39178-35-3

Usage

Uses

Used in Pharmaceutical Industry:
ISONICOTINOYL CHLORIDE HYDROCHLORIDE is used as a key intermediate for the synthesis of pharmaceutical compounds. Its application is particularly significant in the development of Tetrahydropyrroloquinolinone type dual inhibitors of Aromatase/Aldosterone Synthase. These inhibitors represent a novel therapeutic approach for breast cancer patients who are at risk of cardiovascular diseases, offering a promising avenue for treatment.
Used in Chemical Synthesis:
In the field of chemical synthesis, ISONICOTINOYL CHLORIDE HYDROCHLORIDE serves as a valuable building block for creating complex organic molecules. It has been specifically used in the synthesis of 7,16-diisonicotinoyltetraaza[14]annulene, showcasing its versatility and importance in the development of novel chemical structures with potential applications in various industries.

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

Upstream product

• 14254-57-0 4-(chlorocarbonyl)pyridine 
• 37832-54-5 4-piperidinecarboxylic acid hydrochloride 
• 55-22-1 pyridine-4-carboxylic acid 

Downstream Products

• 64479-78-3 N-(pyrid-4-yl)isonicotinamide 
• 101284-82-6 1-isonicotinoyl-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazole 
• 1570-45-2 isonicotinic acid ethylester 
• 100871-55-4 isonicotinic acid-(3,4-dichloro-phenethylamide) 
• 109408-34-6 N'-(N-benzoylglycinyl)isonicotinic hydrazide 
• 68279-83-4 isonicotinic acid-(4-acetyl-anilide) 
• 717857-25-5 N-(biphenyl-2-yl)iso-nicotinamide 
• 99969-94-5 thioisonicotinic acid S-phenyl ester 
• 6631-22-7 N,N′-bis(4-pyridinecarboxamide)-1,2-ethane 
• 77924-05-1 N,N-Diisopropyl-4-pyridinecarboxamide 
• 14548-48-2 4-(4-chlorobenzoyl)pyridine 
• 37128-60-2 4-Pyridyl 3-(2-ethyl)indolyl ketone 
• 112981-39-2 diphenylmethyl isonicotinate 
• 90541-90-5 C₂₉H₂₅N₃O₆ 

Relevant academic research and scientific papers

Iron and Manganese Complexes of 2-Carbonyl Pyrrolyls: Scorpionate Sandwich Anions and Extended Structures

Attempts to synthesize complexes of Fe and Mn(II) with 2-amidopyrrolyl ligands (N-O) were unsuccessful, and only small amounts of the trivalent tris complexes M(N-O)3 were detected, although unusually in the case of Fe(III) a fac structure is observed. In contrast the 2-benzoylpyrrolyl systems give M(II) complexes, and in all instances thus far where Na+ is present, a scorpionate fac-[MII(N-O)3]- unit self-assembles into sandwich anions [MII(N-O)3Na(O-N)3MII]- in which the central metal is efficiently encapsulated by interdigitation of the aryl units. Extended structures are readily made through the use of a 2-(4-pyridinoyl)pyrrolylamide ligand. When Li+ is used, the scorpionate ligand is not assembled, and instead [M(N-O)2] units give rhombic 2D grids. The Fe system displays spin-crossover at 120 K. (Figure Presented).

Multi-arm ionic liquid crystals formed by pyridine-mesophase and copper phthalocyanine

Phthalocyanine emerged as a promising molecular component for photoreceptors because of their high extinction coefficients, stability, and energy band gaps well-matched to the incident solar spectrum. The cavity in the center can be occupied by dozens of cation types to form metallo-phthalocyanines which show a number of special properties such as electrical, optical, non-linear optical and opto-electronic. A kind of novel multi-arm ionic liquid crystalline materials combined the characteristics of liquid crystals with phthalocyanine were prepared using copper phthalocyanine as a matrix, [1,1′-biphenyl]-4,4′-diyl diisonicotinate or cyclohexane-1,4-diyl diisonicotinate as a mesogen, and different ions (B-SO3 ?, C-SO3 ?, H2PO4 ? and BF4 ?) as counterions. The mesomorphic properties of these ionic liquid crystals were investigated by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction measurements. The copper phthalocyanine-based multi-arm ionic liquid crystals showed excellent electrical conductivity (the optimum value of conductivity can reach 0.0248 S/cm) because of their ionic channels and π-π stacking structure. This materials might provide a promising application prospect for electronic or optoelectronic applications.

