6811-77-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Deazaadenine is used as a research compound for studying the structure and function of nucleic acids. Its unique chemical properties allow scientists to investigate the role of adenine in various biological processes and develop a better understanding of its interactions with other molecules.
Used in Drug Development:
3-Deazaadenine is used as a lead compound in the development of new drugs targeting various diseases. Its modified structure may offer unique biological activities and improved pharmacokinetic properties compared to natural adenine, making it a valuable tool in the design of novel therapeutic agents.
Used in Nucleic Acid-Based Therapies:
3-Deazaadenine is used as a component in the development of nucleic acid-based therapies, such as antisense oligonucleotides and RNA interference (RNAi). Its ability to form hydrogen bonds and participate in base pairing, along with its altered chemical reactivity, may enhance the stability and efficacy of these therapeutic agents.

InChI:InChI=1/C6H6N4/c7-6-5-4(1-2-8-6)9-3-10-5/h1-3H,(H2,7,8)(H,9,10)

Upstream product

• 149299-08-1 4-chloro-1⁽³⁾H-imidazo[4,5-c]pyridine; hydrochloride 
• 130948-34-4 4-Amino-1-(2,3-dideoxy-β-D-glyceropentofuranosyl)-1H-imidazo<4,5-c>pyridine 
• 78582-17-9 4-Amino-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-imidazo<4,5-c>pyridine 
• 98858-05-0 4-azidoimidazo[4,5-c]pyridine 
• 52559-17-8 2-chloro-3-deazaadenine 
• 2587-02-2 2,6-dichloro-[4]pyridylamine 
• 109-09-1 2-chloropyridine 
• 2402-95-1 2-chloropyridine-N-oxide 
• 14432-16-7 2-chloro-4-nitropyridine-N-oxide 
• 14432-12-3 4-Amino-2-chloropyridine 
• 2789-25-5 2-chloro-3-nitropyridin-4-amine 
• 161263-95-2 2-(morpholin-4-yl)-pyridine-3,4-diamine 
• 272-97-9 Imidazo<4,5-c>pyridin 
• 91184-02-0 1H-Imidazo[4,5-c]pyridine-N-oxide 

Downstream Products

• 78582-17-9 4-Amino-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-imidazo<4,5-c>pyridine 
• 668268-64-2 8-chloro-3-deazaadenine 
• 668268-69-7 3-chloro-3-deazaadenine 
• 52559-17-8 2-chloro-3-deazaadenine 
• 881844-12-8 4-(isobutyrylamino)-1H-imidazo[4,5-c]pyridine 
• 881844-13-9 4-amino-1-[2'-deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-7-nitro-1H-imidazo[4,5-c]pyridine 
• 881844-18-4 4-amino-3-[2'-deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-7-nitro-3H-imidazo[4,5-c]pyridine 
• 137427-72-6 cyclic ester of 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)-3-deazaadenine 
• 1266379-69-4 1-[5-O-(4,4-dimethoxytrityl)-2-deoxy-β-D-erythro-pentofuranosyl]-4-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-1H-imidazo[4,5-c]pyridine 
• 1266379-70-7 C₄₉H₅₉N₆O₈P 
• 1266379-67-2 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-1H-imidazo[4,5-c]pyridine 
• 112318-10-2 9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl)-3-deazaadenine 
• 934816-44-1 4-(N₆,N₆-di-tert-butyloxycarbonylamino)-imidazo[4,5-c]pyridine 
• 1449481-47-3 C₁₆H₁₂N₄O 

Relevant academic research and scientific papers

Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis

Access to 3-deazaadenosine (c3A) building blocks for RNA solid-phase synthesis represents a severe bottleneck in modern RNA research, in particular for atomic mutagenesis experiments to explore mechanistic aspects of ribozyme catalysis. Here, w

Impact of 3-deazapurine nucleobases on RNA properties

Deazapurine nucleosides such as 3-deazaadenosine (c3A) are crucial for atomic mutagenesis studies of functional RNAs. They were the key for our current mechanistic understanding of ribosomal peptide bond formation and of phosphodiester cleavage in recentl

