1928-89-8

Upstream product

• 123-75-1 pyrrolidine 
• 87-42-3 6-chloropurine 
• 68-94-0 hypoxanthine 
• 87-42-3 6-chloro-7H-purine 
• 50-66-8 6-methylthiopurine 
• 81693-59-6 5-amino-4-(cyanoformimidoyl)-1H-imidazole 
• 19769-32-5 6-methylsulfonylpurine 

Relevant academic research and scientific papers

Design, synthesis and ability of non-gold complexed substituted purine derivatives to inhibit LPS-induced inflammatory response

In order to study the anti-inflammatory activity of novel 6-substituted and 6,9-disubstituted purine derivatives, 20 compounds, L1–10 and W1–10, derived from purine and lacking a gold complex were designed, synthesized and their anti-inflammatory activity was screened. LPS-induced TNF-α, IL-1β, IL-6, PGE2, NO, COX-2 and iNOS mRNA were evaluated, and western blot and NF-κB p65 translocation assay were performed in RAW 264.7 macrophages. Furthermore, carrageenan-induced hind paw edema experiments were performed in mice. Compound L1, L4, W2, and W4 markedly exerted a dose-dependent inhibition of TNF-α, IL-1β, IL-6 and PGE2 release induced by LPS in RAW 264.7 macrophages. Moreover, these compounds strongly inhibited LPS-induced NO, COX-2 and iNOS mRNA in the same cells. Anti-inflammatory activity tests in vivo showed that L1 and L4 were more effective than Au(L3)(PPh3), a known anti-inflammatory agent, at 2–5 h, and W4 was the most effective at 3–5 h after dosing. Thus, W2, W4, and L1, L4, could effectively inhibit LPS-induced inflammatory response in vitro and in vivo suggesting a promising role as anti-inflammatory agents.

Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System

Buchwald-Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to be reported. A wide variety of chloroheteroarenes could be coupled efficiently with primary and secondary amines as well as selected amino acid esters under mild reaction conditions. Catalytic efficiency of the developed protocol also promotes late-stage functionalization of active pharmaceutical ingredients (APIs) such as antibiotics (floxacins) and anticancer drugs. The catalytic system also performs efficiently at a very low concentration of 0.0001 mol % (TON = 980,000) and can be recycled 12 times without any appreciable loss in activity. Theoretical calculations reveal that the π-acceptor ability of the ligand PTABS is the main reason for the appreciably high reactivity of the catalytic system. Preliminary characterization of the catalytic species in the reaction was carried out using UV-VIS and ESR spectroscopy, providing evidence for the Cu(II) oxidation state.

Reactions of Adenine and Its N-Exo Substituted Analogues with Phenyl Glycidyl Ether

Abstract: The features of reactions of adenine with phenyl glycidyl ether depending on the solvent nature were studied. In DMF in the presence of K2CO3, an N9-alkyl derivative, an experimental antiviral drug 9-(2-hydroxy-3-phenoxypropyl)adenine, was formed predominantly. During alkylation in acetic acid, besides N9-, N3-, and N7-alkylation products were also isolated. Alkylation of 6-[alkyl(dialkyl)amino]purines with phenyl glycidyl ether in DMF produced N-exo substituted 9-(2-hydroxy-3-phenoxypropyl)adenine analogues.

Purine and purine isostere derivatives of ferrocene: An evaluation of ADME, antitumor and electrochemical properties

Novel purine and purine isosteres containing a ferrocene motif and 4,1-disubstituted (11a?11c, 12a?12c, 13a?13c, 14a?14c, 15a?15c, 16a, 23a?23c, 24a?24c, 25a?25c) and 1,4-disubstituted (34a?34c and 35a?35c) 1,2,3-triazole rings were synthesized. The most

HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines

A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

Novel purine benzimidazoles as antimicrobial agents by regulating ROS generation and targeting clinically resistant Staphylococcus aureus DNA groove

