186692-41-1

Usage

Uses

Used in Pharmaceutical Research and Development:
N-BENZYL-2-CHLORO-9-ISOPROPYL-9H-PURIN-6-AMINE is utilized as a chemical intermediate for the synthesis of new drugs targeting purine receptors or enzymes. Its unique structure allows for the modulation of biological activities related to purine metabolism, which is crucial for the treatment of various diseases associated with purine dysregulation.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, N-BENZYL-2-CHLORO-9-ISOPROPYL-9H-PURIN-6-AMINE serves as a valuable compound for the design and optimization of therapeutic agents. Its structural features enable the exploration of new chemical space and the potential discovery of innovative drug candidates with improved efficacy and selectivity.
Used in Drug Discovery:
N-BENZYL-2-CHLORO-9-ISOPROPYL-9H-PURIN-6-AMINE is employed as a lead compound in drug discovery efforts. Its unique chemical properties and interactions with purine-related targets make it a promising starting point for the development of new therapeutic agents with potential applications in treating diseases related to purine metabolism.
Used in Biochemical Research:
In biochemical research, N-BENZYL-2-CHLORO-9-ISOPROPYL-9H-PURIN-6-AMINE is used as a tool compound to study the function and regulation of purine receptors and enzymes. Its ability to modulate purine-related pathways provides insights into the underlying mechanisms of purine metabolism and its role in various physiological and pathological processes.
Overall, N-BENZYL-2-CHLORO-9-ISOPROPYL-9H-PURIN-6-AMINE is a versatile and promising compound with diverse applications in the fields of medicinal chemistry, drug discovery, and biochemical research, offering opportunities for the development of novel therapeutic agents targeting purine-related diseases.

Upstream product

• 39639-47-9 N⁶-benzyl-2-chloroadenine 
• 75-26-3 isopropyl bromide 
• 100-46-9 benzylamine 
• 203436-45-7 2,6-dichloro-9-isopropyl-9H-purine 
• 3287-99-8 benzylamine hydrochloride 
• 5451-40-1 2,6-dichloro-7H-purine 
• 5167-14-6 hypoxanthine 1-N-oxide 
• 5451-40-1 2,6 dichloropurine 
• 700-02-7 adenine 1-oxide 

Downstream Products

• 186692-44-4 roscovitine 
• 186692-46-6 roscovitine 
• 186692-45-5 (S)-roscovitine 
• 158982-15-1 N9-Isopropyl olomoucine 
• 189232-42-6 bohemine 
• 1061331-94-9 cis-[PtCl₂(2-chloro-6-(benzylamino)-9-isopropylpurine)2] 
• 1061331-94-9 trans-[PtCl₂(2-chloro-6-(benzylamino)-9-isopropylpurine)2] 
• 932748-82-8 C₁₈H₂₃ClN₆ 

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.].

Adamantane-substituted purines and their β-cyclodextrin complexes: Synthesis and biological activity

Cyclin-dependent kinases (CDKs) play an important role in the cell-division cycle. Synthetic inhibitors of CDKs are based on 2,6,9-trisubstituted purines and are developed as potential anticancer drugs; however, they have low solubility in water. In this

Synthesis and pharmacophore modelling of 2,6,9-trisubstituted purine derivatives and their potential role as apoptosis-inducing agents in cancer cell lines

Twelve compounds were obtained by a three step synthetic procedure using microwave irradiation in a pivotal step. All compounds were evaluated in vitro to determine their potential effect on cell toxicity by the MTT method and flow cytometry analysis on four cancer cells lines and Vero cells. Three out of twelve compounds were found to be promising agents compared to a known and effective anticancer drug, etoposide, in three out of four cancer cell lines assayed with considerable selectivity. Preliminary flow cytometry data suggests that compounds mentioned above induce apoptosis on these cells. The main structural requirements for their activity for each cancer cell line were characterized with a preliminary pharmacophore model, which identified aromatic centers, hydrogen acceptor/donor center and a hydrophobic area. These features were consistent with the cytotoxic activity of the assayed compounds.

