115693-37-3

Upstream product

• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 593-56-6 N-methoxylamine hydrochloride 
• 87-42-3 6-chloropurine 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 67-62-9 O-Methylhydroxylamin 
• 64-18-6 formic acid 
• 110526-60-8 5-Amino-1-benzyl-N'-methoxy-1H-imidazole-4-carboxamidine 
• 10184-56-2 9-Benzyl-1-methoxy-1,9-dihydro-purin-6-ylideneamine; hydriodide 

Downstream Products

• 1616366-68-7 C₂₀H₂₀N₅O⁽¹⁺⁾*Br^(1-) 

Relevant academic research and scientific papers

Crystallographic signatures of N6-methoxyadenine imino tautomer-silver complexes

Detailed crystallographic analysis of four silver complexes of N9-benzyl-N6-methoxyadenine, 1, on the basis of three different counteranions and silver ion stoichiometry, is discussed in this article. 1 is a rare tautomer of adenine, which exhibits promutagenic behavior as it partly mimics hydrogen bond donor and acceptor properties of guanine and mispairs with cytosine. Complexes 2 and 4 exhibit discrete Ag2L2 dimer, while complex 3 shows two AgL2 units in addition to a Ag 2L2 dimer, all in a head-to tail fashion. Complex 5, on the other hand, shows four AgL2 units coordinated in a head-to-head fashion affording a three-dimensional lattice stabilized by CH??? F interactions. Various noncovalent interactions such as hydrogen bonding, CH-π interactions, argentophilic interactions, and Ag-π interactions stabilize these complexes.

Antimicrobial and cytotoxic activity of agelasine and agelasimine analogs

Agelasine and agelasimine derivatives with substantially less complicated terpenoid side chains compared to the naturally occurring compounds have been synthesized and their ability to inhibit growth of microorganisms and cancer cells has been studied. Co

Targeting cytotoxicity and tubulin polymerization by metal-carbene complexes on a purine tautomer platform

This communication describes the synthesis, structural investigation and tubulin binding of purine rare imino-tautomer based Ag(i) and Hg(ii)-carbene complexes. These complexes exhibit cytotoxicity through tubulin interaction by binding to a site close to

Design, synthesis and structure-activity relationships of a series of 9-substituted adenine derivatives as selective phosphodiesterase type-4 inhibitors

Adenine derivatives substituted in position 9 have been demonstrated to have potent cyclic nucleotide phosphodiesterase (PDE) inhibition properties with high selectivity toward PDE-4. Starting from our initial lead compound 9-(2-fluorobenzyl)-N6-methyl-2-trifluoromethyladenine (4, NCS613), we designed and synthesized a new series of 9-substituted derivatives for developing structure-activity relationship studies. This new series of derivatives showed increased potencies and better selectivity profiles. Structural modifications were achieved in parallel on three different positions of the adenine ring, and led to the following observations: (i) introduction of a lipophilic substituent such as trifluoromethyl, n-propyl group or iodine in the C-2 position is favourable for both the PDE-4 inhibitory activity and the selectivity towards other isoenzymes; (ii) functionalization of the N9 benzyl group with a 2-methoxy substituent led to remarkably more active compounds; (iii) replacement of the N6-methylamino moiety by other amino groups is detrimental to the activity. Among all derivatives prepared, the 9-(2-methoxybenzyl)-N6-methyl-2-trifluoromethyladenine (9r), 9-(2-methoxybenzyl)-N6-methyl-2-n-propyladenine (9s), and the 2-iodo-9-(2-methoxybenzyl)-N6-methyladenine (13b) were found to be the most potent inhibitors within this series (PDE-4-IC50=1.4, 7.0, and 0.096 nM, respectively). Compared to our reference compound 4, which showed an IC50 of 42 nM, the derivative 13b was found 450-fold more potent. Moreover, 2-iodo-9-(2-methoxybenzyl)-N6-methyladenine (13b) and 9-(2-methoxybenzyl)-N6-methyl-2-trifluoromethyladenine (9r), were at least 50 000-150 000 times more selective for the PDE-4 than for the other PDE families. Additionally, these new derivatives showed improved efficiency in inhibiting the TNFα release from mononuclear cells from healthy subjects (e.g. adenines 7l, 9s and 13b). Thus, compounds 7l, 9r, 9s and 13b are among the most potent and selective PDE-4 inhibitors reported so far and represent very promising pharmacological tools for a better understanding of the signal transduction involving cyclic AMP within the cell: this pathway is implicated in the physiology and the pathophysiology of inflammation, asthma and autoimmune disorders.