104715-57-3

Usage

InChI:InChI=1/C9H11N5O/c10-8-7-9(12-5-11-8)14(6-13-7)3-1-2-4-15/h1-2,5-6,15H,3-4H2,(H2,10,11,12)/b2-1+

Upstream product

• 104715-56-2 9-(trans-4-chloro-2-buten-1-yl)adenine 
• 114978-79-9 4-(6-Amino-purin-9-yl)-but-2-yn-1-ol 
• 66224-66-6 adenine 
• 114978-78-8 9-<1-(benzoyloxy)but-2-yn-1-yl>adenine 

Relevant academic research and scientific papers

Synthesis and Biological Properties of 9-(trans-4-Hydroxy-2-buten-1-yl)adenine and Guanine: Open-Chain Analogues of Neoplanocin A

Alkylation of adenine (5a) or 2-amino-6-chloropurine (5b) with excess trans-1,4-dichloro-2-butene (4), effected by K2CO3 in dimethyl sulfoxide or tetra-n-butylammonium fluoride in tetrahydrofuran, led 90-95percent regioselectivity to 9-alkylpurines 6a and 6b.The title compounds 2a and 2b were obtained by refluxing intermediates 6a and 6b in 0.1 M NaOH or HCl.Adenine derivative 2a is a substrate for adenosine deaminase whereas both 2a and 2b exhibit 50percent inhibition of growth of murine leukemia L 1210 cell culture at 1 mM concentration.

Novel open-chain nucleotides imitating 2',3'-dideoxy-2',3'- didehydronucleotides: Synthesis and substrate properties toward DNA polymerases

A new series of acyclic nucleotide diphosphates was synthesized and evaluated as potential inbibitors of HIV reverse transcriptases.

Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase

A series of 9-(hydroxyalkenyl)purines (adenines and 3-deazaadenines), which are analogues of neplanocin A, were synthesized. The analogues were tested as inhibitors of bovine liver and murine L929 cell S-adenosylhomocysteine (AdoHcy) hydrolase (EC 3.3.1.1) and as inhibitors of vaccinia virus replication in murine L929 cells. Compounds 1b, 2a, 2b, 4a, 4b, 7, 9a, and 9b showed the best inhibitory effects toward bovine liver AdoHcy hydrolase, with compound 4b being the most potent. The compounds that were shown to be the most potent inhibitors of the bovine liver AdoHcy hydrolase all contained an allylic hydroxyl group in the cis position to the adenine or the 3-deazaadenine rings. It was concluded that the cis arrangement of the allylic hydroxyl groups in these acyclic compounds represented the minimum structural requirement of the trihydroxycyclopentenyl ring of neplanocin A to show inhibitory effects against AdoHcy hydrolase. The antiviral effects of these acyclic analogues were significantly less than neplanocin A; however, there appears to be a correlation between the antiviral activity and the inhibition of AdoHcy hydrolase for compounds 2a, 2b, 4a, 4b, and 7. Analogue 4b, which exhibited the best antiviral activity (IC50=70 μM) in this acyclic series, is substantially less potent than neplanocin A (IC50=0.08 μM) as an antiviral agent.