25477-96-7

Usage

Uses

Used in Biochemical Research:
ETHYL ADENINE-9-ACETATE is used as a substrate for various enzymes in biochemical research, facilitating the study of enzyme mechanisms and the development of new biochemical assays.
Used in Pharmaceutical Synthesis:
As a precursor in the synthesis of pharmaceuticals, ETHYL ADENINE-9-ACETATE contributes to the creation of novel drug candidates, potentially leading to the development of new treatments for various diseases.
Used in Antiviral Research:
ETHYL ADENINE-9-ACETATE is being investigated for its potential antiviral properties, with the aim of identifying its effectiveness against specific viral infections and possibly contributing to the development of antiviral medications.
Used in Antitumor Research:
ETHYL ADENINE-9-ACETATE is also under investigation for its potential antitumor properties, exploring its capacity to inhibit tumor growth and its possible use in cancer therapy.
Used in Drug Development:
Due to its unique structure and potential biological activities, ETHYL ADENINE-9-ACETATE is utilized in drug development processes, where it may lead to the discovery of new therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C9H11N5O2/c1-2-16-6(15)3-14-5-13-7-8(10)11-4-12-9(7)14/h4-5H,2-3H2,1H3,(H2,10,11,12)

Upstream product

• 35910-49-7 methyl 5-(6-amino-purin-9-yl)-O²,O³-isopropylidene-D-5-deoxy-ribofuranoside 
• 64-17-5 ethanol 
• 105-36-2 ethyl bromoacetate 
• 66224-66-6 adenine 
• 133469-38-2 (5-Amino-4-cyano-imidazol-1-yl)-acetic acid ethyl ester 
• 122-51-0 orthoformic acid triethyl ester 
• 40428-86-2 sodium adeninate 
• 105-39-5 chloroacetic acid ethyl ester 
• 73-24-5 7H-purin-6-ylamine 

Downstream Products

• 149376-66-9 ethyl (N⁶-(benzyloxycarbonyl)adenin-9-yl)acetate 
• 55175-33-2 Ethyl ester of hypoxanthinyl-9-acetic acid 
• 171406-46-5 6-N-(benzoyl)-9-(ethoxycarbonylmethyl)adenine 
• 6298-53-9 9-carboxymethylhypoxanthine 
• 149376-67-0 [6-N-(benzyloxycarbonyl)-adenin-9-yl]-acetic acid 
• 149376-69-2 N-((N⁶-(benzyloxycarbonyl)adenin-9-yl)acetyl)-N-(2-Boc-aminoethyl)glycine 
• 149376-68-1 ethyl N-((N⁶-(benzyloxycarbonyl)adenin-9-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate 
• 186046-99-1 (N⁶-Boc-N⁹-adeninyl)acetic acid 
• 263254-51-9 ([2-(9H-Fluoren-9-ylmethoxycarbonylamino)ethyl]-{2-[6-(4-methoxybenzoylamino)purin-9-yl]acetyl}amino)acetic acid tert-butyl ester 
• 172405-18-4 N⁹-(carboxymethyl)-N⁶-(4-methoxybenzoyl)adenine 
• 682753-01-1 N-{2-[N'⁶-(4-methoxytrityl)-adenin-9-yl]-acetyl}-N-{2-[1-(4,4-dimethyl-2,6-dioxo-cyclohexyliden)ethylamino]ethyl}glycine 
• 864776-34-1 methyl N-{2-[N'⁶-(4-methoxytrityl)-adenin-9-yl]-acetyl}-N-{2-[1-(4,4-dimethyl-2,6-dioxo-cyclohexyliden)ethylamino]ethyl}glycinate 
• 172405-51-5 [N⁶-(4-methoxytrityl)-adenin-9-yl]-acetic acid 
• 175695-25-7 ethyl [N⁶,N⁶-bis(tert-butoxycarbonyl)adenin-9-yl]acetic acid 

Relevant academic research and scientific papers

Thermal-induced dynamic self-assembly of adenine-grafted polyoxometalate complexes

A new kind of organic-inorganic hybrid complexes based on polyoxometalate were synthesized through symmetrically grafting two adeninyl groups onto Anderson-type MnMo6 clusters and encapsulating the clusters by organic surfactants. The resultant complexes exhibited thermal-induced dynamic self-assembly behaviors which greatly depended on the ambient temperature and the chain length of cationic surfactants. With the encapsulation of a short surfactant tetrabutyl ammonium, the complex assembled into fibrous, rod-like, and tubular architectures respectively upon heating; while for the case of using a long surfactant dimethyldioctadecyl ammonium as counter ions, the assemblies of the complex transformed from fibers to spheres with the increased temperature. Moreover, the two types of transformations were both reversible during a cooling process. The related mechanism was investigated by combining multiple characterization methods including X-ray crystallography, XPS, FT-IR and temperature-dependent 1H NMR, which indicated that such a thermal-induced morphological transformation resulted from a synergy effect of the variation of the multiple hydrogen bonds among the complexes and the rearrangement of the surfactants surrounding the MnMo6 clusters. These results demonstrated a new concept that hydrogen bonds can be rationally employed as the driving force for the fabrication of polyoxometalate-based materials with smart responsive properties.