The first iron(III) complexes with cyclin-dependent kinase inhibitors: Magnetic, spectroscopic (IR, ES+ MS, NMR, 57Fe M?ssbauer), theoretical, and biological activity studies

The first FeIII complexes 1-6 with cyclin-dependent kinase (CDK) inhibitors of the type [Fe(Ln)Cl3]·nH2O (n=0 for 1, 1 for 2, 2 for 3-6; L1-L6=C2- and phenyl-substituted CDK inhibitors derived from 6-benzylamino-9-isopropylpurine), have been synthesized and characterized by elemental analysis, IR, 57Fe Mo?ssbauer, 1H and 13C NMR, and ES+ mass spectroscopies, conductivity and magnetic susceptibility measurements, and thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The study revealed that the compounds are mononuclear, tetrahedral high-spin (S=5/2) FeIII complexes with an admixture of an S=3/2 spin state originating probably from five-coordinated FeIII ions either connecting with a bidentate coordination mode of the CDK inhibitor ligand or relating to the possibility that one crystal water molecule enters the coordination sphere of the central atom in a portion of molecules of the appropriate complex. Nearly spin-only value of the effective magnetic moment (5.82μeff/μB) was determined for compound 1 due to absence of crystal water molecule(s) in the structure of the complex. Based on NMR data and DFT calculations, we assume that the appropriate organic ligand is coordinated to the FeIII ion through the N7 atom of a purine moiety. The cytotoxicity of the complexes was tested in vitro against selected human cancer cell lines (G-361, HOS, K-562 and MCF-7) along with the ability to inhibit the CDK2/cyclinE kinase. The best cytotoxicity (IC50: 4-23μM) and inhibition activity (IC50: 0.02-0.09μM) results have been achieved in the case of complexes 2-4, and complexes 3, 4 and 6, respectively. In addition, the X-ray structure of 2-chloro-6-benzylamino-9-isopropylpurine, i.e. a precursor for the preparation of L1, L4 and L5, is also described.

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.

6,9-DISUBSTITUTED 2- TRANS-(4- AMINOCYCLOHEXYL) AMINO]PURINES

The present invention provides novel compounds of formula (I) wherein R is selected from the group consisting of R2, R2NH-, or H2N-R3- wherein R2 is selected from the group consisting of C1-C8 alkyl and formula (II), wherein Z is selected from the group c

6,9,-disubstituted 2-[trans-(4-aminocyclohexyl) amino] purines

The present invention provides novel compounds of the formula (I) wherein R is selected from the group consisting of R2, R2NH—, or H2N—R3— wherein R2 is selected from the group consisting of C1-C8alkyl and ?wherein Z is selected from the group consisting of phenyl, heterocycle and cycloalkyl, each R4 is independently hydrogen or C1-C4alkyl, and n is an integer 1-8; wherein each C1-C8alkyl and Z is optionally substituted with 1 to 3 substituents, which may be the same or different, selected from the group consisting of Ha1, OH, and C1-C4alkyl; R3 is C1-C8alkylene; and R1 is selected from the group consisting of cyclopentyl and isopropyl, and the pharmaceutically acceptable salts, optical isomers, and hydrates thereof. In addition, the present invention provides a method of inhibiting cell cycle progression. More specifically, the present invention provides a method of inhibiting cyclin dependent kinases, particularly cdk-2. The present invention also provides a method of preventing apoptosis in neuronal cells and a method of inhibiting the development of neoplasms. In addition, the present invention provides a composition comprising an assayable amount of a compound of Formula (I) in admixture or otherwise in association with an inert carrier. The present invention also provides a pharmaceutical composition comprising an effective inhibitory amount of a compound of Formula (I) in admixture or otherwise in association with one or more pharmaceutically acceptable carriers or excipients.

Purine derivatives having, in particular, antiproliferative properties, and their biological uses

This invention provides 2-, 6, and 9-substituted purine derivatives having, in particular, antiproliferative properties, and suitable for use as pharmaceutical compositions and herbicidal compositions. Also provided are pharmaceutical compositions and her

Cyclin dependent kinase inhibitor

The present invention is based on the method of treating a patient suffering from leukemia comprising administering a therapeutically effective amount of the compound 2-([(3-hydroxypropyl)amino]-6-benzylamino)-9-isopropylpurine or a pharmaceutically accep

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.