41191-92-8Relevant academic research and scientific papers
Expedient Synthesis of Thioether-Functionalized Hydrotris(indazolyl)borate as an Anchoring Platform for Rotary Molecular Machines
Erbland, Guillaume,Gisbert, Yohan,Rapenne, Gwéna?l,Kammerer, Claire
, p. 4731 - 4739 (2018)
Major improvements in the synthesis of surface-mounted rotary molecular machines based on ruthenium(II) complexes are reported. The development of a one-pot indium(III)-mediated “N-deprotection/ester reductive sulfidation” sequence allowed step economy, reproducibility and high efficiency in the synthesis of the thioether-functionalized tripodal ligand. Switching to the thallium salt of hydrotris(indazolyl)borate and to microwave heating further optimized the preparation of the common intermediate in the modular synthesis of symmetric and dissymmetric molecular motors and gears. The penta(4-bromophenyl)cyclopentadienyl ruthenium(II) key precursor is now reproducibly synthesized in 5 steps and 31 % overall yield on the longest linear sequence. Subsequent fivefold Suzuki–Miyaura coupling with ferroceneboronic acid led to a new C5-symmetric pentaferrocenyl molecular motor.
Synthesis of new tripodal tri-functionalized hydrotris(indazol-1-yl)borate ligands and x-ray structures of their cyclopentadieneruthenium complexes
Carella, Alexandre,Vives, Guillaume,Cox, Tara,Jaud, Jo?l,Rapenne, Gwéna?l,Launay, Jean-Pierre
, p. 980 - 987 (2006)
Two new tripodal ligands designed to anchor complexes onto surfaces have been synthesized. They integrate ester or thioether functions at the 6-position of the indazoles. Potassium hydrotris[6-(ethoxycarbonyl)indazolyl]borate and potassium hydrotris{6-[(ethylsulfanyl)methyl]indazolyl}borate exhibit three pendant groups oriented to anchor complexes onto an oxide and a metallic surface, respectively. Their complexation with [RuCp(CH3CN) 3]PF6 yielded two piano-stool-shaped complexes that were characterized by X-ray diffraction. Comparison with the synthesized unfunctionalized analog showed that the three 6-substituted functions do not interfere with the coordination site and are particularly well oriented for surface deposition. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Divergent Synthesis of Molecular Winch Prototypes
Abid, Seifallah,Gisbert, Yohan,Kammerer, Claire,Rapenne, Gwéna?l
supporting information, p. 16242 - 16249 (2021/10/16)
We report the synthesis of conceptually new prototypes of molecular winches with the ultimate aim to investigate the work performed by a single ruthenium-based molecular motor anchored on a surface by probing its ability to pull a load upon electrically-driven directional rotation. According to a technomimetic design, the motor was embedded in a winch structure, with a long flexible polyethylene glycol chain terminated by an azide hook to connect a variety of molecular loads. The structure of the motor was first derivatized by means of two sequential cross-coupling reactions involving a penta(4-halogenophenyl)cyclopentadienyl hydrotris(indazolyl)borate ruthenium(II) precursor and the resulting benzylamine derivative was next exploited as key intermediate in the divergent synthesis of a family of nanowinch prototypes. A one-pot method involving sequential peptide coupling and Cu-catalyzed azide-alkyne cycloaddition was developed to yield four loaded nanowinches, with load fragments encompassing triptycene, fullerene and porphyrin moieties.
Method for preparing N-(5-carboxyl-2-methylphenyl)-4-(3-pyridine)-2-pyrilamine
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Paragraph 0031; 0032, (2021/05/05)
The invention discloses a method for preparing N-(5-carboxyl-2-methylphenyl)-4-(3-pyridine)-2-pyrilamine. The method specifically comprises the following steps: step 1, carrying out ethyl esterification reaction on 3-nitro-4-methyl benzoic acid serving as an initial raw material to generate a compound 2; step 2, reducing nitro of the compound 2 through hydrogenation reduction reaction in the presence of palladium on carbon to generate a compound 3; step 3, reacting the compound 3 with a nitrile amine aqueous solution, and then carrying out base exchange to obtain a compound 4; step 4, carrying out cyclization between the compound 4 and a compound 6 to obtain a compound 7; and step 5, hydrolyzing the compound 7 under the action of an alkaline to generate a compound 8, namely N-(5-carboxyl-2-methylphenyl)-4-(3-pyridine)-2-pyrilamine. The method overcomes the defects that in the prior art such as long reaction time, low yield, high cost, difficulty for industrial production, and the like. A preparation method, which is high in yield, is environmentally-friendly, and is suitable for industrial production, is provided.
