101622-53-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-benzylamino-9-methylpurine is used as a key intermediate in the synthesis of Olomoucine (O567000) for its potential applications in cancer research and therapy. Olomoucine, as a cyclin-dependent kinase inhibitor, is known to induce G1 arrest, which can be beneficial in controlling cell proliferation in cancer cells.
Additionally, 2-CHLORO-6-BENZYLAMINO-9-METHYLPURINE may be utilized in the development of other purine-based drugs, given its structural properties and potential interactions with cellular targets. Its role in the synthesis of bioactive molecules highlights its importance in the advancement of medicinal chemistry and drug discovery.

InChI:InChI=1/C13H12ClN5/c1-19-8-16-10-11(17-13(14)18-12(10)19)15-7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,15,17,18)

Upstream product

• 100-46-9 benzylamine 
• 5167-14-6 hypoxanthine 1-N-oxide 
• 5451-40-1 2,6 dichloropurine 
• 700-02-7 adenine 1-oxide 
• 39639-47-9 N⁶-benzyl-2-chloroadenine 
• 74-88-4 methyl iodide 
• 2382-10-7 2,6-dichloro-9-methyl-9H-purine 

Downstream Products

• 288305-89-5 (R)-6-(benzylamino)-2-[[(1-hydroxymethyl)propyl]amino]-9-methylpurine 
• 101622-51-9 olomoucine 
• 137201-13-9 2-(2-hydroxyisobutylamino)-6-benzylamino-9-methylpurine 

Relevant academic research and scientific papers

Structure-Based Optimization of Quinazolines as Cruzain and TbrCATL Inhibitors

The cysteine proteases, cruzain and TbrCATL (rhodesain), are therapeutic targets for Chagas disease and Human African Trypanosomiasis, respectively. Among the known inhibitors for these proteases, we have described N4-benzyl-N2-phenylquinazoline-2,4-diamine (compound 7 in the original publication, 1a in this study), as a competitive cruzain inhibitor (Ki = 1.4 μM). Here, we describe the synthesis and biological evaluation of 22 analogs of 1a, containing modifications in the quinazoline core, and in the substituents in positions 2 and 4 of this ring. The analogs demonstrate low micromolar inhibition of the target proteases and cidal activity against Trypanosoma cruzi with up to two log selectivity indices in counterscreens with myoblasts. Fourteen compounds were active against Trypanosoma brucei at low to mid micromolar concentrations. During the optimization of 1a, structure-based design and prediction of physicochemical properties were employed to maintain potency against the enzymes while removing colloidal aggregator characteristics observed for some molecules in this series.

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.

CALCIUM CHANNEL AGONISTS

Embodiments of calcium channel agonists, as well as methods of making and using the calcium channel agonists, are disclosed. The disclosed calcium channel agonists and corresponding salt forms have a structure according to general formula I wherein each bond depicted as " " is a single bond or a double bond as needed to satisfy valence requirements; Z1, Z2, Z3, Z4, and Z5 independently are nitrogen or carbon; R1 and R3 are alkyl; R2 is alkyl, aryl, heteroaryl, arylalkyl, or heteroarylalkyl; and R4 is alkyl or hydroxyalkyl.

Synthesis and biological evaluation of a selective N- and P/Q-Type calcium channel agonist

The acute effect of the potent cyclin-dependent kinase (cdk) inhibitor (R)-roscovitine on Ca2+ channels inspired the development of structural analogues as a potential treatment for motor nerve terminal dysfunction. On the basis of a versatile chlorinated purine scaffold, we have synthesized ca. 20 derivatives and characterized their N-type Ca2+ channel agonist action. Agents that showed strong agonist effects were also characterized in a kinase panel for their off-target effects. Among several novel compounds with diminished cdk activity, we identified a new lead structure with a 4-fold improved N-type Ca2+ channel agonist effect and a 22-fold decreased cdk2 activity as compared to (R)-roscovitine. This compound was selective for agonist activity on N- and P/Q-type over L-type calcium channels.

Synthesis and biological activities of C-2, N-9 substituted 6- benzylaminopurine derivatives as cyclin-dependent kinase inhibitor

In this study, C-2, N-9 substituted 6-benzylaminopurine derivatives were synthesized and their inhibitory effects on cyclin-dependent kinase (CDK2) were evaluated. The effect of substituents at the C-2 and N-9 positions of substituted purine was investigated. Among the compounds tested, compound 7b- iii (6-benzylamino-2-thiomorpholinyl-9-isopropylpurine) was the most active inhibitor (IC50 = 0.9 μM). Compound 7b-iii showed 10-fold higher activity compared to olomoucine and almost the same activity as roscovitine. Results from structure-activity relationship studies should allow the design of more potent and selective CDK inhibitors, which may provide an effective therapy for cancer or other CDK dependent diseases.

Synthesis and activity of 2,6,9-trisubstituted purines

The preparation of a series of 2,6,9-trisubstituted purines and the structure-activity data for the inhibition of cyclin dependent kinase, CDK2 are presented.

SUBSTITUTED XANTHINES AND CYTOKININ ANALOGUES AS INHIBITORS OF CYTOKININ N-GLUCOSYLATION

A series of 3-substituted xanthines, 2-(2-hydroxy-2-methylpropylamino)-9-methyl-6-benzylaminopurine and 7-benzylaminooxazolopyrimidine were synthesized as potential inhibitors of cytokinin N-glucosylation.In maize leaf segments the latter compound

INHIBITORS OF TWO ENZYMES WHICH METABOLIZE CYTOKININS

Compounds which inhibit the natural metabolic inactivation of cytokinins are cosiderable physiological significance.In this study, inhibitors have been found for two enzymes which form glucose and alanine conjugates of cytokinin bases, namely, cytokinin 7-glucosyltransferase and β-(9-cytokinin)alanine synthase.The most effective inhibitors found for the former enzyme were the cytokinin analogues 3-methyl-7-n-pentylaminopyrazolopyrimidine, which acted competitively (Ki 22 μM), and the diaminopurine, 6-benzylamino-2-(2-hydroxyethylamino)-9-methylpurine (Ki 3.3 μM).However these compounds were ineffective as inhibitors of the cytokinin-alanine sythase which was inhibited competitively by IAA (Ki 70 μM) and related compounds, especially 5,7-dichloro-IAA (Ki 0.4 μM).Certain urea derivatives were moderately effective inhibitors of the enzymes (Ki ca 100 μM). Key Word Index - Cytokinins; metabolism; cytokinin 7-glucosyltransferase; β-(9-cytokinin)alanine synthase; N6-substituted adenines; auxins; indoleacetic acid.