755039-53-3

Basic information

• Product Name: BUTANOIC ACID, 2-[(2-CHLORO-5-NITRO-4-PYRIMIDINYL)CYCLOPENTYLAMINO]-, METHYL ESTER, (2R)-
• Synonyms: BUTANOIC ACID, 2-[(2-CHLORO-5-NITRO-4-PYRIMIDINYL)CYCLOPENTYLAMINO]-, METHYL ESTER, (2R)-;(R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)butanoate
• CAS NO: 755039-53-3
• Molecular Formula: C₁₄H₁₉ClN₄O₄
• Molecular Weight: 342.78
• Mol File: 755039-53-3.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: BUTANOIC ACID, 2-[(2-CHLORO-5-NITRO-4-PYRIMIDINYL)CYCLOPENTYLAMINO]-, METHYL ESTER, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: BUTANOIC ACID, 2-[(2-CHLORO-5-NITRO-4-PYRIMIDINYL)CYCLOPENTYLAMINO]-, METHYL ESTER, (2R)-(755039-53-3)
• EPA Substance Registry System: BUTANOIC ACID, 2-[(2-CHLORO-5-NITRO-4-PYRIMIDINYL)CYCLOPENTYLAMINO]-, METHYL ESTER, (2R)-(755039-53-3)

Safety Data

• Hazardous Substances Data: 755039-53-3(Hazardous Substances Data)

Upstream product

• 755039-52-2 (R)-methyl 2-(cyclopentylamino)butanoate 
• 49845-33-2 2,4-Dichloro-5-nitropyrimidine 
• 74645-03-7 (R)-2-Aminobuttersaeure-methylester 
• 120-92-3 cyclopentanone 

Downstream Products

• 755039-54-4 (R)-2-chloro-8-cyclopentyl-7-ethyl-7,8-dihydropteridin-6(5H)-one 
• 755039-55-5 (R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one 
• 755039-56-6 (R)-4-((8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxybenzoic acid 
• 1344728-02-4 (R)-N-(2-aminoethyl)-4-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-ylamino)-3-methoxybenzamide 
• 755038-02-9 4-[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)benzamide 
• 1371620-66-4 (R)-7-(2-benzyl-1H-imidazol-1-yl)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine 
• 1371620-67-5 (R)-7-(2-benzyl-1H-imidazol-1-yl)-5-cyclopentyl-4-ethyl-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine 
• 1021853-34-8 1-tert-butyl 4-[(4-{[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl]amino}-3-methoxybenzoyl)amino]piperidine-1-carboxylate 
• 1021853-33-7 4-{[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl]amino}-3-methoxy-N-piperidin-4-ylbenzamide 

Relevant articles and documents

Design, synthesis and biological evaluation of novel pteridinone derivatives possessing a sulfonyl moiety as potent dual inhibitors of PLK1 and BRD4

The simultaneous inhibition of PLK1 and BRD4 by a single molecule could lead to the development of an effective therapeutic strategy for a variety of diseases in which PLK1 and BRD4 are implicated. Herein, two series of novel pteridinone derivatives possessing a sulfonyl moiety were designed, synthesized and evaluated for their biological activity. Most compounds exhibited moderate to excellent cytotoxic activity against HCT116, PC3 and BT474 cell lines. Among them, the most promising compound B2 showed high antiproliferative effects on the three cell lines with IC50 values of 0.30 μM, 1.82 μM and 1.69 μM, respectively. In the enzymatic assay, B2 was identified as a potent PLK1 and BRD4 dual inhibitor (PLK1 IC50 = 6.3 nM, BRD4 IC50 = 179 nM). Further explorations in bioactivity were conducted to clarify the anticancer mechanism of compound B2. The results showed that compound B2 obviously inhibited the proliferation of HCT116 cell lines, induced a great decrease in the mitochondrial membrane potential leading to apoptosis of HCT116 cells and arrested the G2 phase of HCT116 cells.

Discovery of Potent and Novel Dual PARP/BRD4 Inhibitors for Efficient Treatment of Pancreatic Cancer

Targeting poly(ADP-ribose) polymerase1/2 (PARP1/2) is a promising strategy for the treatment of pancreatic cancer with breast cancer susceptibility gene (BRCA) mutation. Inducing the deficiency of homologous recombination (HR) repair is an effective way t

Designing Dual Inhibitors of Anaplastic Lymphoma Kinase (ALK) and Bromodomain-4 (BRD4) by Tuning Kinase Selectivity

Concomitant inhibition of anaplastic lymphoma kinase (ALK) and bromodomain-4 (BRD4) is a potential therapeutic strategy for targeting two key oncogenic drivers that co-segregate in a significant fraction of high-risk neuroblastoma patients, mutation of ALK and amplification of MYCN. Starting from known dual polo-like kinase (PLK)-1-BRD4 inhibitor BI-2536, we employed structure-based design to redesign this series toward compounds with a dual ALK-BRD4 profile. These efforts led to compound (R)-2-((2-ethoxy-4-(1-methylpiperidin-4-yl)phenyl)amino)-7-ethyl-5-methyl-8-((4-methylthiophen-2-yl)methyl)-7,8-dihydropteridin-6(5H)-one (16k) demonstrating improved ALK activity and significantly reduced PLK-1 activity, while maintaining BRD4 activity and overall kinome selectivity. We demonstrate the compounds' on-target engagement with ALK and BRD4 in cells as well as favorable broad kinase and bromodomain selectivity.