39639-47-9

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzyl-2-chloro-9H-purin-6-amine is used as an intermediate in the synthesis of Olomoucine (O567000), a purine derivative with significant biological activity. Olomoucine is known to inhibit cyclin-dependent kinases, which play a crucial role in regulating cell cycle progression. By inhibiting these kinases, Olomoucine can induce G1 arrest, effectively halting the cell cycle and preventing uncontrolled cell proliferation, a hallmark of cancer. This makes N-Benzyl-2-chloro-9H-purin-6-amine an essential component in the development of potential anticancer drugs.
Additionally, due to its unique chemical structure, N-Benzyl-2-chloro-9H-purin-6-amine may also be used as a building block for the synthesis of other purine-based compounds with various applications in the pharmaceutical industry, such as antiviral, anti-inflammatory, and immunosuppressive agents.

InChI:InChI=1/C12H10ClN5/c13-12-17-10(9-11(18-12)16-7-15-9)14-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H2,14,15,16,17,18)

Upstream product

• 5451-40-1 2,6 dichloropurine 
• 100-46-9 benzylamine 
• 700-02-7 adenine 1-oxide 
• 100-39-0 benzyl bromide 
• 149948-29-8 C₈H₉ClN₆ 
• 190962-00-6 6-chloro-2-formylaminopurine acetate 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 10310-21-1 2-Amino-6-chloropurin 
• 5451-40-1 2,6-dichloro-7H-purine 
• 5167-14-6 hypoxanthine 1-N-oxide 

Downstream Products

• 186692-41-1 2-chloro-6-phenylmethylamino-9-iso-propylpurine 
• 70608-06-9 2-(2-hydroxyethylamino)-6-benzylaminopurine 
• 39639-54-8 N²,N⁶-dibenzyl-7⁽⁹⁾H-purine-2,6-diamine 
• 101622-53-1 2-chloro-6-benzylamino-9-methylpurine 
• 101622-51-9 olomoucine 
• 158982-15-1 N9-Isopropyl olomoucine 
• 186692-44-4 roscovitine 
• 186692-46-6 roscovitine 
• 186692-45-5 (S)-roscovitine 
• 137201-23-1 2-Aminomethyl-9-methyl-6-benzylaminopurine 
• 137201-13-9 2-(2-hydroxyisobutylamino)-6-benzylamino-9-methylpurine 
• 1012864-71-9 methyl 1-[N⁶-benzyl-2-chloroadenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate 
• 1007556-16-2 N-benzyl-9-butyl-2-chloro-9H-purin-6-amine 
• 310400-99-8 N-benzyl-2-chloro-9-cyclopentyl-9H-purin-6-amine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of seliciclib derivatives as potent and selective CDK9 inhibitors for prostate cancer therapy

Seliciclib is a cyclin-dependent kinase (CDK) inhibitor that has been assayed in phase II clinical trials as an anticancer agent. This paper describes the synthesis of novel derivatives of seliciclib with improved potency, metabolic stability, aqueous solubility, and anti-proliferative activity. The new derivatives showed a novel CDKs selectivity profile. Replacement of ethyl alcohol at position 2 of purine with dimethylaminopropyl and fluorination of benzyl at position 6 of purine of seliciclib resulted in the formation of a derivative that potently and selectively inhibited CDK9 (26?nM vs. CDK9 and > 60-fold selectivity vs. CDK2/5/7). In comparison to seliciclib, this derivative shows lower metabolic clearance (25% lower in Clint), higher aqueous solubility and is more cytotoxic in androgen-independent prostate cancer cells. Graphic abstract: [Figure not available: see fulltext.].

COMPOUNDS AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR

The present invention provides compounds of Formula (I) shown above and their pharmaceutically acceptable salt, solvates, isomers, or prodrugs, as well as pharmaceutical compositions containing these compounds. Also provided by the invention is a method for treating a disorder mediated by macrophage migration inhibitory factor in a subject, comprising administering to the subject in need thereof a compound or a pharmaceutical composition of this invention.

Design, synthesis and biological evaluation of novel histone deacetylase1/2 (HDAC1/2) and cyclin-dependent Kinase2 (CDK2) dual inhibitors against malignant cancer

In the current study, we have designed and synthesized a series of novel histone deacetylase1/2 (HDAC1/2) and cyclin-dependent kinase2 (CDK2) dual inhibitors by integrating purine-based pharmacophore into the recognition cap group of CS055. The representative compound 14d with excellent antiproliferative activities towards five solid cancer cells, showed potent inhibitory activities against HDAC1, HDAC2 and CDK2 with IC50 values of 70.7 nM, 23.1 nM and 0.80 μM, respectively. Besides, compound 14d could effectively block the cell cycle in the G2/M phase and induce apoptosis, which might be related to increasing intracellular ROS levels. Importantly, compound 14d exhibited desirable pharmacokinetic (PK) properties with the intraperitoneal bioavailability of 50.8percent in ICR mice, and potent in vivo antitumor activity in the HCT116 xenograft model. Therefore, compound 14d could be considered as a promising lead compound for the development of multitargeting anticancer agents.

