100795-23-1

Basic information

• Product Name: N-(4-Methoxy-2-methylquinolin-6-yl)acetamide
• Synonyms: N-(4-Methoxy-2-methylquinolin-6-yl)acetamide;N-(4-methoxy-2-methyl-6-quinolinyl)Acetamide
• CAS NO: 100795-23-1
• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 230.26246
• Mol File: 100795-23-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Solubility: Ethyl Acetate; Methanol
• CAS DataBase Reference: N-(4-Methoxy-2-methylquinolin-6-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Methoxy-2-methylquinolin-6-yl)acetamide(100795-23-1)
• EPA Substance Registry System: N-(4-Methoxy-2-methylquinolin-6-yl)acetamide(100795-23-1)

Safety Data

• Hazardous Substances Data: 100795-23-1(Hazardous Substances Data)

Usage

Description

N-(4-Methoxy-2-methylquinolin-6-yl)acetamide is an organic compound that serves as an intermediate in the synthesis of NSC 23766 (N900280), a Rac GTPase inhibitor. It is characterized by its quinoline structure, which is a fused bicyclic system consisting of a six-membered aromatic ring and a partially unsaturated six-membered ring. The presence of a 4-methoxy group and a 2-methyl group on the quinoline core provides additional functionalization and steric hindrance, which may contribute to its biological activity.

Uses

Used in Pharmaceutical Industry:
N-(4-Methoxy-2-methylquinolin-6-yl)acetamide is used as an intermediate in the synthesis of NSC 23766, a Rac GTPase inhibitor. Rac GTPases are small molecular switches that play a crucial role in various cellular processes, including cell migration, adhesion, and invasion. Inhibition of Rac GTPase has been shown to suppress the anchorage-independent growth and invasion phenotypes of human prostate cancer PC-3 cells, making it a potential therapeutic target for cancer treatment.
Used in Cancer Research:
N-(4-Methoxy-2-methylquinolin-6-yl)acetamide is used as a precursor for the development of NSC 23766, which has demonstrated inhibitory effects on the anchorage-independent growth and invasion phenotypes of human prostate cancer PC-3 cells. This suggests that N-(4-Methoxy-2-methylquinolin-6-yl)acetamide may contribute to the development of novel therapeutic agents for the treatment of prostate cancer and potentially other cancer types.
Used in Drug Synthesis:
N-(4-Methoxy-2-methylquinolin-6-yl)acetamide is used as a key intermediate in the synthesis of NSC 23766, a Rac GTPase inhibitor. Its unique quinoline structure and functional groups make it a valuable building block for the development of new drugs targeting Rac GTPase and other related pathways. The synthesis of NSC 23766 from N-(4-Methoxy-2-methylquinolin-6-yl)acetamide may involve various chemical reactions, such as amide coupling, acylation, or other functional group transformations, to achieve the desired biological activity.

Upstream product

• 1140-81-4 N-(4-hydroxy-2-methylquinolin-6-yl)acetamide 
• 77-78-1 dimethyl sulfate 
• 59611-57-3 6-acetamide-4-chloro-2-methylquinoline 
• 124-41-4 sodium methylate 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 63304-45-0 (E)-ethyl 3-((4-acetamidophenyl)amino)but-2-enoate 

Downstream Products

• 60504-61-2 N,N'-bis-(6-amino-2-methyl-[4]quinolyl)-hexanediyldiamine 
• 5443-31-2 2-methyl-quinoline-4,6-diamine 
• 137872-98-1 6-acetamido-4-(benzylamino)-2-methylquinoline hydrochloride 
• 6269-68-7 NSC 33350 
• 244218-93-7 N-(4-amino-2-methylquinoline-6-yl)-2-((4-ethylphenoxy)methyl)benzamide 

Relevant articles and documents

Small molecule antagonists of cell-surface heparan sulfate and heparin-protein interactions

Surfen, bis-2-methyl-4-amino-quinolyl-6-carbamide, was previously reported as a small molecule antagonist of heparan sulfate (HS), a key cell-surface glycosaminoglycan found on all mammalian cells. To generate structure-activity relationships, a series of rationally designed surfen analogs was synthesized, where its dimeric structure, exocyclic amines, and urea linker region were modified to probe the role of each moiety in recognizing HS. An in vitro assay monitoring inhibition of fibroblast growth factor 2 binding to wild-type CHO cells was utilized to quantify interactions with cell surface HS. The dimeric molecular structure of surfen and its aminoquinoline ring systems was essential for its interaction with HS, and certain dimeric analogs displayed higher inhibitory potency than surfen and were also shown to block downstream FGF signaling in mouse embryonic fibroblast cells. These molecules were also able to antagonize other HS-protein interactions including the binding of soluble RAGE to HS. Importantly, selected molecules were shown to neutralize heparin and other heparinoids, including the synthetic pentasaccharide fondaparinux, in a factor Xa chromogenic assay and in vivo in mice. These results suggest that small molecule antagonists of heparan sulfate and heparin can be of therapeutic potential for the treatment of disorders involving glycosaminoglycan-protein interactions.

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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