A novel series of purine benzimidazole hybrids were designed and synthesized for the first time with the aim to circumvent the increasing antibiotic resistance. Hexyl appended hybrid 3c gave potent activities against most of the tested bacteria and fungi especially against multidrug-resistant strains Staphylococcus aureus (MIC = 4 μg/mL). Structure-activity relationships revealed that the benzimidazole fragment at the 9-position of purine played an important role in exerting potentially antibacterial activity. Both cell toxicity and ROS generation assays indicated that the purine derivative 3c showed low cytotoxicity and could be used as a safe agent. Molecular modeling suggested that hybrid 3c could bind with the residues of Topo IA through hydrogen bonds and electrostatic interactions. Quantum chemical studies were also performed on the target compound 3c to understand the structural features essential for activity. The active molecule 3c could effectively interact with S. aureus DNA to form 3c–DNA complex through groove binding mode, which might block DNA replication to display their powerful antimicrobial activity.

Pd/PTABS: Catalyst for Room Temperature Amination of Heteroarenes

A mild and highly efficient catalytic amination procedure for chloroheteroarenes at ambient temperature using the Pd/PTABS catalytic system is reported. The protocol is selective for the amination of chloroheteroarenes using secondary amines such as piperidine, pyrrolidine, and several others. The exceptional mildness of the developed protocol is beneficial for the synthesis of a crucial Buparlisib intermediate as well as the formal synthesis of Alogliptin in competitive yields.

6-substituted-9H-purine derivative and preparation method and application thereof

The invention discloses a 6-substituted-9H-purine derivative and a preparation method and application thereof. The derivative has the structure shown as the formula (I). In the formula (I), R is selected from one of pyrrolidiny, furan-2-methyl, benzenesulfonyl, and substituted or unsubstituted phenyl or benzyl, wherein a substituent on phenyl or benzyl is independently selected from one or more of C1-C4 alkoxy, C1-C4 alkyl, hydroxyl, halogen and a group shown in the description, and R4 is independently selected from H or alkyl-substituted benzyl. It is shown in the experimental results that compared with 6-benzyl purine compound complex gold ions (an inhibitor 3), the 6-substituted-9H-purine derivative is higher in inhibition ratio of inflammatory factors and has better anti-inflammatory activity. The 6-substituted-9H-purine derivative has the potential as an anti-inflammatory medicine.

9-subsituted-N-(2-chlorobenzyl)purine-6-amine derivative, as well as preparation method and application thereof

The invention discloses a 9-subsituted-N-(2-chlorobenzyl)purine-6-amine derivative. The structure of the derivative is shown in a formula (I), where R is selected from a hydrogen atom, a C1-C4 alkyl group and a substituted or unsubstituted benzyl group, and a substituent on the benzyl group is one or more independently selected from halogen, -CF3, a C1-C4 alkoxy group, a C1-C4 alkyl group and a nitro group; R4 is a substituted or unsubstituted phenyl group or benzyl group, and a substituent on the phenyl group or the benzyl group is one or more of halogen and a methoxy group. Compared with a 6-benyl adenine compound complex gold ion (inhibitor 3), the 9-subsituted-N-(2-chlorobenzyl)purine-6-amine derivative is proved by testing results to have the advantages of higher inflammation factor inhibition rate, higher anti-inflammation activity and potential for use as an anti-inflammation medicament. (The formula (I) is shown in the description.).

Synthesis of Chiral Cyclopropyl Carbocyclic Purine Nucleosides via Asymmetric Intramolecular Cyclopropanations Catalyzed by a Chiral Ruthenium(II) Complex

The synthesis of chiral cyclopropyl carbocyclic purine nucleoside analogues via the highly enantioselective intramolecular cyclopropanation reactions has been reported. With a chiral ruthenium(II)-phenyloxazoline complex as the catalyst, cyclopropyl carbocyclic purine nucleoside analogues containing three contiguous stereocenters were obtained with up to 99% yield and 99% ee. Furthermore, a chiral cyclopropyl carbocyclic adenosine nucleoside having anti-BLV activity could be synthesized in a concise manner using this strategy. (Figure presented.).