Synthesis and intramolecular cyclisation of 5-aminoimidazolealkanoates and their conversion to purine derivatives

Synthesis of ethyl (9-hypoxanthinyl)- and (9-adeninyl)acetates, ethyl 3-(9-hypoxanthinyl)- and 3-(9-adeninyl)propanoates, and ethyl 2-(9-hypoxanthinyl)- and 2-(9-adeninyl)propanoates from appropriately substituted 5-aminoimidazole precursors is described. Cyclisation of the imidazoles also resulted in formation of an imidazopyrimidine and novel imidazoimidazoles.

Synthesis and biological evaluation of new HIV-1 protease inhibitors with purine bases as P2-ligands

Introducing purine bases to P2-ligands might enhance the potency of Human Immunodeficiency Virus-1 (HIV-1) protease inhibitory because of the carbonyl and NH groups promoting the formation of extensive H-bonding interactions. In this work, thirty-three compounds are synthesized and evaluated, among which inhibitors 16a, 16f and 16j containing N-2-(6-substituted-9H-purin-9-yl)acetamide as the P2-ligands along with 4-methoxylphenylsulfonamide as the P2′-ligand, display potent inhibitory effect on the activity of HIV-1 protease with IC50 43 nM, 42 nM and 68 nM in vitro, respectively.

Lead optimization and biological evaluation of fragment-based cN-II inhibitors

The development of cytosolic 5′-nucleotidase II (cN-II) inhibitors is essential to validate cN-II as a potential target for the reversion of resistance to cytotoxic nucleoside analogues. We previously reported a fragment-based approach combined with molecular modelling, herein, the selected hit-fragments were used again in another computational approach based on the Ilib-diverse (a software enabling to build virtual molecule libraries through fragment based de novo design) program to generate a focused library of potential inhibitors. A molecular scaffold related to a previously identified compound was selected and led to a novel series of compounds. Ten out of nineteen derivatives showed 50–75% inhibition on the purified recombinant protein at 200 μM and among them three derivatives (12, 13 and 18) exhibited Ki in the sub-millimolar range (0.84, 2.4 and 0.58 mM, respectively). Despite their only modest potency, the cN-II inhibitors showed synergistic effects when used in combination with cytotoxic purine nucleoside analogues on cancer cells. Therefore, these derivatives represent a family of non-nucleos(t)idic cN-II inhibitors with potential usefulness to overcome cancer drug resistance especially in hematological malignancies in which cN-II activity has been described as an important parameter.

Simple and efficient synthesis of novel glycosyl thiourea derivatives as potential antitumor agents

The practical synthesis of pseudonucleosides incorporating thiourea derivative by coupling of monosaccharides (d-galactose, d-glucose and d-xylose) per-O-acetylated glycosyl isothiocyanates and different heterocyclic hydrazide derivatives is reported. The method involves the preparation of per-O-acetylated glycosyl isothiocyanates from per-O-acetylated sugars (two-step synthesis), which couple with heterocyclic hydrazides from amines to give thiourea-linked pseudonucleosides. All newly synthesized pseudonucleosides were assayed against human lung cancer-cell lines (PG) and human liver cancer-cell lines (BEL-7402) in vitro. The 2-(4-methoxybenzamide)-benzoimidazole-1-yl-acetyl pseudonucleosides showed moderate inhibition against these two cancer-cell lines with EC50 from 22.8 to 76.4 μM and from 54.9 to 82.4 μM, respectively. And the other compounds did not demonstrate any significant cytotoxicity even at concentrations up to 200 μM.

Diversity-oriented chemical modification of heparin: Identification of charge-reduced N-acyl heparin derivatives having increased selectivity for heparin-binding proteins

The diversity-oriented chemical modification of heparin is shown to afford charge-reduced heparin derivatives that possess increased selectivity for binding heparin-binding proteins. Variable N-desulfonation of heparin was employed to afford heparin fract

Dde-protected PNA monomers, orthogonal to Fmoc, for the synthesis of PNA-peptide conjugates

Peptide nucleic acids have become, arguably, one of the most interesting of DNA mimics. Herein the efficient solution phase synthesis of four novel 1-(4,4-dimethyl-2,6-dioxacyclohexylidene)ethyl/4-methoxytrityl (Dde/Mmt) protected PNA monomers is reported

Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility

A novel class of compounds known as peptide nucleic acids, bind complementary DNA and RNA strands, and generally do so more strongly than the corresponding DNA or RNA strands while exhibiting increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases, including 2,6-diaminopurine, attached to a polyamide backbone, and contain alkyl amine side chains.

Synthetic procedures for peptide nucleic acids

A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

Peptide nucleic acids having 2,6-diaminopurine nucleobases

A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and binding affinity. The peptide nucleic acids of the invention comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone. Some PNAs of the invention also contain C1-C8alkylamine side chains.