22917-85-7

Usage

Chemical compound

2-amino-9-propyl-3,9-dihydro-6H-purin-6-one

Classification

Purine derivative

Functional groups

Propyl group and amino group attached to the purine ring

Applications

Pharmaceuticals, synthesis of drugs and therapeutic compounds

Additional potential activities

Biological and pharmacological activities

Upstream product

• 10310-21-1 2-Amino-6-chloropurin 
• 64-18-6 formic acid 
• 77287-34-4 formamide 
• 145785-30-4 2-Amino-5-nitroso-6-propylamino-3H-pyrimidin-4-one 
• 90000-49-0 2-amino-6-(n-propylamino)pyrimidin-4(3H)-one 
• 306302-08-9 2-amino-6-(1,2,4-triazol-4-yl)-9-H-purine 
• 1904-98-9 2,6-diaminopurine 
• 131490-69-2 1-propyl-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide 
• 131490-65-8 5-<amino>-1-propyl-1H-imidazole-4-carboxamide 
• 61507-88-8 5-amino-1-propyl-1H-imidazole-4-carboxamide 

Relevant academic research and scientific papers

The discovery of purine-based agents targeting triple-negative breast cancer and the αB-crystallin/VEGF protein–protein interaction

Oestrogen receptor-negative breast cancer, particularly subtypes such as triple-negative breast cancer (TNBC, around 10–15% of cases), are characterised by poor long-term survival, poor response to therapy and early progression to metastasis. Purine-based compounds represent a privileged scaffold in anticancer drug design, with several clinically approved and experimental agents in clinical development comprising a purine core structure. In this study, a series of new purine-based compounds were synthesised; seven of the new analogues were found to significantly reduce the in vitro viability of TNBC cell lines (MDA-MB-231 and MDA-MB-436) with IC50 values of ≤50 μM. In previous work, we have proposed a new concept for targeting angiogenesis driving TNBC progression, by disrupting the protein–protein interaction between the molecular chaperone αB-crystallin (CRYAB) and VEGF. Since previous clinical studies applying anti-VEGF therapy to TNBC patients have met with limited success, we were interested to test our most promising purine analogues against CRYAB/VEGF, using a custom-designed cell-based CRYAB/VEGF165 interaction assay platform. Analogues 4e and 4f significantly reduced the interaction between CRYAB/VEGF165, and compound 4e (100 μM) was also found to decrease the levels of soluble VEGF expressed by MDA-MB-231 cells by 40%. In conclusion, these promising early activity profiles warrant further investigation to validate this concept.

Hydrogen-bonding networks of purine derivatives and their bilayers for guest intercalation

Two purine derivatives, 6-chloro-9-propyl-purin-2-amine (pr-GCl) and 6-chloro-9-pentyl-purin-2-amine (pt-GCl) have been synthesized and their crystal structures were determined by single crystal X-ray diffraction analyses. The purine rings in pr-GCl or pt-GCl form unique two-dimensional hydrogen-bonding networks which in turn stack via π-π interactions to give bilayers covered with alkyl chains. In pt-GCl, the pentyl groups interact effectively among themselves so that void space for guest molecules is not available. In contrast, pr-GCl can form host-guest co-crystals. Nuclear magnetic resonance (NMR) analyses of the pr-GCl crystals immersed in various solvents for up to 60 min indicate that aromatic molecules (benzene, xylene isomers) are better guests than aliphatic ones (n-hexane, cyclohexane, isooctane) in terms of their inclusion time and amount. Powder X-ray diffraction (PXRD) patterns for the guest-included pr-GCl crystals are quite different from the simulated one, supporting the guest diffusion into the pr-GCl crystals. The crystal structure of p-xylene@pr-GCl reveals that p-xylene molecules are intercalated between the characteristic pr-GCl bilayers that are shown in both pr-GCl and pt-GCl crystals.

HETEROCYCLIC GTP CYCLOHYDROLASE 1 INHIBITORS FOR THE TREATMENT OF PAIN

The present invention relates to the field of small molecule heterocyclic inhibitors of GTP cyclohydrolase (GCH-I), or a tautomer, prodrug, or pharmaceutically acceptable salt thereof. The invention also features pharmaceutical compositions of the compounds and the medical use of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, or neuropathic pain).

2-Amino-6-(1,2,4-triazol-4-yl)-purine: A useful intermediate in the synthesis of 9-alkylguanines

2-Amino-6-(1,2,4-triazol-4-yl)purine, prepared from 2,6-diaminopurine, was regioselectively alkylated at position 9. Subsequent alkaline hydrolysis afforded 9-alkylguanines in high yield. (C) 2000 Elsevier Science Ltd.

Alkylpurines as immunopotentiating agents. Synthesis and antiviral activity of certain alkylguanines.

Several simple 8-substituted 9-alkyl- and 7,8-disubstituted 9-alkylguanine derivatives were synthesized as potential antiviral agents. These were tested for antiviral protection against a lethal Semliki Forest virus (SFV) infection in mice, and their anti

Process for the preparation of 9-substituted guanine derivatives

A process for the preparation of 9-substituted quanine derivatives of general formula (I), in which R is C1 -C4 -alkyl optionally substituted with one or more hydroxy groups, or R is (α), benzyl, ribosyl, 2'-deoxyribosyl or (CH2)n -OR1 where n is 1 or 2, and R1 is CH2 CH2 OH or (β) or salts thereof, in which a 1-substituted5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide of general formula (III), where R has the same meaning as in formula (I), is cyclized: a) by treatment with a heavy metal salt of the group of Cu-, Ag-, Pb- and Hg-salts in an aqueous alkaline medium containing at least for equivalents of OH-ions at a temperature form about 0° C. to the reflux temperature, or b) by treatment with a peroxy compound in an aqueous alkaline medium at a temperature of about 0°-30° C., whereafter (I) is isolated by treatment with a acid and, if desired, is converted into a salt. The invention further comprises intermediates for use in the preparation of the above-mentioned compounds.