2226517-76-4 Usage
Description
6-bromo-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine is a chemical compound characterized by its quinoline structure, which is substituted with a bromine atom at the 6th position and a trimethoxyphenyl group at the 4th position. 6-bromo-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine is known for its potential applications in various fields due to its unique chemical properties and interactions.
Uses
Used in Pharmaceutical Industry:
6-bromo-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine is used as a pharmaceutical compound for its potential therapeutic effects. The compound's unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 6-bromo-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine serves as a valuable compound for studying the properties and reactivity of quinoline derivatives. Its unique substitution pattern can provide insights into the synthesis and modification of related compounds.
Used in Material Science:
6-bromo-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine may also find applications in material science, particularly in the development of new materials with specific optical, electronic, or magnetic properties. The compound's structure and functional groups can be exploited to create novel materials with tailored characteristics.
Used in Drug Delivery Systems:
Similar to gallotannin, 6-bromo-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine could be employed in drug delivery systems to enhance its bioavailability and therapeutic outcomes. By incorporating the compound into various carriers, such as organic or metallic nanoparticles, its delivery and efficacy against specific targets can be improved.
Biochem/physiol Actions
SGC-GAK-1 (CA93) is an ATP-competitive cyclin G-associated kinase (GAK) inhibitor (Ki = 3.1 nM by ATP site fluorescent tracer displacement assay; KD = 4.5 nM by ITC) that effectively inhibits Dengue viral entry and packaging in cultures (IC50 = 920 nM) without detectable cytotoxicity. SGC-GAK-1 exhibits much reduced affinity toward only 4 other kinases among a panel of ～400 (KD = 1.9 nM/GAK vs. 110 nM/RIPK2, 190 nM/ADCK3, 520 nM/NLK, 980 nM/AVCR1 by ligand competitive binding assay; IC50 = 110 nM/GAK vs. 360 nM/RIPK2 by cellular target engagement assay). SGC-GAK-1N (CA71) is a structure analog and the recommended negative control (GAK KD = 7.1 μM by ligand competitive binding assay; GAK & RIPK2 IC50 >50 μM by cellular target engagement assay). For characterization details of SGC-GAK-1, please visit the SGC-GAK-1 probe summary on the Structural Genomics Consortium (SGC) website.SGC-GAK-1N is the negative control for the active probe, SGC-GAK-1. SGC-GAK-1N is available from Sigma. To learn more about and purchase SGC-GAK-1N, click here.To learn about other SGC chemical probes, visit sigma.com/sgc
References
1) Asquith?et al.?(2019),?SGC-GAK-1: A Chemical Probe for Cyclin G Associated Kinase (GAK); J. Med. Chem.,?62?2830
Check Digit Verification of cas no
The CAS Registry Mumber 2226517-76-4 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 2,2,2,6,5,1 and 7 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2226517-76:
(9*2)+(8*2)+(7*2)+(6*6)+(5*5)+(4*1)+(3*7)+(2*7)+(1*6)=154
154 % 10 = 4
So 2226517-76-4 is a valid CAS Registry Number.
2226517-76-4Relevant articles and documents
SGC-GAK-1: A Chemical Probe for Cyclin G Associated Kinase (GAK)
Asquith, Christopher R. M.,Berger, Benedict-Tilman,Wan, Jing,Bennett, James M.,Capuzzi, Stephen J.,Crona, Daniel J.,Drewry, David H.,East, Michael P.,Elkins, Jonathan M.,Fedorov, Oleg,Godoi, Paulo H.,Hunter, Debra M.,Knapp, Stefan,Müller, Susanne,Torrice, Chad D.,Wells, Carrow I.,Earp, H. Shelton,Willson, Timothy M.,Zuercher, William J.
, p. 2830 - 2836 (2019)
We describe SGC-GAK-1 (11), a potent, selective, and cell-active inhibitor of cyclin G-associated kinase (GAK), together with a structurally related negative control SGC-GAK-1N (14). 11 was highly selective in an in vitro kinome-wide screen, but cellular
Potent antiviral activity of novel multi-substituted 4-anilinoquin(az)olines
Saul, Sirle,Pu, Szu-Yuan,Zuercher, William J.,Einav, Shirit,Asquith, Christopher R.M.
, (2020/06/08)
Screening a series of 4-anilinoquinolines and 4-anilinoquinazolines enabled identification of potent novel inhibitors of dengue virus (DENV). Preparation of focused 4-anilinoquinoline/quinazoline scaffold arrays led to the identification of a series of high potency 6-substituted bromine and iodine derivatives. The most potent compound 6-iodo-4-((3,4,5-trimethoxyphenyl)amino)quinoline-3-carbonitrile (47) inhibited DENV infection with an EC50 = 79 nM. Crucially, these compounds showed very limited toxicity with CC50 values >10 μM in almost all cases. This new promising series provides an anchor point for further development to optimize compound properties.
Anti-tubercular activity of novel 4-anilinoquinolines and 4-anilinoquinazolines
Asquith, Christopher R.M.,Fleck, Neil,Torrice, Chad D.,Crona, Daniel J.,Grundner, Christoph,Zuercher, William J.
, p. 2695 - 2699 (2019/08/07)
We screened a series of 4-anilinoquinolines and 4-anilinoquinazolines and identified novel inhibitors of Mycobacterium tuberculosis (Mtb). The focused 4-anilinoquinoline/quinazoline scaffold arrays yielded compounds with high potency and the identification of 6,7-dimethoxy-N-(4-((4-methylbenzyl)oxy)phenyl)quinolin-4-amine (34) with an MIC90 value of 0.63–1.25 μM. We also defined a series of key structural features, including the benzyloxy aniline and the 6,7-dimethoxy quinoline ring, that are important for Mtb inhibition. Importantly the compounds showed very limited toxicity and scope for further improvement by iterative medicinal chemistry.
