13160-62-8

Upstream product

• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 100-01-6 4-nitro-aniline 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 59-67-6 nicotinic acid 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 

Downstream Products

• 19060-64-1 N-(4-aminophenyl)-3-pyridinecarboxamide 

Relevant academic research and scientific papers

A Convenient One-Pot Synthesis and Nematicidal Activity of Nicotinic Acid Amides

Seven nicotinic acid amides were synthesized by condensation of nicotinic acid adsorbed on silica gel with different aromatic amines. The synthesized compounds were characterized by 1H and 13C NMR and IR spectroscopy and screened for their nematicidal activity against root knot nematode Meloidogyne incognita by egg hatching and mortality test. All compounds exhibited significant nematicidal potential as compared to control. Maximum egg hatching inhibition potential was exhibited by N-(4-bromophenyl)nicotinamide while N-(2,4,5-trichlorophenyl)nicotinamide showed the maximum mortality potential.

Catalytic hydrogenation of: N -4-nitrophenyl nicotinamide in a micro-packed bed reactor

Recent advancements in micro-flow technologies and a drive toward more efficient, greener and safer processes have led to a renaissance in flow-chemistry for pharmaceutical production. In this work, we demonstrate the use of a stabilized Pd nanoparticle-organic-silica catalyst to selectively catalyze the hydrogenation of N-4-nitrophenyl nicotinamide, a functionalized active pharmaceutical ingredient (API) surrogate. Extensive catalyst and reactor characterization is provided to establish an in-depth understanding of the unique multiphase dynamics within the micro-packed bed reactor, including the identification of a large liquid holdup (74-84%), rapid multiphase mass transfer (kma > 1 s-1), and liquid residence time distributions. A kinetic analysis has revealed that the surface catalyzed hydrogenation progresses through a condensation mechanism whereby an azo dimer intermediate is formed and rapidly consumed. Finally, a parametric study was performed at various pressures, temperatures, residence times and flow regimes to achieve quantitative chemoselective conversion of the nitroarene to the corresponding primary amine.

Diarylurea histone deacetylation enzyme inhibitor

The invention belongs to the field of medical chemistry and particularly relates to a diarylurea histone deacetylation enzyme inhibitor, a medicine composition containing the histone deacetylation enzyme inhibitor, application of the inhibitor to preparat

Synthesis and biological evaluation of 1-(2-aminophenyl)-3-arylurea derivatives as potential EphA2 and HDAC dual inhibitors

A series of 1-(2-aminophenyl)-3-arylurea novel derivatives were synthesized and evaluated against Ephrin type-A receptor 2 (EphA2) and histone deacetylases (HDACs) kinase. Most of the compounds exhibited inhibitory activity against EphA2 and HDAC. The antiproliferative activities were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) (thiazolyl blue, tetrazolium blue) against the human cancer cell lines HCT116, K562 and MCF7. Compounds 5a and b showed the most potent inhibitory activity against EphA2 and HDAC. However, compound 5b exhibited higher potency against HCT116 (IC50=5.29 μM) and MCF7 (IC50=7.42 μM). 1-(2-Aminophenyl)-3-arylurea analogues may serve as new EphA2-HDAC dual inhibitors.

Design, synthesis, and biological activity of urea derivatives as anaplastic lymphoma kinase inhibitors

In anaplastic large-cell lymphomas, chromosomal translocations involving the kinase domain of anaplastic lymphoma kinase (ALK), generally fused to the 5' part of the nucleophosmin gene, produce highly oncogenic ALK fusion proteins that deregulate cell cycle, apoptosis, and differentiation in these cells. Other fusion oncoproteins involving ALK, such as echinoderm microtubule-associated protein-like 4-ALK, were recently found in patients with non-small-cell lung, breast, and colorectal cancers. Recent research has focused on the development of inhibitors for targeted therapy of these ALK-positive tumors. Because kinase inhibitors that target the inactive conformation are thought to be more specific than ATP-targeted inhibitors, we investigated the possibility of using two known inhibitors, doramapimod and sorafenib, which target inactive kinases, to design new urea derivatives as ALK inhibitors. We generated a homology model of ALK in its inactive conformation complexed with doramapimod or sorafenib in its active site. The results elucidated why doramapimod is a weak inhibitor and why sorafenib does not inhibit ALK. Virtual screening of commercially available compounds using the homology model of ALK yielded candidate inhibitors, which were tested using biochemical assays. Herein we present the design, synthesis, biological activity, and structure-activity relationships of a novel series of urea compounds as potent ALK inhibitors. Some compounds showed inhibition of purified ALK in the high nanomolar range and selective antiproliferative activity on ALK-positive cells.

AN UNUSUAL SYNTHESIS OF NICOTINAMIDES

Reaction of 2,3-pyridinedicarboxylic anhydride (1) with a substituted aniline (2) in acetic acid gave rise to a mixture of two products.These two products were identified as the cyclic imide (4) and nicotinamide (5).A mechanistic scheme consistent with empirical observations is proposed.

POLAROGRAPHIC REDUCTION OF 1-BENZYL-N-(p-X-PHENYL)-3-AMINOCARBONYLPYRIDINIUM SALTS

The substitution effect of different groups X (N(CH2CH3)2, OH, OCH3, CH3, NHCOCH3, H, Cl, COOCH2CH3 and NO2) on the polarographic behaviour of 3-(N-p-X-phenylaminocarbonyl)pyridines (I),1-benzyl-N-(p-X-phenyl)-3-aminocarbonylpyridinium cations (II) and their respective 1,4-dihydroderivatives (III) has been investigated in anhydrous solution of dimethylformamide with 0.1 mol 1-1 (n-C4H9)4N+PF6- as supporting electrolyte.The half-wave potentials of the reduction wave of I and II, which correspond to the uptake of a single electron (wave B) and to the formation of a primary radical, obey a Hammett correlation in a similar way as it is in the case of 1-benzyl- and 1-phenyl-3-amino-carbonylopyridinium cations substituted at carbon 4 on the benzene nucleus.The slope q?,R in the Hammett plot equals 0.192 V (I) and 0.104 V (II) for anhydrous DMF and compares thus with this slope obtained with the 1-benzyl- and 1-phenyl derivatives in our previous communications.