60172-08-9

Upstream product

• 72109-70-7 4-(2-phenylhydrazin)pyridine 
• 586-78-7 para-nitrophenyl bromide 
• 22752-98-3 N-(4-pyridyl)pyridinium hydrochloride 
• 504-24-5 4-aminopyridine 
• 25551-60-4 N-(4-nitrophenyl)-4-pyridinamine 

Downstream Products

• 23552-71-8 C₁₈H₁₄N₄O₃ 
• 1332220-29-7 4-tert-butyl-N-[[4-(4-pyridylamino)phenyl]-carbamothioyl]benzamide hydrochloride 
• 1020086-91-2 C₁₉H₁₇N₄O₃⁽¹⁺⁾*Cl^(1-) 
• 1020086-93-4 1-methyl-4-{4-[(4-nitroanilino)carbonyl]anilino}pyridinium tosylate 
• 50440-30-7 4-[(6-nitroquinolin-4-yl)amino]-N-[4-(pyridin-4-ylamino)phenyl]benzamide 
• 23625-78-7 4-[p-(4-pyridylamino)phenylcarbamoyl]aniline 

Relevant academic research and scientific papers

AKT3 MODULATORS

Compounds of Formula Ia, lb, or Ic, Formula (Ia); Formula (Ib); or Formula (Ic), are described, where the various substituents are defined herein. The compounds can modulate a property or effect of Akt3 in vitro or in vivo, and can also be used, individually or in combination with other agents, in the prevention or treatment of a variety of conditions. Methods for synthesizing the compounds are described. Pharmaceutical compositions and methods of using these compounds or compositions, individually or in combination with other agents or compositions, in the prevention or treatment of a variety of conditions are also described.

Structure-activity relationships for 4-anilinoquinoline derivatives as inhibitors of the DNA methyltransferase enzyme DNMT1

A series of 4-anilinoquinoline derivatives related to the known inhibitor SGI-1027, containing side chains of varying pKa, were prepared by acid-catalysed coupling of the pre-formed side chains with 4-chloroquinolines. The compounds were evaluated for their ability to reduce the level of DNMT1 protein in HCT116 human colon carcinoma cells by Western blotting. With a very strongly basic N-methylpyridinium side chain, only NHCO-linked compounds were effective, whereas less strongly basic ((diaminomethylene)hydrazono)ethyl or 3-methylpyrimidine-2,4-diamine side chains allowed both NHCO- and CONH-linked compounds to show activity. In contrast, the pKa of the quinoline unit had little apparent influence on activity.

SAR analysis of a series of acylthiourea derivatives possessing broad-spectrum antiviral activity

A series of acylthiourea derivatives were designed, synthesized, and evaluated for broad-spectrum antiviral activity with selected viruses from Poxviridae (vaccinia virus) and two different genera of the family Bunyaviridae (Rift Valley fever and La Cross

QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION

Quinoline derivatives, particularly 4-anilinoquinoline derivatives, are provided. Such quinoline derivatives can be used for modulation of DNA methylation, such as effective inhibition of methylation of cytosine at the C-5 position, for example via selective inhibition of DNA methyltransferase DNMT1. Methods for synthesizing numerous 4-anilinoquinoline derivatives and for modulating DNA methylation are provided. Also provided are methods for formulating and administering these compounds or compositions to treat conditions such as cancer and hematological disorders.

Acid-catalysed disproportionation and benzidine rearrangement of phenylhydrazinopyridines: Reaction pathways, kinetics and mechanism

A kinetic and product analysis study of the reaction of 4-[N′-(4-hydroxyphenylhydrazino)]pyridine (1) and 4-(N′-phenylhydrazino)pyridine (2) in 10-55 wt% aqueous sulfuric acid media is reported. The final products obtained from 1 are the oxidation product, 4-(4-hydroxyphenylazo)pyridine (3), and the two reduction products 4-aminophenol and 4-aminopyridine. This product pattern resembles that of the disproportionation products observed in some cases of the benzidine rearrangement. The reaction of 2 gives a complex product mixture including the disproportionation products 4-(phenylazo)pyridine (4), aniline and 4-aminopyridine, and other benzidine-type products including a p-semidine. Complicating the situation is the concurrent hydroxylation and disproportionation of 4 which take place in these media, giving 3, 4-aminopyridine and 4-aminophenol. The observed pseudo-first-order rate constants for the disproportionations increase steeply with acid concentration without showing any downturn at higher acidities. The disproportionation rate constants for 1 and 2 are much larger than those for the hydroxylation of 4. A reasonable mechanism which explains the observations is a benzidine-type rearrangement with accompanying disproportionation. To our knowledge this work is the first description of this type of reaction in substrates containing pyridinium rings.