2. 6, 9 - Trisubstituted purine derivatives and its preparation method and application (by machine translation)

As shown in formula I 2, 6, 9 - trisubstituted purine derivatives and its preparation method and application, wherein R1 , R2 , R3 And R4 Such as defined in the specification. In vitro cell test demonstrate that the pharmaceutical composition can effectively inhibit the growth of a variety of tumor cells, can develop into anti-tumor drug; animal experiments prove that the said compound in vivo has obvious anti-EV71 virus, can develop into the treatment and prevention of EV71 virus infection. (by machine translation)

IMAGING AGENTS FOR NEURAL FLUX

Provided herein are radiolabeled compounds useful for non-invasive imaging techniques. An exemplary radiolabeled compound provided herein is useful as a radiotracer for positron emission tomography. The present application also provides unlabeled compounds useful in methods of treating diseases of the central nervous system or disease of the peripheral nervous system. Methods for preparing radiolabeled compounds, preparing unlabeled compounds, and diagnostic methods using labeled or unlabeled compounds are also provided.

PURINE-BASED TRIAZOLES

A pharmaceutical composition for inhibiting at least protein kinase in a cell of a subject includes a purine based triazole.

Facile synthesis of 8-azido-6-benzylaminopurine

Bromination of 6-benzylaminopurine (1) with Br2 in AcOH in the presence of AcONa afforded 6-benzylamino-8-bromopurine (2) in 59% yield. The position of bromination was confirmed by direct transformation of bromide 2 by reaction with NaN3 in dimethyl sulfoxide to 8-azido-6-benzylaminopurine (3) in a yield of 70% and comparison of its properties with the known compound 2-azido-6- benzylaminopurine (11). Compounds 3 and 11 were checked for their biological activity in specific biotests based on the primary cytokinin effects in living plants. Both synthesized compounds displayed effects similar to the typical cytokinin 6-benzylaminopurine (1). Copyright Taylor and Francis Group, LLC.

Novel purine-based fluoroaryl-1,2,3-triazoles as neuroprotecting agents: Synthesis, neuronal cell culture investigations, and CDK5 docking studies

A series of novel purine-based fluoroaryl triazoles were synthesized using the Cu(I) catalyzed 1,3-dipolar cycloaddition reactions (click reactions), and assayed for their neuroprotective effects using fluorescence electron microscopy. Among these triazoles, o-fluorophenylmetyl-triazole, 7, has comparable neuroprotective effect as that of Flavopiridol (1) and Roscovitine (2), the state of the art CDK inhibitors, against the Aβ induced neurotoxicity. These results are substantiated using computer docking methods (DarwinDock/GenDock), which predict that Roscovitine and the triazole 7 bind to the ATP-binding site of CDK5/p25 with comparable binding energies, whereas the corresponding pentafluorophenylmethyl-triazole, 9, has dramatically reduced binding energy (in accordance with its lack of neuroprotection). These combined experimental and theoretical studies support the involvement of CDK5/p25 in the neuronal cell cycle re-entry.

N-Alkylation of 2,6-dichloropurine hydrochloride with a variety of alcohols over alumina catalyst

2,6-Dichloropurine hydrochloride reacts with various types of alcohols using different alumina catalysts and converts into its N-9-alkyl-2-chloro-6- hydroxy-9H-purine products to an extent of 49-74%. The product selectivity depends on the stability of carbocation generated from the alcohol. More stable carbocation formulates both N-7 and N-9-alkyl-2,6-dichloropurine products, whereas the less stable carbocation results in exclusively N-9-alkyl-2-chloro-6- hydroxy-9H-purine. The catalytic activity of alumina prepared using the sol-gel method has larger Brunauer, Emmett, and Teller (BET) surface area and hence shows significantly greater catalytic activity than the commercially available alumina samples. Copyright

Practical synthesis of roscovitine and CR8

Roscovitine and CR8 are potent inhibitors of cyclin-dependent kinases. A scalable synthesis of both inhibitors is described. In the case of CR8, the biarylmethylamine moiety was obtained as a stable and high-purity salt.