1140-81-4

Basic information

• Product Name: 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE
• Synonyms: 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE;N-(4-Hydroxy-2-methyl-6-quinolinyl)acetamide;N-Acetyl-4-hydroxy-2-methyl-6-quinolinamine;N-(4-hydroxy-2-Methylquinolin-6-yl)acetaMide
• CAS NO: 1140-81-4
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.23588
• Mol File: 1140-81-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 442 °C at 760 mmHg
• Flash Point: 191.6 °C
• Appearance: /
• Density: 1.248 g/cm³
• Vapor Pressure: 5.19E-08mmHg at 25°C
• Refractive Index: 1.615
• Solubility: Ethyl Acetate; Toluene
• PKA: 4.29±0.40(Predicted)
• CAS DataBase Reference: 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE(1140-81-4)
• EPA Substance Registry System: 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE(1140-81-4)

Safety Data

• Hazardous Substances Data: 1140-81-4(Hazardous Substances Data)

Usage

Description

6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE, also known as N-(4-Hydroxy-2-methyl-6-quinolinyl)acetamide, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique molecular structure, which includes a quinoline ring with a hydroxyl group, a methyl group, and an acetamido group. This structure endows it with specific chemical properties and reactivity, making it a valuable building block in the development of new drugs and therapeutic agents.

Uses

Used in Pharmaceutical Synthesis:
6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE is used as an intermediate in the synthesis of NSC 23766 (N900280), a highly soluble and membrane permeable Rac GTPase inhibitor. It plays a vital role in the development of this compound, which has potential applications in the treatment of various diseases and conditions.
Used in Cancer Research and Treatment:
In the field of cancer research, 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE is used as a precursor for the synthesis of NSC 23766, which has demonstrated the ability to inhibit the anchorage-independent growth and invasion phenotypes of human prostate cancer PC-3 cells. This makes it a promising candidate for further research and development in the fight against prostate cancer.
Used in Drug Design and Development:
The unique molecular structure of 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE allows it to be used as a building block in the design and development of new drugs and therapeutic agents. Its reactivity and chemical properties can be exploited to create novel compounds with potential applications in various therapeutic areas, including oncology, cardiovascular disease, and neurological disorders.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 4065, 1948 DOI: 10.1021/ja01192a031

InChI:InChI=1/C12H12N2O2/c1-7-5-12(16)10-6-9(14-8(2)15)3-4-11(10)13-7/h3-6H,1-2H3,(H,13,16)(H,14,15)

Upstream product

• 1131-34-6 6-amino-2-methylquinolin-4-ol 
• 108-24-7 acetic anhydride 
• 63304-45-0 (E)-ethyl 3-((4-acetamidophenyl)amino)but-2-enoate 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 244219-89-4 methyl 3-{[4-(acetylamino) phenyl]amino}but-2-enoate 

Downstream Products

• 100795-23-1 N-(4-methoxy-2-methyl-6-quinolyl)acetamide 
• 1131-34-6 6-amino-2-methylquinolin-4-ol 
• 59611-57-3 6-acetamide-4-chloro-2-methylquinoline 
• 5443-31-2 2-methyl-quinoline-4,6-diamine 
• 6269-68-7 NSC 33350 
• 244218-93-7 N-(4-amino-2-methylquinoline-6-yl)-2-((4-ethylphenoxy)methyl)benzamide 

Relevant articles and documents

Design, synthesis and anti leukemia cells proliferation activities of pyrimidylaminoquinoline derivatives as DOT1L inhibitors

A series of novel pyrimidylaminoquinoline derivatives 8(a-i) and 9(a-i) containing amino side chain, and the bisaminoquinoline analogs 3(b-e) have been designed and synthesized by structural modifications on a lead DOT1L inhibitor, 3a. All the compounds have been evaluated for their DOT1L inhibitory activities. The results showed that most of the compounds have strong anti DOT1L activities. Compounds 3e, 8h and 9e are the most potential ones from each category with the IC50 values of 1.06 ± 0.35 μM, 5.72 ± 1.56 μM and 3.55 ± 1.28 μM, respectively. Such inhibitors expressed significant binding interactions with DOT1L by surface plasmon resonance (SPR)-based binding assay. The results of molecular docking experiments suggested that they could occupy the SAM binding pocket of DOT1L. Compounds 8h and 9e exhibited better inhibitory activities but poor selectivities against the both MLL-rearranged MV4-11 cells and the non MLL-rearranged Kasumi-1 cells than those of 3a and 3e, which suggested that the introduction of the amino side chain would be beneficial for their anti leukemia cells proliferation activities, possibly due to the improvement of the fat solubility. Additionally, the direct cellular inhibition activities were found that compound 9e could effectively down-regulate both the level of H3k79 methylation and MLL-rearranged leukemia gene expression of Hoxa9 and Meis1 in MV4-11 in the qRT-PCR and western blot studies. These observations suggested DOT1L was one of the potential targets but perhaps not the most pivotal one for these compounds, which made their poor selectivities against leukemia cells proliferation.

GTPase inhibitors and methods of use and crystal structure of RAC-1 GTPase

The preferred embodiments generally relate to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac (Rac1, Rac2 and/or Rac3), such compositions include compounds that modulate the GTP/GDP exchan

GTPASE INHIBITORS AND METHODS OF USE

The preferred embodiments generally relate to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac (Rac1, Rac2 and/or Rac3), such compositions include compounds that modulate the GTP/GDP exchan