MLL1 INHIBITORS AND ANTI-CANCER AGENTS

The present invention provides a compound of Formula (I): or an enantiomer, an enantiomeric mixture, or a pharmaceutically acceptable salt thereof; wherein the variables are as defined herein. The present invention further provides pharmaceutical composit

Pharmaceutical composition for treating hyperplasia of mammary glands as well as preparation method and application of pharmaceutical composition

The invention belongs to the technical field of medicine and particularly relates to a pharmaceutical composition for treating hyperplasia of mammary glands. The pharmaceutical composition has the structure in a formula shown in the description. The invention also relates to a preparation method and an application of the pharmaceutical composition for treating hyperplasia of mammary glands. The medicine can relieve mammary tissue hyperplasia lesion, has significant treatment effects on patients suffering from hyperplasia of mammary glands and is stable in curative effect, high in cure rate andlow in recurrence rate.

Synthesis, conformational study and antiviral activity of L-like neplanocin derivatives

The L-like enantiomer of 9-(trans-2′, trans-3′-dihydroxycyclopent-4′-enyl)-3-deazaadenine (DHCDA) (1), its 3-deaza-3-bromo derivative (3), and the conformational restricted methanocarba (MC) nucleoside analogues (2 and 4) were synthesized. X-ray crystal structures showed the L isomer MC analogue 4 adopts a similar North-like locked conformation as conventional D-MC nucleosides, while the DHCDA analogue 3 preferred south-like conformer. Compounds 1 and 4 showed potent antiviral activity against norovirus, while compound 2 and 3 were less potent or inactive. The conformational behavior of “sugar” puckering (north/south) and nucleobase orientation (syn /anti) may contribute to the antiviral activity differences. For compound 3, antiviral activity was also found against Ebola virus.

Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter

In the course of our study on fungal purine transporters, a number of new 3-deazapurine analogues have been rationally designed, based on the interaction of purine substrates with the Aspergillus nidulans FcyB carrier, and synthesized following an effective synthetic procedure. Certain derivatives have been found to specifically inhibit FcyB-mediated [3H]-adenine uptake. Molecular simulations have been performed, suggesting that all active compounds interact with FcyB through the formation of hydrogen bonds with Asn163, while the insertion of hydrophobic fragments at position 9 and N6 of 3-deazaadenine enhanced the inhibition.

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.

CYCLOPENTENOL NUCLEOSIDE COMPOUNDS, INTERMEDIATES FOR THEIR SYNTHESIS AND METHODS OF TREATING VIRAL INFECTIONS

The present invention relates to compounds according to the structure (I), Where B is formula (Ia), formula (Ib) or formula (Ic); A is H, OR2 or halogen (F, Cl, Br, I, preferably F or Br, more preferably F); A' is H, OR2 or halogen (F, Cl, Br, I, preferably F or Br, more preferably F); A" is H or OR1, with the proviso that when A' is OR , A is H; and when A is OR2 , A' is H; X is C-R3 or N; Y is C-R3 or N; preferably X or Y is N and X and Y are not both simultaneously N; R3 is H or C1-C3 alkyl; D is H or NHR2; E is absent or H; G is O or NHR2; J is N or C-R4; K is N or C-H; R4 is H, halogen (F, Cl, Br, I), CN, -C(=O)NH2, NH2, NO2, -C=C-H (cis or trans) or -C≡C-H; Ra is H or CH3; Each R1 is independently H, an acyl group, a C1 - C20 alkyl or ether group, a phosphate, diphosphate, triphosphate, phosphodiester group; Each R2 is independently H, an acyl group, a C1 - C20 alkyl or ether group; and Pharmaceutically acceptable salts, solvates or polymorphs thereof.

Synthesis of 3-deaza-3-nitro-2′-deoxyadenosine

Photoactivable deoxyadenosine mimic, 3-deaza-3-nitro-2′- deoxyadenosine (2), was prepared using two different synthetic routes. The first route involved base catalyzed glycosylation of 3-deaza-3-nitroadenine, which was prepared by regioselective nitration

Design and Synthesis of a Series of Chlorinated 3-Deazaadenine Analogues

A series of chlorinated adenine analogues were designed with sights set on the development of potential antitumor agents. During the synthetic efforts, two unexpected compounds were identified. Their synthesis, along with synthesis of the chlorinated targets is presented herein.