4244-47-7

Usage

InChI:InChI=1/C8H9N5O2/c9-7-6-8(11-3-10-7)13(4-12-6)2-1-5(14)15/h3-4H,1-2H2,(H,14,15)(H2,9,10,11)

Upstream product

• 66224-66-6 adenine 
• 79-10-7 acrylic acid 
• 223409-15-2 9-(2-tert-butoxycarbonylethyl)adenine 
• 70259-15-3 3-(6-amino-purin-9-yl)-propionic acid methyl ester 
• 7083-40-1 3-(6-aminopurine-9-yl)-propionic acid ethyl ester 

Downstream Products

• 1092082-04-6 5-(6-aminopurin-9-yl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-pentanenitrile 
• 216597-14-7 p-nitrophenyl 3-(6-trifluoroacetoamidopurine-9-yl)propionate 
• 70138-80-6 9-(2-carboxyethyl)adenine p-nitrophenyl ester 

Relevant academic research and scientific papers

Microwave-promoted michael addition of azaheterocycles to α,β-unsaturated esters and acid under solvent-free conditions

Regioselective Michael addition of N-9 adenine to ethyl acrylate under microwave activation in solid-liquid solvent-free phase-transfer catalysis using TBAB as catalyst and DABCO as base was extended to tert-butyl acrylate and acrylic acid. Under these conditions and in the presence of a catalytic amount of KOH, first Michael addition of indole and indolylmaleimide to acrylates is also reported. Georg Thieme Verlag Stuttgart · New York.

Acidity and complex formation studies of 3-(adenine-9-yl)-propionic and 3-(thymine-1-yl)-propionic acids in ethanol-water media

The ligands 3-(adenine-9-yl)propionic acid (AA) and 3-(thymine-1-yl)propionic acid (TA) were prepared by N9-alkylation of adenine and N1-alkylation of thymine with ethylacrylate in presence of a base catalyst, followed by acid hydrolysis of the formed ethyl esters to give the corresponding propionic acid derivatives. The products were characterized by spectral methods (FTIR, 1H NMR and 13C NMR), which confirm their structures. The dissociation constants of ligands, were potentiometrically determined in 0.3 M KCl at 20-50 °C temperature range. The work was extended to study complexation behavior of AA and TA with various biologically important divalent metal ions (Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Mn2+ and Pb2+) in 50% v/v water-ethanol medium at four different temperatures, keeping ionic strength constant (0.3 M KCl). The order of the stability constants of the formed complexes decreases in the sequence Cu2+ > Pb2+ > Zn2+ > Ni2+ > Co2+ > Mn2+ > Cd2+ for both ligands. The effect of temperature was also studied and the corresponding thermodynamic functions (ΔG, ΔH, ΔS) were derived and discussed. The formation of metal complexes has been found to be spontaneous, and the stability constants were dependant markedly on the basicity of the ligands.

In Vivo X-ray Triggered Catalysis of H2 Generation for Cancer Synergistic Gas Radiotherapy

To date, hydrogen (H2) therapy has received widespread attention. However, X-ray triggered sustainable H2-producing materials with controlled release for cancer treatment have not been reported. Herein, an X-ray triggered sustainable in situ H2 producing platform, Au NR-TiO2@ZnS:Cu,Co-A(Au-TiO2@ZnS), composed of Au-amorphous TiO2 nano-dumbbell-shaped heterostructure coated with long afterglow particles, was developed for cancer synergistic H2-radiotherapy. The mechanism of H2 production was verified by theoretical calculations and in vitro experiments. Changes in the apoptosis pathway caused by the synergistic effect of H2 and radiotherapy were reported. Guided by its excellent photoacoustic imaging capabilities, mice with orthotopic liver cancer achieved excellent therapeutic effects and low inflammatory side effects, suggesting that Au-TiO2@ZnS has promising application potential for cancer treatment and prognosis.

Thermodynamic effect of complementary hydrogen bond base pairing on aromatic stacking interaction in the guanine-X-Trp complex (X = adenine, guanine, cytosine, thymine)

Four kinds of X-Trp (X = adenine, guanine, cytosine, thymine) were synthesized as model compounds to investigate the effect of complementary hydrogen bond base pairing on the stacking interaction of Trp with nucleic acid base. Association constants (K(a)) of these compounds with two guanine derivatives (9-ethylguanine and 9-ethyl-7-methylguanine) were determined by Eadie-Hofstee plots of 1H-NMR titration experiments, and the thermodynamic parameters (ΔH, ΔS and ΔG) for the respective complexes were obtained by van't Hoff analyses based on the temperature dependence of the K(a) values. The complexes were characterized by enthalpy/entropy compensations, where the interaction of cytosine-Trp with guanine derivatives was largely enthalpy- driven, accompanied by a small entropy component, whereas those of remaining complexes were all associated with a large increase in entropy, accompanied by a small positive enthalpy component. The present insight on the binding of X-Trp with a guanine base provides a thermodynamic basis for the importance of cooperative hydrogen bond pairing and aromatic stacking interactions in the specific recognition of a nucleic acid base pair by protein.

The family of N9-adenine: New entry for adenine-benzamide conjugates linked via versatile spacers

We have prepared 4-nitrobenzamide-adenine conjugates (8, 13 and 14) linked with versatile spacer such as triethylene glycol (TEG), aminocaproic acid and ethyl chains which were eventually reduced to obtain the corresponding 4-aminobenzamide-adenine conjug

The family of N9-adenine: New entry for adenine-benzamide conjugates linked via versatile spacers

We have prepared 4-nitrobenzamide-adenine conjugates (8, 13 and 14) linked with versatile spacer such as triethylene glycol (TEG), aminocaproic acid and ethyl chains which were eventually reduced to obtain the corresponding 4-aminobenzamide-adenine conjug

Pleuromutilin derivatives having a purine ring. Part 1: New compounds with promising antibacterial activity against resistant Gram-positive pathogens

In the course of our research aimed at the discovery of metabolic stable pleuromutilin derivatives with more potent antibacterial activity against Gram-positive pathogens than previous analogues, a series of compounds bearing a purine ring were prepared and evaluated. From SAR studies, we identified two promising compounds 85 and 87, which have excellent in vitro activity against a number of Gram-positive pathogens, including existing drug-resistant strains, and potent in vivo efficacy.

Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers

DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respecti

Oligopyrrole carboxamides linked with a nucleobase as potential DNA minor groove binding ligands: Synthesis, DNA binding and biological evaluation

The synthesis of a series of new oligopyrrole carboxamides closely related to netropsin and distamycin A, linked with a nucleobase is reported. The new compounds possess similar structure elements as the known peptide nucleic acids which are interesting s

Reversible inhibitors of S-adenosyl-L-homocysteine hydrolase and uses thereof

The present invention provides compositions and methods for reversibly inhibiting S-adenosyl-L-homocysteine (SAH) hydrolase. The compounds of the present invention can be used in combination with an anti-hemorrhagic viral infection agent, an immunosuppressant, a homocysteine lowering agent, or an anti-neoplasm agent. The compositions and methods of the present invention can be used for the prevention and treatment of hemorrhagic virus infection, autoimmune diseases, autograft rejection, neoplasm, hyperhomocysteineuria, cardiovascular disease, stroke, Alzheimer's disease, or diabetes.