20260-53-1

Usage

Uses

Used in Pharmaceutical Industry:
Nicotinoyl chloride hydrochloride is used as a key intermediate for the preparation of cardiovascular agents and renal drugs. Its nicotinic acid analog nature allows for the development of medications that can address a range of health issues related to the heart and kidneys.
Used in Chemical Synthesis:
Nicotinoyl chloride hydrochloride is used as a reagent in the preparation of various complex organic compounds, such as 1-[5-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-3-O-(3-pyridylcarbonyl)-β-D-ribofuranosyl]uracil, bis(ethylenedithio)tetrathiafulvalene derivatives, and 7,16-dinicotinoylated or 7,16-diisonicotinoylated compounds via reaction with tetraaza[14]annulene and its complexes. These compounds have potential applications in various fields, including pharmaceuticals, materials science, and chemical research.
Overall, nicotinoyl chloride hydrochloride plays a crucial role in the development and synthesis of a wide range of pharmaceuticals and organic compounds, making it an essential component in the chemical and pharmaceutical industries.

InChI:InChI=1/C6H4ClNO.ClH/c7-6(9)5-2-1-3-8-4-5;/h1-4H;1H

Upstream product

• 59-67-6 nicotinic acid 
• 636-79-3 nicotinic acid hydrochloride 

Downstream Products

• 77727-88-9 (pyridin-3-yl)(pyrrolidin-1-yl)methanone 
• 7681-15-4 n-propyl nicotinate 
• 21937-63-3 N,N-Dimethylaminoethyl nicotinate 
• 5868-05-3 niceritrol 
• 70136-02-6 octyl nicotinate 
• 50917-69-6 nicotinic acid isopentyl ester 
• 49558-04-5 Nicotinsaeure-pentylester 
• 19416-51-4 ethylene glycol monomethyl ether nicotinate 
• 5338-17-0 Nicotinsaeure-decylester 
• 66170-39-6 hexadecyl nicotinate 
• 71653-43-5 2-phenylethyl nicotinate 
• 6556-11-2 inositol hexanicotinate 
• 533-07-3 nicotinic acid-(2-hydroxy-3-o-tolyloxy-propyl ester) 
• 132567-49-8 nicotinic acid-(4-chloro-2-isopropyl-5-methyl-phenyl ester) 

Relevant academic research and scientific papers

Self-assembled mononuclear palladium(II) based molecular loops

The meta-pyridine appended bidentate ligands L1, L2 and L3, crafted with flexible polyether spacer, are prepared by condensation of nicotinoyl chloride hydrochloride with di, tri-, and tetra-ethylene glycol, respectively. Self-assembled palladium(II) based mononuclear molecular loops of general formula cis-[Pd(N-N)(L)](NO 3)2 are obtained exclusively by combining 1 equiv. of a ligand L with 1 equiv. of a cis-protected palladium(II) component, cis-[Pd(N-N)(NO3)2]. Complexation of 2 equiv. of L with 1 equiv. of palladium(II) nitrate also resulted mononuclear complexes, i.e. [Pd(L)2](NO3)2. The ligands used in the complexation reactions are L1, L2 and L3 where as the cis-protecting units N-N employed are ethylenediamine (en), 2,2′-bipyridine (bpy), and 1,10-phenanthroline (phen). Thus 12 number of mononuclear complexes are prepared using all possible combination of above mentioned three number of ligands and four variety of palladium(II) components. Large chelate rings are realized irrespective of the spacer length or type of palladium(II) component used. All the resulted compounds are characterized by NMR and ESI-MS techniques and the structure of cis-[Pd(en)(L1)] (NO3)2, cis-[Pd(bpy)(L1)](NO3) 2 and [Pd(L3)2](NO3)2 are confirmed by single crystal X-ray diffraction. The binding abilities of cis-[Pd(phen)(L1)](NO3)2, cis-[Pd(phen)(L 2)](NO3)2 and cis-[Pd(phen)(L 3)](NO3)2 with DNA has been investigated by ethidium bromide displacement assay and gel electrophoresis.

