4244-45-5

Upstream product

• 128657-07-8 (S)-2-Amino-4-(6-amino-purin-9-yl)-butyric acid 
• 107-13-1 acrylonitrile 
• 66224-66-6 adenine 
• 2417-90-5 bromopropionitrile 
• 73-24-5 7H-purin-6-ylamine 

Downstream Products

• 126595-74-2 7-(2-hydroxyethyl)adenine 

Relevant academic research and scientific papers

FORMATION OF (9-ADENINYL)-ω-CYANOALKANES FROM (9-ADENINYL)-α-AMINO ACIDS

Elimination of CO2 and oxidation of the amino group of the amino acid to give the corresponding (9-adeninyl)-ω-cyanoalkanes occur under the conditions of bromination of (9-adeninyl)-α-amino acids in both alkaline and buffer solutions.

Interconnected trimeric, pentameric, and hexameric metallacycles in a singular silver-adenine framework

This Article describes the synthesis and crystallographic investigation of a silver complex of a modified adenine derivative bearing a nitrile pendant at the N9 position. All three adenine ring nitrogen atoms coordinated to silver ions, while the fourth coordination was achieved at the nitrile functionality, thus resulting in the formation of silver-mediated interconnected trimeric, pentameric, and hexameric metallacyclic rings and helical signatures in two orthogonal directions.

Customizable and Regioselective One-Pot N?H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications

DNA is one of the most exciting biomolecules in nature for developing supramolecular biofunctional nanoarchitectures owing to the highly specific and selective interactions between complementary Watson-Crick base pairing. Herein, simple and one-pot synthetic procedures have been implemented for producing a library of DNA nucleobase derivatives endowed with reactive functional groups for bioconjugation and cross-linking strategies with other (bio)molecules. Purine and pyrimidine molecules have been regioselectively N?H functionalized either via N-alkylation, N-allylation, N-propargylation or Michael-type reactions and structurally characterized. The influence of the reaction conditions was assessed and discussed. The in vitro biocompatibility of the native and nucleobase derivatives was evaluated by culturing them with human fibroblasts, revealing their cytocompatibility. The library of nucleobase derivatives holds great promise for being coupled to different biomolecules, including biopolymeric materials, lipids, and peptides, thus potentially leading to modular supramolecular nanobiomaterials for biomedicine.

Microwave-promoted Michael addition in neat water: A rapid, efficient and green method for the preparation of acyclic nucleosides

Syntheses of acyclic nucleosides were achieved in water with the aid of microwave irradiation, providing a rapid, efficient and convenient method for the preparation of acyclic nucleosides in high yields. Georg Thieme Verlag Stuttgart.

Antiviral compounds

This invention relates to purine compounds of formula (I): R1 is NH2 or OH; R2 is H or NH2; R3 is H or alkyl; each of m and n, independently, is 1, 2, 3, or 4; X is O, S, or NH; and Y is H, halogen, ORa, P(O)(ORa)2, or P(O)(ORa)(ORb), in which Ra is H, alkyl, aryl, heteroaryl, cyclyl, heterocyclyl, and Rb is wherein A is adenine, guanine, cytosine, uracil, or thymine; Rc is H or OH; Rd is H or alkyl; Re is H, alkyl, or 5-ethylidene-(3,4-dialkoxyl)-furan-2-one; provided that if R1 is NH2, R2 is H; and if R1 is OH, R2 is NH2.

Design, synthesis, and biological evaluation of novel nucleoside and nucleotide analogues as agents against DNA viruses and/or retroviruses

A novel strategy was developed for the synthesis of N7-purine acyclic nucleosides 9 and 14. The key step involved the reaction between [2-(p- methoxyphenyloxy)ethoxy]methyl chloride and N9-tritylated nucleobases 6 or 11 followed by concomitant self-detritylation. N7-Guanine acyclic nucleoside 9 exhibited antiviral activity, but was phosphorylated by both HSV and Vero cell thymidine kinases. Thus, it showed more potent cellular toxicity than acyclovir (2). N7-Adenine acyclic nucleoside 14 was found to be an excellent antiviral agent as well as a good inhibitor of calf mucosal adenosine deaminase. This inhibitory property allows for a greater expression of antiviral activity of antiviral agents, such as N9-adenine acyclic nucleoside 1 and ara-A (3). Compound 14 was phosphorylated neither by herpes simplex virus (HSV) thymidine kinase nor by Vero cell thymidine kinase, yet it enhanced the rate constant for the monophosphorylation of acyclovir (2) by HSV thymidine kinase. Consequently, the combination of acyclovir (2) and 14 exhibited greater antiviral activity than acyclovir alone. 7-[2(Phosphonomethoxy)ethyl] adenine (20) was also synthesized. The key step involved the reaction of 9-(2-cyanoethyl)adenine (15) with methyl iodoacetate in the presence of lithium 2,2,6,6-tetramethylpiperidine in THF. Unlike 9-[2- (phosphonomethoxy)ethyl] adenine (PMEA, 4), the N7-isomer 20 was not phosphorylated effectively by 5-phosphoribosyl 1-pyrophosphate synthetase (PRPP synthetase). Thus, it did not exhibit pronounced antiviral activity. Dinucleotide 5′-monophosphate 24 and its butenolide ester 25 were also synthesized. Compound 24 showed substrate activity toward PRPP synthetase and exhibited notable activity against DNA viruses. The antiviral activity of the ester derivative 25 was found to be higher than that of the parent molecule 24. Dinucleotide 5′-monophosphate 24 is suseptible to degradation by snake venom and spleen phosphodiesterases. However, its respective butenolide ester derivative 25 was completely resistant to snake venom and spleen enzymes. Butenolide ester derivatives 28 and 29 were also synthesized and exhibited notable anti-DNA virus and anti-retrovirus activity in vitro. Compounds 2, 4, 9, 14, 20, 24, 25, and 28 were also evaluated for their inhibitory effect on HSV-1-induced mortality in NMRI mice. N7-adenine acyclic nucleoside 14 [LD50 (intraperitoneal, ip) 950 mg/kg], nucleotide-containing butenolide 25 [LD50 (ip) 675 mg/kg], and butenolide 28 [LD50 (ip) 710 mg/kg] were found to be potent anti-HSV-1 agents in vivo. In addition, butenolide 28 efficiently decreased tumor formation induced by Moloney murine sarcoma virus (MSV) in NMRI mice while significantly increasing the survival time of MSV-infected mice.

CHARACTERISATION OF ADDUCTS OF NUCLEIC BASES AND ACRYLIC MONOMERS

Spectral data and thermodynamic calculations of adducts of purines (guanine, adenine), or pyrimidines (thymine, uracil) with acrylic monomers (acrylonitrile, ethyl acrylate, and ethyl crotonate) are reported.Purine adducts derive from attack at N-7 and N-9, and pyrimidine adducts derive from attack at N-1.Acrylonitrile forms also N-1, N-3 bis adducts with pyrimidines.Structural assignment was by 1H and 13C NMR and using COSY-RELAY and NOE effects.Force-field calculations indicated the most stable conformations of the reaction products.

Some Intramolecular Michael Addition of Adenine Derivatives

In our attempts to prepare polymerizable derivatives of nucleic acid bases, we investigated the reaction of adenine (1) and 9-(cyanoethyl)adenine (4) with acrylic anhydride and acryloyl chloride. reactions of adenine with methyl acrylate and vinyl acrylate were also examined.The results show that these reactions are solvent dependent and the intermediate acryloyladenine 3 can undergo a facile intramolecular Michael reaction to form 7.