39178-35-3Relevant articles and documents
Iron and Manganese Complexes of 2-Carbonyl Pyrrolyls: Scorpionate Sandwich Anions and Extended Structures
Li, Lihong,Clarkson, Guy J.,Lees, Martin R.,Howson, Suzanne E.,Tan, Sze-Yin,Turner, Scott S.,Scott, Peter
, p. 2543 - 2549 (2015)
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).
Synthesis and the crystal structures of N-(2-nitroxyethyl)isonicotinamide and its complexes with PdCl2 and PtCl2 as potential antitumor medicines
Fedorov,Golovina,Fadeev,Strukov,Kedrov,Shilov,Boiko,Atovmyan
, p. 520 - 524 (2001)
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.
Direct electrochemistry of cytochrome c at modified Si(100) electrodes
Ciampi, Simone,Gooding, J. Justin
, p. 5961 - 5968 (2010)
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.
Tuning gel state properties of supramolecular gels by functional group modification
Ghosh, Dipankar,Mulvee, Matthew T.,Damodaran, Krishna K.
, (2019/10/02)
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.
Design, synthesis and biological evaluation of N-(4-alkoxy-3-cyanophenyl)isonicotinamide/nicotinamide derivatives as novel xanthine oxidase inhibitors
Zhang, Ting-jian,Li, Song-ye,Wang, Lin,Sun, Qi,Wu, Qing-xia,Zhang, Yi,Meng, Fan-hao
, p. 362 - 372 (2017/10/16)
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.
