1928-81-0

Basic information

• Product Name: 6-PIPERIDINOPURINE
• Synonyms: 6-PIPERIDINOPURINE;6-PIPERIDINO-1-PURINE
• CAS NO: 1928-81-0
• Molecular Formula: C₁₀H₁₃N₅
• Molecular Weight: 203.24
• Mol File: 1928-81-0.mol

Chemical Properties

• Boiling Point: 330.8°Cat760mmHg
• Flash Point: 153.8°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 1.27E-09mmHg at 25°C
• Refractive Index: 1.672
• CAS DataBase Reference: 6-PIPERIDINOPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-PIPERIDINOPURINE(1928-81-0)
• EPA Substance Registry System: 6-PIPERIDINOPURINE(1928-81-0)

Safety Data

• Hazardous Substances Data: 1928-81-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
6-PIPERIDINOPURINE is utilized as a key building block in the creation of various pharmaceuticals, specifically for the development of antiviral and anticancer agents. Its unique structure allows for the design of compounds that can target specific biological pathways, thereby enhancing the effectiveness of treatments in these areas.
Used in Antiviral Applications:
In the field of antiviral drug development, 6-PIPERIDINOPURINE is employed as a precursor for the synthesis of compounds that can inhibit viral replication and reduce the severity of viral infections. Its incorporation into antiviral medications aims to provide new treatment options for patients suffering from viral diseases.
Used in Anticancer Applications:
6-PIPERIDINOPURINE also serves as a component in the synthesis of anticancer drugs, where it contributes to the development of molecules that can target and eliminate cancer cells while minimizing damage to healthy cells. This application underscores its potential in advancing cancer therapies.
Used in Central Nervous System Disorder Treatment:
6-PIPERIDINOPURINE is studied for its potential as a receptor agonist in the treatment of central nervous system disorders. Its use in this context is aimed at modulating specific receptors to alleviate symptoms and improve the quality of life for patients with such disorders.

InChI:InChI=1/C10H13N5/c1-2-4-15(5-3-1)10-8-9(12-6-11-8)13-7-14-10/h6-7H,1-5H2,(H,11,12,13,14)

Upstream product

• 110-89-4 piperidine 
• 608-09-3 (7⁽⁹⁾H-purin-6-ylsulfanyl)-acetic acid 
• 4854-10-8 2-chloro-6-piperidin-1-yl-7⁽⁹⁾H-purine 
• 99988-37-1 2-methylsulfanyl-6-piperidino-7⁽⁹⁾H-purine 
• 4010-80-4 2,8-dichloro-6-piperidin-1-yl-7⁽⁹⁾H-purine 
• 87-42-3 6-chloro-7H-purine 
• 2562-52-9 2,6,8-trichloro-7H-purine 
• 68-94-0 hypoxanthine 
• 87-42-3 6-chloropurine 
• 81693-59-6 5-amino-4-(cyanoformimidoyl)-1H-imidazole 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 

Downstream Products

• 101155-42-4 Phosphoric acid (3aR,4R,6S,6aR)-2,2-dimethyl-6-(6-piperidin-1-yl-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 2-fluoro-phenyl ester; compound with triethyl-amine 
• 41552-92-5 6-(piperidin-1-yl)-9-(β-D-ribofuranosyl)purine 

Relevant articles and documents

6-Substituted purines as ROCK inhibitors with anti-metastatic activity

Rho-associated serine/threonine kinases (ROCKs) are principal regulators of the actin cytoskeleton that regulate the contractility, shape, motility, and invasion of cells. We explored the relationships between structure and anti-ROCK2 activity in a group

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.

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.).

Use of Purine Derivatives as HSP90 Protein Inhibitors

This invention relates to methods of inhibiting the Hsp90 chaperone protein, and methods of treatment comprising administration of compounds of formula (IA) (IB) and (II)

Identification of 4-(4-aminopiperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidines as selective inhibitors of protein kinase B through fragment elaboration

Fragment-based screening identified 7-azaindole as a protein kinase B inhibitor scaffold. Fragment elaboration using iterative crystallography of inhibitor-PKA-PKB chimera complexes efficiently guided improvements in the potency and selectivity of the compounds, resulting in the identification of nanomolar 6-(piperidin-1-yl)purine, 4-(piperidin-1-yl)-7-azaindole, and 4-(piperidin-1-yl)pyrrolo[2,3-d]pyrimidine inhibitors of PKBβ with antiproliferative activity and showing pathway inhibition in cells. A divergence in the binding mode was seen between 4-aminomethylpiperidine and 4-aminopiperidine containing molecules. Selectivity for PKB vs PKA was observed with 4-aminopiperidine derivatives, and the most PKB-selective inhibitor (30-fold) showed significantly different bound conformations between PKA and PKA-PKB chimera.