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4-Hydroxy-6-methoxy-2-(trifluoromethyl)quinoline, commonly referred to as HMQ, is a quinoline derivative characterized by the presence of a hydroxy group at the 4-position, a methoxy group at the 6-position, and a trifluoromethyl group at the 2-position. This yellow crystalline compound serves as a crucial intermediate in the synthesis of pharmaceuticals and agrochemicals, and its unique chemical structure endows it with a range of biological activities, including antitumor and antiviral properties. Additionally, HMQ functions as a fluorescent probe for detecting metal ions in biological and environmental samples, highlighting its versatility and potential for various applications.

1701-21-9

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1701-21-9 Usage

Uses

Used in Pharmaceutical Synthesis:
4-Hydroxy-6-methoxy-2-(trifluoromethyl)quinoline is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows for the development of new compounds with potential therapeutic applications.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-Hydroxy-6-methoxy-2-(trifluoromethyl)quinoline serves as an intermediate for the production of agrochemicals, contributing to the development of new pesticides and other agricultural products.
Used in Antitumor Applications:
4-Hydroxy-6-methoxy-2-(trifluoromethyl)quinoline is used as an antitumor agent due to its demonstrated antitumor activities in some studies. It may have potential in the development of new cancer treatments.
Used in Antiviral Applications:
HMQ is used as an antiviral agent, leveraging its antiviral properties to combat viral infections, offering a potential avenue for the development of new antiviral medications.
Used in Environmental and Biological Analysis:
4-Hydroxy-6-methoxy-2-(trifluoromethyl)quinoline is used as a fluorescent probe for the detection of metal ions in biological and environmental samples. Its ability to fluoresce upon binding to metal ions makes it a valuable tool in analytical chemistry and environmental monitoring.

Check Digit Verification of cas no

The CAS Registry Mumber 1701-21-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,0 and 1 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1701-21:
(6*1)+(5*7)+(4*0)+(3*1)+(2*2)+(1*1)=49
49 % 10 = 9
So 1701-21-9 is a valid CAS Registry Number.

1701-21-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-Methoxy-2-(trifluoromethyl)quinolin-4-ol

1.2 Other means of identification

Product number -
Other names 6-methoxy-2-(trifluoromethyl)-1H-quinolin-4-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1701-21-9 SDS

1701-21-9Relevant academic research and scientific papers

New trifluoromethyl quinolone derivatives: Synthesis and investigation of antimicrobial properties

Panda, Siva S.,Jain, Subhash C.

, p. 3225 - 3229 (2013)

A series of quinolone derivatives, containing different heterocyclic amines were prepared. Synthesized compounds were evaluated for their in vitro antimicrobial activities against two Gram-positive bacteria, three Gram-negative bacteria as well as four fungi. All the derivatives showed good activity towards Gram-positive bacteria and less activity towards Gram-negative bacteria. They also showed moderate to comparable activity against Aspergillus niger and Candida albicans and low to moderate antifungal activity against Aspergillus fumigatus and Aspergillus flavus.

New quinoline-triazole conjugates: Synthesis, and antiviral properties against SARS-CoV-2

Seliem, Israa A.,Panda, Siva S.,Girgis, Adel S.,Moatasim, Yassmin,Kandeil, Ahmed,Mostafa, Ahmed,Ali, Mohamed A.,Nossier, Eman S.,Rasslan, Fatma,Srour, Aladdin M.,Sakhuja, Rajeev,Ibrahim, Tarek S.,Abdel-samii, Zakaria K.M.,Al-Mahmoudy, Amany M.M.

, (2021/07/02)

At present therapeutic options for severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) are very limited. We designed and synthesized three sets of small molecules using quinoline scaffolds. A series of quinoline conjugates (10a-l, 11a-c, and 12a-

2 -trifluoromethyl -4 - amino - quinoline derivative and application thereof

-

Paragraph 0032-0036, (2021/11/10)

The invention discloses 2 -trifluoromethyl -4 - amino - quinoline derivatives and application thereof, and comprises a compound represented by the following general formula I. The prepared compound is used for preparing an anti-tumor active drug, has a go

Design, Synthesis, and Antifungal Evaluation of Novel Quinoline Derivatives Inspired from Natural Quinine Alkaloids

Yang, Guan-Zhou,Zhu, Jia-Kai,Yin, Xiao-Dan,Yan, Yin-Fang,Wang, Yu-Ling,Shang, Xiao-Fei,Liu, Ying-Qian,Zhao, Zhong-Min,Peng, Jing-Wen,Liu, Hua

, p. 11340 - 11353 (2019/10/14)

Inspired by quinine and its analogues, we designed, synthesized, and evaluated two series of quinoline small molecular compounds (a and 2a) and six series of quinoline derivatives (3a-f) for their antifungal activities. The results showed that compounds 3e and 3f series exhibited significant fungicidal activities. Significantly, compounds 3f-4 (EC50 = 0.41 μg/mL) and 3f-28 (EC50 = 0.55 μg/mL) displayed the superior in vitro fungicidal activity and the potent in vivo curative effect against Sclerotinia sclerotiorum. Preliminary mechanism studies showed that compounds 3f-4 and 3f-28 could cause changes in the cell membrane permeability, accumulation of reactive oxygen species, loss of mitochondrial membrane potential, and effective inhibition of germination and formation of S. sclerotiorum sclerotia. These results indicate that compounds 3f-4 and 3f-28 are novel potential fungicidal candidates against S. sclerotiorum derived from natural products.

Searching for New Leads for Tuberculosis: Design, Synthesis, and Biological Evaluation of Novel 2-Quinolin-4-yloxyacetamides

Pitta, Eleni,Rogacki, Maciej K.,Balabon, Olga,Huss, Sophie,Cunningham, Fraser,Lopez-Roman, Eva Maria,Joossens, Jurgen,Augustyns, Koen,Ballell, Lluis,Bates, Robert H.,Van Der Veken, Pieter

supporting information, p. 6709 - 6728 (2016/08/05)

In this study, a new series of more than 60 quinoline derivatives has been synthesized and evaluated against Mycobacterium tuberculosis (H37Rv). Apart from the SAR exploration around the initial hits, the optimization process focused on the improvement of the physicochemical properties, cytotoxicity, and metabolic stability of the series. The best compounds obtained exhibited MIC values in the low micromolar range, excellent intracellular antimycobacterial activity, and an improved physicochemical profile without cytotoxic effects. Further investigation revealed that the amide bond was the source for the poor blood stability observed, while some of the compounds exhibited hERG affinity. Compound 83 which contains a benzoxazole ring instead of the amide group was found to be a good alternative, with good blood stability and no hERG affinity, providing new opportunities for the series. Overall, the obtained results suggest that further optimization of solubility and microsomal stability of the series could provide a strong lead for a new anti-TB drug development program.

THIAZOLIDINE DERIVATIVE AND MEDICINAL USE THEREOF

-

Page 39, (2010/02/07)

A thiazolidine derivative represented by the formula (I) wherein each symbol is as defined in the specification, and a pharmaceutically acceptable salt thereof exhibit a potent DPP-IV inhibitory activity, and can be provided as an agent for the prophylaxis or treatment of diabetes, an agent for the prophylaxis or treatment of obesity and the like.

PROLINE DERIVATIVES AND USE THEREOF AS DRUGS

-

, (2008/06/13)

The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

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