Asymmetric synthesis of tetracyclic substructures of Strychnos indole alkaloids

The addition of the enolate of methyl 1-methyl-2-indoleacetate 1 and lithium 2-(lithiomethyl)indole-1-carboxylate 5 to pyridines and N-alkylpyridinium salts bearing a chiral auxiliary at the 3-position (tolylsulfinyl, acyl iron complexes, bornane-10,2-sultam), with subsequent acid cyclization of the resulting dihydropyridines, is investigated.

Synthesis and pharmacological evaluation of novel selective MOR agonist 6β-pyridinyl amidomorphines exhibiting long-lasting antinociception

It was previously reported that 6β-aminomorphinan derivatives show high affinity for opiate receptors. Novel 6β-heteroarylamidomorphinanes were designed based on the MOR selective antagonist NAP. The 6β-aminomorphinanes were prepared by stereoselective Mitsunobu reaction and subsequently acylated with nicotinic acid and isonicotinic acid chloride hydrochlorides. The receptor binding and efficacy were determined in vitro and the analgesic activity was studied in vivo. The in vitro studies revealed moderate selectivity for the MOR. At least two compounds in this series exhibited a long-lasting analgesic response when administered subcutaneously and intracerebroventricularly. When the substances were given intracerebroventricularly to mice, they showed analgesic potency comparable to morphine.

Homochiral crystallization of helical coordination chains bridged by achiral ligands: Can it be controlled by the ligand structure?

Homochiral/heterochiral crystallizations of helical chiral polymer chains bridged by achiral poly-pyridyl ligands dependent on the structures of the bridging ligands and independent on the solvent are described, implying a possible strategy to design achiral crystals of helical chains using chiral bridging ligands.

Synthesis of Conjugates of hyaluronic and nicotinic acids

Conjugates with nicotinic acid of hyaluronic acid carboxylic and hydroxyl groups were synthesized and exhibited polyampholyte properties.

Unusual adsorption behaviours and responsive structural dynamics: Via selective gate effects of an hourglass porous metal-organic framework

An hourglass porous metal-organic framework, LIFM-12, constructed on a T-shaped flexible ligand with Cu2+ paddle-wheel clusters, shows temperature and gas adsorption responsive structural dynamics upon reversible molecular guest binding. Temperature-dependent single crystal and powder X-ray diffraction experiments show that the open gate status of the framework with adaptive behaviours facilitates kinetic diffusion of gas molecules resulting in the sequential filling of pores of different sizes, thus creating a breathing behaviour reminiscent of the observation of several steps in adsorption isotherms. In addition, adsorption studies revealed that LIFM-12 performs exceptional adsorption selectivity of 10-25 for CO2versus light gases N2, CH4, and CO and up to 200 for C3H6versus CH4.

N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesizecis-enamides through vinyl benziodoxolones

The stereoselective synthesis ofcis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) fromO-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature. The reaction tolerated variousO-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuteratedcis-β-N-MeO-amide-VBXs were also synthesized using deuterium oxide as the deuterium source. Valine-derivedcis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derivedcis-enamides without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.

ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE 1 (ENPP-1) INHIBITORS AND USES THEREOF

Disclosed herein are methods and compounds of augmenting and enhancing the production of type I IFNs in vivo. In some embodiments, the compounds disclosed herein are ENPP-1 inhibitors, pharmaceutical compositions, and methods for the treatment of cancer or a viral infection.

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.

Synthesis and Quantitative Structure-activity Relationships Study for Arylpropenamide Derivatives as Inhibitors of Hepatitis B Virus Replication

A series of new arylpropenamide derivatives containing different aryl groups were synthesized, characterized, and evaluated for their anti-hepatitis B virus (HBV) activities. A new high accuracy QSAR model of arylpropenamide was constructed based on a more completely activities data and calculation parameter. The 2D-QSAR equations, by using DFT and multiple linear regression analysis methods, revealed that higher value of thermal energy (TE) and lower entropy (S?) increase the anti-HBV activities of the arylpropenamide molecules. Predictive 3D-QSAR models were established by SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction.