39639-45-7

Basic information

• Product Name: (2-chloro-purin-6-yl)-cyclohexyl-amine
• Synonyms: (2-chloro-purin-6-yl)-cyclohexyl-amine
• CAS NO: 39639-45-7
• Molecular Weight: 251.719
• Mol File: 39639-45-7.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: (2-chloro-purin-6-yl)-cyclohexyl-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (2-chloro-purin-6-yl)-cyclohexyl-amine(39639-45-7)
• EPA Substance Registry System: (2-chloro-purin-6-yl)-cyclohexyl-amine(39639-45-7)

Safety Data

• Hazardous Substances Data: 39639-45-7(Hazardous Substances Data)

Upstream product

• 108-91-8 cyclohexylamine 
• 5451-40-1 2,6-dichloro-7H-purine 
• 146196-11-4 2-chloro-6-(cyclohexylamino)-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-9H-purine 
• 5451-40-1 2,6 dichloropurine 

Downstream Products

• 669003-60-5 (2-chloro-9-cyclopentyl-purin-6-yl)-cyclohexyl-amine 
• 669003-63-8 [2-chloro-9-(2-chloro-ethyl)-purin-6-yl]-cyclohexyl-amine 
• 1007555-97-6 C₁₇H₂₄ClN₅ 
• 1007555-98-7 C₁₈H₂₀ClN₅ 
• 1007555-99-8 C₁₄H₂₀ClN₅ 
• 1063332-09-1 cyclohexyl-[2-(3,5-dimethyl-pyrazol-1-yl)-9H-purin-6-yl]-amine 
• 1246532-45-5 2-chloro-N-cyclohexyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine 
• 1310346-61-2 C₂₀H₂₄N₆O₂ 
• 1246529-32-7 MPI-0479605 
• 1246533-01-6 N₂-(4-bromo-2-methoxy-phenyl)-N₆-cyclohexyl-9H-purine-2,6-diamine 
• 778603-83-1 {2-chloro-9-[2-(4-methyl-piperazin-1-yl)-ethyl]-9H-purin-6-yl}-cyclohexyl-amine 
• 1026173-33-0 (2-chloro-9-{2-[(2-methoxy-ethyl)-methyl-amino]-ethyl}-9H-purin-6-yl)-cyclohexyl-amine 
• 1246533-15-2 C₃₀H₄₁N₇O₄ 
• 1246533-12-9 C₂₉H₃₉N₇O₄ 

Relevant articles and documents

Synthesis of 2,6-diamino-substituted purine derivatives and evaluation of cell cycle arrest in breast and colorectal cancer cells

Reversine is a potent antitumor 2,6-diamino-substituted purine acting as an Aurora kinases inhibitor and interfering with cancer cell cycle progression. In this study we describe three reversine-related molecules, designed by docking calculation, that present structural modifications in the diamino units at positions 2 and 6. We investigated the conformations of the most stable prototropic tautomers of one of these molecules, the N6-cyclohexyl-N6-methyl-N2-phenyl-7H-purine-2,6-diamine (3), by Density Functional Theory (DFT) calculation in the gas phase, water and chloroform, the last solvent considered to give insights into the detection of broad signals in NMR analysis. In all cases the HN(9) tautomer resulted more stable than the HN(7) form, but the most stable conformations changed in different solvents. Molecules 1-3 were evaluated on MCF-7 breast and HCT116 colorectal cancer cell lines showing that, while being less cytotoxic than reversine, they still caused cell cycle arrest in G2/M phase and polyploidy. Unlike reversine, which produced a pronounced cell cycle arrest in G2/M phase in all the cell lines used, similar concentrations of 1-3 were effective only in cells where p53 was deleted or down-regulated. Therefore, our findings support a potential selective role of these structurally simplified, reversine-related molecules in p53-defective cancer cells.

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.

INHIBITORS OF BRUTON'S TYROSINE KINASE

This application discloses compounds according to generic Formula (I) wherein all variables are defined as described herein, which inhibit BTK. The compounds disclosed herein are useful to modulate the activity of BTK and treat diseases associated with ex