330551-07-0

Basic information

• Product Name: 4-cyclopentylamino-2-(4-(4-methylpiperazin-1-yl)phenylamino)-5-aminopyrimidine
• Synonyms: 4-cyclopentylamino-2-(4-(4-methylpiperazin-1-yl)phenylamino)-5-aminopyrimidine
• CAS NO: 330551-07-0
• Molecular Weight: 367.497
• Mol File: 330551-07-0.mol

Chemical Properties

• CAS DataBase Reference: 4-cyclopentylamino-2-(4-(4-methylpiperazin-1-yl)phenylamino)-5-aminopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-cyclopentylamino-2-(4-(4-methylpiperazin-1-yl)phenylamino)-5-aminopyrimidine(330551-07-0)
• EPA Substance Registry System: 4-cyclopentylamino-2-(4-(4-methylpiperazin-1-yl)phenylamino)-5-aminopyrimidine(330551-07-0)

Safety Data

• Hazardous Substances Data: 330551-07-0(Hazardous Substances Data)

Upstream product

• 100-00-5 4-chlorobenzonitrile 
• 16153-81-4 4-(4-Methyl-piperazino)-anilin 
• 16155-03-6 1-methyl-4-(4-nitrophenyl)piperazine 
• 350-46-9 4-Fluoronitrobenzene 
• 1003-03-8 Cyclopentamine 
• 330550-92-0 2-chloro-N-cyclopentyl-5-nitropyrimidin-4-amine 
• 109-01-3 1-methyl-piperazine 
• 330550-98-6 N⁴-cyclopentyl-N²-(4-(4-methylpiperazin-1-yl)phenyl)-5-nitropyrimidine-2,4-diamine 

Downstream Products

• 330550-46-4 8-Cyclopentyl-6methyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-8H-pteridin-7-one 
• 330550-45-3 8-Cyclopentyl-2-[[4-(4methylpiperazin-1-yl)phenyl]amino]-8H-pteridin-7-one 
• 1350544-90-9 9-cyclopentyl-N-(4-(4-methylpiperazin-1-yl)phenyl)-8-phenylamino-9H-purin-2 -amine 
• 1350545-09-3 8-(3-nitrophenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 
• 1350545-11-7 8-(3-ethynylphenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 
• 1350545-18-4 8-(3-methylphenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 
• 1350545-16-2 8-(3-hydroxyphenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 
• 1350545-17-3 8-(3-chlorophenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 
• 1350545-08-2 8-(4-bromophenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 
• 1350545-12-8 8-(2-fluoro-4-bromophenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 
• 1350545-25-3 8-(2,5-dichlorophenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 
• 1414781-75-1 C₃₄H₃₆ClN₉O 
• 1414781-76-2 C₃₄H₃₇N₉O 
• 1350545-00-4 8-(3-chloro-4-fluorophenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 

Relevant articles and documents

Synthesis and biological evaluation of 2,4-diaminopyrimidines as selective Aurora A kinase inhibitors

The Aurora kinases are a family of serine/threonine kinases that interact with components of the mitotic apparatus and serve as potential therapeutic targets in oncology. Here we synthesized 15 2,4-diaminopyrimidines and evaluated their biological activities, including antiproliferation, inhibition against Aurora kinases and cell cycle effects. These compounds generally exhibited more potent cytotoxicity against tumor cell lines compared with the VX-680 control, especially compound 11c, which showed the highest cytotoxicities, with IC50 values of 0.5-4.0 1/4M. Compound 11c had more than 35-fold more selectivity for Aurora A over Aurora B, and molecular docking analysis indicated that compound 11c form better interaction with Aurora A both from the perspective of structure and energy. Furthermore, compound 11c induced G2/M cell cycle arrest in HeLa cells. This series of compounds has the potential for further development as selective Aurora A inhibitors for anticancer activity.

Design, synthesis and antiproliferative activity of novel 2,4-diamino-5-methyleneaminopyrimidine derivatives as potential anticancer agents

In order to discover new anticancer agents, 25 novel 2,4-diamino-5-methyleneaminopyrimidine derivatives were designed and synthesized based on our previous work via a ring-opening strategy. Among them, compared with 5-FU, compound 7i exhibited 4.9-, 2.9-,

Synthesis and evaluation of 2,9-disubstituted 8-phenylthio/phenylsulfinyl-9H-purine as new EGFR inhibitors

In present study, we described the synthesis and biological evaluation of a new class of EGFR inhibitors containing 2,9-disubstituted 8-phenylthio/phenylsulfinyl-9H-purine scaffold. Thirty-one compounds were synthesized. Among them, compound C9 displayed the IC50 of 29.4 nM against HCC827 cell line and 1.9 nM against EGFRL858R. Compound C12 showed moderate inhibitory activity against EGFRL858R/T790M/C797S (IC50 = 114 nM). Western bolt assay suggested that compound C9 significantly inhibited EGFR phosphorylation. In vivo test, compound C9 remarkably exhibited inhibitory effect on tumor growth at 5.0 mg/kg by oral administration in established nude mouse HCC827 xenograft model. These results indicate that the 2,9-disubstituted 8-phenylsulfinyl/phenylsulfinyl-9H-purine derivatives can act as potent EGFR(L858R) inhibitors and effective anticancer agents. Additionally, optimization of compound C12 may result in discovering the fourth-generation EGFR-TKIs.

ARYLAMINO PURINE DERIVATIVES, PREPARATION METHOD AND PHARMACEUTICAL USE THEREOF

Arylamino purine derivatives represented by formula I and their preparation method are disclosed, wherein each substituent is defined as in the description. The derivatives have an inhibitory effect on non-small cell lung cancer with deletion mutation of exon 19 or L858R point mutation of exon 21 in epidermal growth factor receptor (EGFR).

Structural optimization and structure-activity relationships of N 2-(4-(4-methylpiperazin-1-yl)phenyl)- N 8-phenyl-9 H -purine-2,8-diamine derivatives, a new class of reversible kinase inhibitors targeting both EGFR-activating and resistance mutations

This paper describe the structural optimization of a hit compound, N 2-(4-(4-methylpiperazin-1-yl)phenyl)-N8-phenyl-9H-purine- 2,8-diamine (1), which is a reversible kinase inhibitor targeting both EGFR-activating and drug-resistance (T790M) mutations but has poor binding affinity. Structure-activity relationship studies led to the identification of 9-cyclopentyl-N2-(4-(4-methylpiperazin-1-yl)phenyl)-N 8-phenyl-9H-purine-2,8-diamine (9e) that exhibits significant in vitro antitumor potency against the non-small-cell lung cancer (NSCLC) cell lines HCC827 and H1975, which harbor EGFR-activating and drug-resistance mutations, respectively. Compound 9e was further assessed for potency and selectivity in enzymatic assays and in vivo anti-NSCLC studies. The results indicated that compound 9e is a highly potent kinase inhibitor against both EGFR-activating and resistance mutations and has good kinase spectrum selectivity across the kinome. In vivo, oral administration of compound 9e at a dose of 5 mg/kg caused rapid and complete tumor regression in a HCC827 xenograft model, and an oral dose of 50 mg/kg initiated a considerable antitumor effect in an H1975 xenograft model.

Pteridinones as kinase inhibitors

Disclosed are compounds of Formulae (Ia), (Ib), (Ic), (Id) wherein: W is NH, S, SO, or SO2; R2 is (un)substituted aryl, (un)substituted heteroaryl, or (un)substituted carbocycle or heterocycle; Q is hydrogen or lower alkyl; R4