and antisenescent properties for plant, animal and human cells. This invention also relates to the methods of preparation

Adenosine analogues as inhibitors of Trypanosoma brucei phosphoglycerate kinase: Elucidation of a novel binding mode for a 2-Amino-N6-substituted adenosine

As part of a project aimed at structure-based design of adenosine analogues as drugs against African trypanosomiasis, N6-, 2-amino-N6-, and N2-substituted adenosine analogues were synthesized and tested to establish structure - activity relationships for inhibiting Trypanosoma brucei glycosomal phosphoglycerate kinase (PGK), glyceraldehyde-3-phosphate dehydrogenase (GAPDH), and glycerol-3-phosphate dehydrogenase (GPDH). Evaluation of X-ray structures of parasite PGK, GAPDH, and GPDH complexed with their adenosyl-bearing substrates led us to generate a series of adenosine analogues which would target all three enzymes simultaneously. There was a modest preference by PGK for N6-substituted analogues bearing the 2-amino group. The best compound in this series, 2-amino-N6-[2-(p-hydroxyphenyl)ethyl]adenosine (46b), displayed a 23-fold improvement over adenosine with an IC50 of 130 μM. 2-[[2-(p-Hydroxyphenyl)ethyl]amino]adenosine (46c) was a weak inhibitor of T. brucei PGK with an IC50 of 500 μM. To explore the potential of an additive effect that having the N6 and N2 substitutions in one molecule might provide, the best ligands from the two series were incorporated into N6,N2-disubstituted adenosine analogues to yield N6-(2-phenylethyl)-2-[(2-phenylethyl)amino]adenosine (69) as a 30 μM inhibitor of T. brucei PGK which is 100-fold more potent than the adenosine template. In contrast, these series gave no compounds that inhibited parasitic GAPDH or GPDH more than 10-20% when tested at 1.0 mM. A 3.0 A? X-ray structure of a T. brucei PGK/46b complex revealed a binding mode in which the nucleoside analogue was flipped and the ribosyl moiety adopted a syn conformation as compared with the previously determined binding mode of ADP. Molecular docking experiments using QXP and SAS program suites reproduced this 'flipped and rotated' binding mode.