4939-28-0

Basic information

• Product Name: (2-METHYL-QUINOLIN-4-YL)-METHANOL
• Synonyms: (2-METHYL-QUINOLIN-4-YL)-METHANOL;(1-methylindol-2-yl)-(2-pyridin-3-yl-1,3-dithian-2-yl)methanol;(1-methylindol-2-yl)-[2-(3-pyridyl)-1,3-dithian-2-yl]methanol
• CAS NO: 4939-28-0
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21
• Mol File: 4939-28-0.mol

Chemical Properties

• Boiling Point: 594.4°Cat760mmHg
• Flash Point: 313.3°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 5.67E-15mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (2-METHYL-QUINOLIN-4-YL)-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2-METHYL-QUINOLIN-4-YL)-METHANOL(4939-28-0)
• EPA Substance Registry System: (2-METHYL-QUINOLIN-4-YL)-METHANOL(4939-28-0)

Safety Data

• Hazardous Substances Data: 4939-28-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2-METHYL-QUINOLIN-4-YL)-METHANOL is used as a medicinal compound for its anti-inflammatory and antioxidant effects, which may contribute to the development of treatments for various diseases and conditions.
Used in Drug Development:
In the field of drug development, (2-METHYL-QUINOLIN-4-YL)-METHANOL is used as a potential component in the creation of new drugs, leveraging its medicinal properties to address a range of health issues.
Used in Research and Laboratory Settings:
(2-METHYL-QUINOLIN-4-YL)-METHANOL also serves as a reagent or intermediate in the synthesis of other organic compounds, playing a crucial role in advancing chemical research and the development of novel chemical entities.
The specific applications and properties of (2-METHYL-QUINOLIN-4-YL)-METHANOL can vary based on the desired outcome and the context in which it is applied within the pharmaceutical, research, or other relevant industries.

InChI:InChI=1/C19H20N2OS2/c1-21-16-8-3-2-6-14(16)12-17(21)18(22)19(23-10-5-11-24-19)15-7-4-9-20-13-15/h2-4,6-9,12-13,18,22H,5,10-11H2,1H3

Upstream product

• 55625-40-6 methyl 2-methylquinoline-4-carboxylate 
• 67-56-1 methanol 
• 91-63-4 2-methylquinoline 
• 107-21-1 ethylene glycol 
• 634-38-8 2-methylquinoline-4-carboxylic acid 
• 91-56-5 indole-2,3-dione 
• 7120-26-5 ethyl 2-methylquinoline-4-carboxylate 

Downstream Products

• 409107-90-0 2-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-1,1-dioxo-1λ⁶-isothiazolidine-3-carboxylic acid methyl ester 
• 409108-05-0 2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzyl]-1,1-dioxo-tetrahydro-1λ⁶-thiophene-3-carboxylic acid methyl ester 
• 409107-99-9 2-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-1,1-dioxo-1λ⁶-[1,2]thiazinane-3-carboxylic acid methyl ester 
• 409107-87-5 2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzyl]-1,1-dioxo-1λ⁶-isothiazolidine-3-carboxylic acid methyl ester 
• 864779-06-6 4-(bromomethyl)-2-methylquinoline 
• 849454-47-3 5-[4-(2-methyl-quinolin-4-ylmethoxy)-phenylsulfanylmethyl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester 
• 477585-31-2 4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride salt 
• 910331-90-7 (1S,2R)-2-[4-(2-methylquinolin-4-ylmethoxyl)benzenesulfonylamino]cyclopentane carboxylic acid 
• 252919-33-8 [4-(2-methylquinolin-4-ylmethoxy)phenyl]-carbamic acid tert-butyl ester 
• 1198-37-4 2,4-dimethylquinoline 
• 288399-19-9 4-(chloromethyl)-2-methylquinoline 
• 6760-22-1 2-methylquinoline-4-carboxaldehyde 

Relevant articles and documents

The Ag-promoted α-C-H arylation of alcohols

We herein report the functionalization of α-C-H in alcohols through cross-dehydrogenative coupling reactions. Selectfluor was used as a mild oxidant. In situ-generated HF participated in the reaction and no external strong acid was necessary. A variety of heteroaryl-substituted alcohols were achieved with good yields and with good functional group tolerance.

Hydroxymethylation of quinolinesviairon promoted oxidative C-H functionalization: synthesis of arsindoline-A and its derivatives

Herein, we report a mild and efficient hydroxymethylation of quinolinesviaan iron promoted cross-dehydrogenative coupling reaction under external acid free conditions. Various hydroxyalkyl substituted quinolines were achieved in excellent yields with well tolerated functional groups. Importantly, a few of the hydroxylmethylated quinolines were further transformed into respective aldehydes, and were successfully utilized for the synthesis of alkaloid arsindoline-A and its derivatives.