Synthesis and the crystal structures of N-(2-nitroxyethyl)isonicotinamide and its complexes with PdCl2 and PtCl2 as potential antitumor medicines

Previously unknown N-(2-nitroxyethyl)isonicotinamide was synthesized by the reaction of isonicotinoyl chloride with 2-nitroxyethylamine and was used as a ligand in the reactions with PdCl2 and PtCl2 to prepare new complexes, viz., trans-bis[(2-nitroxyethyl)isonicotinamide-N]dichloropalladium(11) and ci.s-bis[(2-nitroxyethyl)isonicotinamide-N]dichloroplatinum(11), respectively. The structures of the ligand and the resulting complexes were established by X-ray diffraction analysis.

Synthesis and antimicrobial characteristics of novel biocides, 4,4'- (1,6-hexamethylenedioxydicarbonyl)bis(1-alkylpyridinium iodide)s

Potent new biocides against both bacteria and fungi, 4,4'-(1,6- hexamethylenedioxydicarbonyl)bis(1-alkylpyridinium iodide)s (4DOCBP-6,n) (alkyl chain length, n=8, 10, 12, 14, 16 and 18) were synthesized. 4DOCBP- 6,n is a bis-quaternary ammonium compound (bis-QAC) and has a symmetrical dimeric structure which is composed of two alkylpyridinium iodides connected with a hexamethylenedioxydicarbonyl chain. 4DOCBP-6,10 and 4DOCBP-6,12 exhibited wide and effective antimicrobial spectra, compared with those of typical bactericides, N-dodecylpyridinium iodides (P-12) and benzyldimethyldodecylammonium chloride (BAC), or a popularly-used fungicide, 2-(4-thiazolyl)benzimidazole (TBZ). Their superior properties would be due to the unique dimeric structure which contains two active moieties in a molecule.

Direct electrochemistry of cytochrome c at modified Si(100) electrodes

This paper demonstrates the direct electron transfer between the heme moiety of horse hearth cytochrome c and a pyridinyl group on self-assembled-monolayer-modified Si(100) electrodes. Self-assembled monolayers (SAMs) containing the putative receptor ligand were prepared by a step-wise procedure using "click" reactions of acetylene-terminated alkyl monolayers and isonicotinic acid azide derivatives. Unoxidized Si(100) electrodes, possessing either isonicotinate or isonicotinamide receptor ligands, were characterized using X-ray photoelectron spectroscopy, contact-angle goniometry, cyclic voltammetry, and electrochemical impedance spectroscopy. The ability of isonicotinic acid terminated layers to coordinatively bind the redox center of cytochrome c was found to be restricted to pyridinyl assemblies with a paraester linkage present. The protocol detailed here offers an experimentally simple modular approach to producing chemically well-defined SAMs on silicon surfaces for direct electrochemistry of a well-studied model redox protein.

Novel photo-polymerizable chiral hydrogen-bonded self-assembled complexes: Preparation, characterization and the utilization as a thermal switching reflective color film

In this study, novel photopolymerizable chiral hydrogen-bonded self-assembled complexes (PCHSCs) were fabricated, which were derived from photopolymerizable 4-(6-acryloyloxyhexyloxy) benzoic acid (AHBA, proton donor) and chiral pyridine derivatives (proton acceptor). Their structures were characterized by fourier transform infrared (FT-IR) and the proton nuclear magnetic resonance (1H-NMR) spectoscopy. The thermal stability, phase behaviors and helical twisted power (HTP) characteristics of the PCHSC were investigated by measuring the variable-temperature FT-IR spectrum, differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and the Cano wedge. The results demonstrate that all the PCHSCs have good thermal stability within a temperature range, and the pitch length of all the cells containing the PCHSCs increases with increasing temperature, which is due to the fact that the HTP values of all the PCHSCs decrease with an increase of temperature. What's more, the introduction of AHBA leads to chiral enhancement of the PCHSCs. Based on the above results, a polymer stabilized cholesteric liquid crystals (PSCLCs) composite with the above PCHSCs was prepared and the thermal-optical characteristics of the PSCLCs film were investigated. The results confirm that the reflective wavelength of the PSCLCs film before and after irradiation can be thermally switched to reflect green and red color from the initial state reflecting a blue/green color with the temperature increasing from 30 °C to 75 °C. On the basis of this mechanism, the novel material in this study can be used as optical/photonic paper, optical sensors and LCs displays, etc.

