5465-86-1

Basic information

• Product Name: 4-Methyl-2-(1-piperidinyl)-quinoline
• Synonyms: 4-Methyl-2-(1-piperidinyl)-quinoline;ML 204;NSC 25850
• CAS NO: 5465-86-1
• Molecular Formula: C15H18N2
• Molecular Weight: 226.31682
• Product Categories: Aromatics, Heterocycles, Inhibitors;Inhibitors
• Mol File: 5465-86-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 72-73 °C
• Boiling Point: 404.4°Cat760mmHg
• Flash Point: 198.3°C
• Appearance: white to beige/
• Density: 1.102g/cm³
• Vapor Pressure: 9.5E-07mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble5mg/mL at warmed (clear solution)
• PKA: 7.34±0.61(Predicted)
• CAS DataBase Reference: 4-Methyl-2-(1-piperidinyl)-quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-2-(1-piperidinyl)-quinoline(5465-86-1)
• EPA Substance Registry System: 4-Methyl-2-(1-piperidinyl)-quinoline(5465-86-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 5465-86-1(Hazardous Substances Data)

Usage

Description

4-Methyl-2-(1-piperidinyl)-quinoline, also known as ML-204, is a potent inhibitor of transient receptor potential canonical 4 (TRPC4) channels. It selectively blocks TRPC4 channels with high specificity, exhibiting selectivity against other TRPC channels such as TRPC5 and TRPC6, and does not affect other TRP channels like TRPV1, TRPV3, TRPA1, or TRPM8. 4-Methyl-2-(1-piperidinyl)-quinoline plays a crucial role in modulating various cellular responses and muscle reactions due to interactions with the environment.

Uses

Used in Pharmaceutical Applications:
4-Methyl-2-(1-piperidinyl)-quinoline is used as a pharmacological agent for targeting TRPC4 channels, which are involved in various cellular stimulation and muscle responses. Its high selectivity and potency make it a valuable tool in understanding the role of TRPC4 channels in different physiological and pathological processes.
Used in Research and Development:
In the field of research, 4-Methyl-2-(1-piperidinyl)-quinoline serves as a valuable compound for studying the function and regulation of TRPC4 channels. It can be used to investigate the molecular mechanisms underlying the activation and inhibition of these channels, as well as their contribution to various cellular processes.
Used in Drug Discovery:
4-Methyl-2-(1-piperidinyl)-quinoline can be utilized in drug discovery efforts to develop novel therapeutics targeting TRPC4 channels. Its high selectivity and potency make it an attractive starting point for the design and optimization of new drugs aimed at treating conditions associated with the dysregulation of TRPC4 channels.
Used in Ion Channel Modulation:
4-Methyl-2-(1-piperidinyl)-quinoline is used as a modulator of ion channel activity, specifically targeting TRPC4 channels. This application is relevant in the development of treatments for conditions where the regulation of ion channels is critical, such as certain neurological disorders or cardiovascular diseases.

Biochem/physiol Actions

ML204 is a potent and selective TRPC4 channel inhibitor.

InChI:InChI=1/C15H18N2/c1-12-11-15(17-9-5-2-6-10-17)16-14-8-4-3-7-13(12)14/h3-4,7-8,11H,2,5-6,9-10H2,1H3

Upstream product

• 110-89-4 piperidine 
• 634-47-9 2-chloro-4-methylquinoline 
• 5257-06-7 N-(2-acetylphenyl)formamide 
• 521270-78-0 1-(2-isocyanophenyl)ethan-1-one 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 4053-40-1 4-methylquinoline 1-oxide 
• 5542-49-4 piperidin-1-yl benzoate 
• 19343-78-3 4-methyl-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Inhibition of Yeast-to-Hypha Transition and Virulence of Candida albicans by 2-Alkylaminoquinoline Derivatives

A rapid increase in Candida albicans infection and drug resistance has caused an emergent need for new clinical strategies against this fungal pathogen. In this study, we evaluated the inhibitory activity of a series of 2-alkylaminoquinoline derivatives against C. albicans isolates. A total of 28 compounds were assessed for their efficacy in inhibiting the yeast-to-hypha transition, which is considered one of the key virulence factors in C. albicans. Several compounds showed strong activity to decrease the morphological transition and virulence of C. albicans cells. The two leading compounds, compound 1 (2-[piperidin-1-yl]quinolone) and compound 12 (6-methyl-2-[piperidin-1-yl]quinoline), remarkably attenuated C. albicans hyphal formation and cytotoxicity in a dose-dependent manner, but they showed no toxicity to either C. albicans cells or human cells. Intriguingly, compound 12 showed an excellent ability to inhibit C. albicans infection in the mouse oral mucosal infection model. This leading compound also interfered with the expression levels of hypha-specific genes in the cyclic AMP-protein kinase A and mitogen-activated protein kinase signaling pathways. Our findings suggest that 2-alkylaminoquinoline derivatives could potentially be developed as novel therapeutic agents against C. albicans infection due to their interference with the yeast-to-hypha transition.

TRPC4 MODULATORS FOR USE IN THE TREATMENT OR PREVENTION OF PAIN

The instant application discloses methods of treating, reducing, or preventing pain in a mammal, which may include administering a compound capable of modulating a transient receptor potential channel. In one aspect, the TRP channel may be TRPC4. Types of pain contemplated by the present disclosure include acute, chronic, neuropathic, and nociceptive pain.

Copper-Catalyzed Cross-Dehydrogenative Coupling of N-Iminoquinolinium Ylides with Secondary Amines

The copper-catalyzed cross-dehydrogenative coupling of N-iminoquinolinium ylides with secondary amines led to ortho-amino-substituted quinoline derivatives with high levels of regioselectivity in good yields. This direct C–H bond amination transformation employs CuI as the catalyst without the use of a ligand, external oxidant, or base. The reaction is operationally simple and can be conducted under mild conditions. The N-benzoyl directing group can be removed without any additional steps.