Discovery of Novel Quinoline-Chalcone Derivatives as Potent Antitumor Agents with Microtubule Polymerization Inhibitory Activity

A series of novel quinoline-chalcone derivatives were designed, synthesized, and evaluated for their antiproliferative activity. Among them, compound 24d exhibited the most potent activity with IC50 values ranging from 0.009 to 0.016 μM in a panel of cancer cell lines. Compound 24d also displayed a good safety profile with an LD50 value of 665.62 mg/kg by intravenous injection, and its hydrochloride salt 24d-HCl significantly inhibited tumor growth in H22 xenograft models without observable toxic effects, which was more potent than that of CA-4. Mechanism studies demonstrated that 24d bound to the colchicine site of tubulin, arrested the cell cycle at the G2/M phase, induced apoptosis, depolarized mitochondria, and induced reactive oxidative stress generation in K562 cells. Moreover, 24d has potent in vitro antimetastasis and in vitro and in vivo antivascular activities. Collectively, our findings suggest that 24d deserves to be further investigated as a potent and safe antitumor agent for cancer therapy.

Quinoline substituted chalcone compound as well as preparation method and application thereof

The invention discloses a novel quinoline substituted chalcone compound as well as pharmaceutically acceptable salts and a preparation method thereof. The invention further discloses a pharmaceuticalcomposition which comprises a therapeutically effective amount of the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts and a pharmaceutically acceptable carrier. The invention further discloses a tubulin inhibitor which comprises the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts. The invention further disclosesapplication of the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts in preparing drugs for treating but not limited to colon cancer, leukemia, liver cancer, breast cancer and other diseases. The compound in the application shows excellent anti-tumor activity, and has more stable metabolic properties and better druggability prospect.

Preparation method of 2-methyl-4-hydroxymethyl quinoline and derivatives thereof

The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for reacting 2-methylquinoline and derivatives thereof with primary alcohol. The method is carried out by the following steps of: under the catalysis of Selectfluor/AgNO3, reacting the 2-methylquinoline and the derivatives in a primary alcohol aqueous solution, and performing column chromatography to obtain a product of dehydrogenation coupling of 4-position and alcohol compounds of the 2-methylquinoline derivatives. The method provided by the invention is carried out in a mixed solution ofwater and alcohol compounds under the catalysis of Selectfluor/AgNO3, and has the advantages of good substrate solubility, wide applicability, high reaction yield and strong controllability. The method is green and environment-friendly, and has the advantages of few side reaction products, green and high efficiency.

Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols

Nature routinely engages alcohols as leaving groups, as DNA biosynthesis relies on the removal of water from ribonucleoside diphosphates by a radical-mediated "spin-center shift" (SCS) mechanism. Alcohols, however, remain underused as alkylating agents in synthetic chemistry due to their low reactivity in two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes using alcohols as alkylating agents based on the mechanistic principle of spin-center shift. This strategy harnesses the dual activation modes of photoredox and organocatalysis, engaging the alcohol by SCS and capturing the resulting benzylic radical with a catalytically generated enamine. Mechanistic studies provide evidence for SCS as a key elementary step, identify the origins of competing reactions, and enable improvements in chemoselectivity by rational photocatalyst design.

Hydroxymethylation of Quinolines with Na2S2O8 by a Radical Pathway

Quinolines and isoquinolines were treated with Na2S2O8 in a mixture of methanol and water at 70 °C to form hydroxymethylated quinolines and isoquinolines in good to moderate yields, under transition-metal-free conditions. The formed hydroxymethyl group was smoothly converted into aldehyde, ester, amide, bromomethyl, (N,N-diethylamino)methyl, cyano, and tetrazole groups, in good yields.

Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH

Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both the solvent and the methylation source. It was found that adding dichloromethane (DCM) as a co-solvent could significantly increase the yield of the methylation products. Heteroarenes bearing various functional groups could be methylated and tri-deuteromethylated successfully. Deuterium labeling studies suggested that the newly generated methyl group in the products consisted of two hydrogens from the methyl group and one hydrogen from the OH group in MeOH.

AZA SPIRO ALKANE DERIVATIVES AS INHIBITORS OF METALLPROTEASES

The present invention provides a compound of Formula (I) or Formula (II): enantiomer, diastereomer, prodrug, solvate, metabolite, or pharmaceutically acceptable salt thereof, wherein constituent variables are provided herein. The compounds of Formula (I) and (II) are modulators of metalloproteases and are useful in treating diseases associated with metalloprotease activity such as arthritis, cancer, cardiovascular disorders, skin disorders, inflammation and allergic conditions.

Development of a suitable process for the preparation of a TNF-α converting enzyme inhibitor, WAY-281418

A suitable process for the preparation of kilogram quantities of a TNF-α converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydroge-nation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.