Tuning gel state properties of supramolecular gels by functional group modification

The factors affecting the self-assembly process in low molecular weight gelators (LMWGs) were investigated by tuning the gelation properties of a well-known gelator N-(4-pyridyl)isonicotinamide (4PINA). The N—H···N interactions responsible for gel formation in 4PINA were disrupted by altering the functional groups of 4PINA, which was achieved by modifying pyridyl moieties of the gelator to pyridyl N-oxides. We synthesized two mono-N-oxides (INO and PNO) and a di-N-oxide (diNO) and the gelation studies revealed selective gelation of diNO in water, but the two mono-N-oxides formed crystals. The mechanical strength and thermal stabilities of the gelators were evaluated by rheology and transition temperature (Tgel) experiments, respectively, and the analysis of the gel strength indicated that diNO formed weak gels compared to 4PINA. The SEM image of diNO xerogels showed fibrous microcrystalline networks compared to the efficient fibrous morphology in 4PINA. Single-crystal X-ray analysis of diNO gelator revealed that a hydrogen-bonded dimer interacts with adjacent dimers via C—H···O interactions. The non-gelator with similar dimers interacted via C—H···N interaction, which indicates the importance of specific non-bonding interactions in the formation of the gel network. The solvated forms of mono-N-oxides support the fact that these compounds prefer crystalline state rather than gelation due to the increased hydrophilic interactions. The reduced gelation ability (minimum gel concentration (MGC)) and thermal strength of diNO may be attributed to the weak intermolecular C—H···O interaction compared to the strong and unidirectional N—H···N interactions in 4PINA.

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.

Design, synthesis and biological evaluation of N-(4-alkoxy-3-cyanophenyl)isonicotinamide/nicotinamide derivatives as novel xanthine oxidase inhibitors

A series of N-(4-alkoxy-3-cyanophenyl)isonicotinamide/nicotinamide derivatives was designed, synthesized and evaluated for inhibitory potency in vitro against xanthine oxidase. The isonicotinamide series was considerably more effective than the nicotinamide series. SARs analysis revealed that the isonicotinoyl moiety played a significant role on the inhibition and that a benzyl ether tail (e.g., ortho-cyanobenzoxy) linked to the benzonitrile moiety benefits the inhibitory potency. Among these compounds, 10q (IC50 = 0.3 μM) was identified to be the most potent in this work and was observed to be 28.3-fold more potent than allopurinol but 20-fold less potent than topiroxostat. The Lineweaver-Burk plot showed that 10q acted as a mixed-type inhibitor on xanthine oxidase. Molecular modeling provided a reasonable explanation for the SARs observed in this study.

Binuclear dichlorido(η6-p-cymene)ruthenium(II) complexes with bis(nicotinate)- And bis (isonicotinate)-polyethylene glycol ester ligands

Neutral binuclear ruthenium complexes 1-8 of the general formula [{RuCl2(η6-p-cym)}2 μ-(N∩N)] (N∩N=bis(nicotinate)- and bis (isonicotinate)-polyethylene glycol esters: (3-py)COO(CH2CH2O)nCO(3-py) and (4-py)COO(CH2CH2O)nCO(4-py), n =1-4), as well as mononuclear [RuCl2(η6-p-cym)((3-py)COO(CH2CH2OCH3)-κN)], complex 9, were synthesized and characterized using elemental analysis and electrospray ionization high-resolution mass spectrometry, infrared, 1H NMR and 13C NMR spectroscopies. Stability of the binuclear complexes in the presence of dimethylsulfoxide was studied. Furthermore, formation of a cationic complex containing bridging pyridine-based bidentate ligand was monitored using 1H NMR spectroscopy. Ligand precursors, polyethylene glycol esters of nicotinic (L1·2HCl-L4·2HCl and L9·HCl) and isonicotinic acid dihydrochlorides (L5·2HCl-L8·2HCl), binuclear ruthenium(II) complexes 1-8 and mononuclear complex 9 were tested for in vitro cytotoxicity against 518A2 (melanoma), 8505C (anaplastic thyroid cancer), A253 (head and neck tumour), MCF-7 (breast tumour) and SW480 (colon carcinoma) cell lines.