220036-08-8

Basic information

• Product Name: NU 6027
• Synonyms: 2,6-DiaMino-4-(cyclohexylMethoxy)-5-nitrosopyriMidine;2,4-Pyrimidinediamine, 6-(cyclohexylmethoxy)-5-nitroso-;ATR/CDK Inhibitor, NU6027
• CAS NO: 220036-08-8
• Molecular Formula: C₁₁H₁₇N₅O₂
• Molecular Weight: 251.288
• Product Categories: Inhibitors
• Mol File: 220036-08-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 252.5-253.7 °C(lit.)
• Boiling Point: 549.2°C at 760 mmHg
• Flash Point: 286°C
• Appearance: lavender/
• Density: 1.53g/cm³
• Vapor Pressure: 4.1E-12mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: 2-8°C
• Solubility: DMSO: 15 mg/mL
• PKA: 2.52±0.10(Predicted)
• CAS DataBase Reference: NU 6027(CAS DataBase Reference)
• NIST Chemistry Reference: NU 6027(220036-08-8)
• EPA Substance Registry System: NU 6027(220036-08-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 220036-08-8(Hazardous Substances Data)

Usage

Description

NU 6027 is a potent cyclin-dependent kinase (CDK) and Rad3-related kinase (ATR) inhibitor, which has demonstrated the ability to inhibit tumor cell growth. It functions by inhibiting ATR, which in turn impairs G2/M arrest and homologous recombination, leading to increased sensitivity to DNA-damaging agents and poly(ADP-ribose) polymerase (PARP) inhibitors.

Uses

Used in Pharmaceutical Industry:
NU 6027 is used as an anticancer agent for its ability to inhibit tumor cell growth. It targets CDK and ATR, which are key proteins involved in cell cycle regulation and DNA repair, making it a promising candidate for cancer treatment.
Used in Oncology Research:
NU 6027 is used as a research tool for studying the mechanisms of cell cycle regulation and DNA repair in cancer cells. Its inhibition of ATR and CDK provides valuable insights into the development of novel cancer therapeutics.
Used in Drug Development:
NU 6027 is used as a lead compound in the development of new drugs targeting CDK and ATR pathways. Its ability to increase sensitivity to DNA-damaging agents and PARP inhibitors makes it a valuable asset in the creation of combination therapies for cancer treatment.
Used in Cancer Treatment:
NU 6027 is used as a therapeutic agent in the treatment of various types of cancer. Its inhibition of ATR impairs G2/M arrest and homologous recombination, making cancer cells more susceptible to DNA-damaging agents and PARP inhibitors, potentially enhancing the effectiveness of these treatments.

InChI:InChI=1/C11H17N5O2/c12-9-8(16-17)10(15-11(13)14-9)18-6-7-4-2-1-3-5-7/h7H,1-6H2,(H4,12,13,14,15)

Upstream product

• 100-49-2 cyclohexylmethyl alcohol 
• 220036-14-6 NU₆₀₃₄ 

Downstream Products

• 1470134-25-8 5-(cyano-NNO-azoxy)-6-(cyclohexylmethoxy)pyrimidine-2,4-diamine 
• 1470134-38-3 N,N'-[6-(cyclohexylmethoxy)-5-nitrosopyrimidine-2,4-diyl]diacetamide 
• 1470134-28-1 N,N′-{6-(cyclohexylmethoxy)-5-{[(4-methylphenyl)sulfonyl]-NNO-azoxy}pyrimidine-2,4-diyl}diacetamide 
• 1470134-40-7 N-[7-(cyclohexylmethoxy)[1,2,5[oxadiazolo][3,4-d]pyrimidin-5-yl]]acetamide 
• 1470134-29-2 6-cyclohexylmethoxy-5-{[(4-methylphenyl)sulfonyl]-NNO-azoxy}pyrimidine-2,4-diamine 
• 1470134-27-0 7-(cyclohexylmethoxy)-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5-amine 
• 1470134-26-9 5-(aminocarbonyl-NNO-azoxy)-6-(cyclohexylmethoxy)pyrimidine-2,4-diamine 

Relevant articles and documents

NU-6027 Inhibits Growth of Mycobacterium tuberculosis by Targeting Protein Kinase D and Protein Kinase G

Tuberculosis (TB) is a global health concern, and this situation has further worsened due to the emergence of drug-resistant strains and the failure of BCG vaccine to impart protection. There is an imperative need to develop highly sensitive, specific dia

4-Alkoxy-2,6-diaminopyrimidine derivatives: inhibitors of cyclin dependent kinases 1 and 2.

The cyclin dependent kinase (cdk) inhibitor NU6027, 4-cyclohexylmethoxy-5-nitroso-pyrimidine-2,6-diamine (IC(50) vs cdk1/cyclinB1=2.9+/-0.1 microM and IC(50) vs cdk2/cyclinA3=2.2+/-0.6 microM), was used as the basis for the design of a series of 4-alkoxy-2,6-diamino-5-nitrosopyrimidine derivatives. The synthesis and evaluation of 21 compounds as potential inhibitors of cyclin-dependent kinases 1 and 2 is described and the structure-activity relationships relating to NU6027 have been probed. Simple alkoxy- or cycloalkoxy-groups at the O(4)-position were tolerated, with the 4-(2-methylbutoxy)-derivative (IC(50) vs cdk1/cyclinB1=12+/-2 microM and cdk2/cyclinA3=13+/-4 microM) retaining significant activity. Substitutions at the N(6) position were not tolerated. Replacement of the 5-nitroso substituent with ketone, oxime and semicarbazone groups essentially abolished activity. However, the derivative bearing an isosteric 5-formyl group, 2,6-diamino-4-cyclohexylmethoxy-pyrimidine-5-carbaldehyde, showed modest activity (IC(50) vs cdk1/cyclinB1=35+/-3 microM and cdk2/cyclinA3=43+/-3 microM). The X-ray crystal structure of the 5-formyl compound bound to cdk2 has been determined to 2.3A resolution. The intramolecular H-bond deduced from the structure with NU6027 bound to cdk2 is not evident in the structure with the corresponding formyl compound. Thus the parent compound, 4-cyclohexylmethoxy-5-nitrosopyrimidine-2,6-diamine (NU6027), remains the optimal basis for future structure-activity studies for cyclin-dependent kinase inhibitors in this series.