Investigations into the potential role of metabolites on the anti-leukemic activity of imatinib, nilotinib and midostaurin
Manley, Paul W.
, p. 561 - 570 (2019/09/03)
The efficacy and side-effects of drugs do not just reflect the biochemical and pharmacodynamic properties of the parent compound, but often comprise of cooperative effects between the properties of the parent and active metabolites. Metabolites of imatinib, nilotinib and midostaurin have been synthesised and evaluated in assays to compare their properties as protein kinase inhibitors with the parent drugs. The N-desmethylmetabolite of imatinib is substantially less active than imatinib as a BCR-ABL1 kinase inhibitor, thus providing an explanation as to why patients producing high levels of this metabolite show a relatively low response rate in chronic myeloid leukaemia (CML) treatment. The hydroxymethylphenyl and N-oxide metabolites of imatinib and nilotinib are only weakly active as BCR-ABL1 inhibitors and are unlikely to play a role in the efficacy of either drug in CML. The 3-(R)-HO-metabolite of midostaurin shows appreciable accumulation following chronic drug administration and, in addition to mutant forms of FLT3, potently inhibits the PDPK1 and VEGFR2 kinases (IC50 values 100 nM), suggesting that it might contribute to drug efficacy in acute myeloid leukaemia patients. The case studies discussed here provide further examples of how the synthesis and characterisation of metabolites can make important contributions to understanding the clinical efficacy of drugs.
Design, synthesis and biological evaluation of pyridin-3-yl pyrimidines as potent Bcr-Abl inhibitors
Pan, Xiaoyan,Dong, Jinyun,Gao, Hongping,Wang, Fang,Zhang, Yanmin,Wang, Sicen,Zhang, Jie
, p. 592 - 599 (2014/05/06)
A series of pyridin-3-yl pyrimidines was synthesized and evaluated for their Bcr-Abl inhibitory and anticancer activity. The preliminary results indicated that some compounds were promising anticancer agents. Compounds A2, A8, and A9 exhibited potent Bcr-Abl inhibitory activity, suggesting that aniline containing halogen substituents might be important for biological activity. Molecular docking was carried out to investigate the binding mode of them with Bcr-Abl. Details of synthesis and SAR studies of these compounds are described. A series of phenylaminopyrimidines was designed and synthesized as potent Bcr-Abl inhibitors. The screening of these rationally designed compounds for antitumor activity had identified three candidate leads which could be further optimized to improve the anticancer activities.
Synthesis of symmetric diester-functionalised Troeger's base analogues
Bhuiyan, M. Delower H.,Zhu, Kai-Xian,Jensen, Paul,Try, Andrew C.
supporting information; experimental part, p. 4662 - 4670 (2010/10/19)
The yields of ester-functionalised Troeger's base analogues are dramatically improved by incorporating an electron-donating group on the aromatic ring and/or enhancing solubil- ity of the aniline unit. In addition to 2,8-diester compounds, 1,7-, 3,9- and 4,10-diester-functionalised Troeger's base analogues have been prepared for the first time.
Synthesis and properties of an optically active helical bis-cobaltocenium ion
Gilbert, Adam M.,Katz, Thomas J.,Geiger, William E.,Robben, Matthew P.,Rheingold, Arnold L.
, p. 3199 - 3211 (2007/10/02)
The optically active helical bis-cobaltocenium salt 6 is synthesized, as are two related monocobaltocenium salts, 29 and 30. The structure of 6 is analyzed by X-ray diffraction, which shows that the metals are separated by 8.49 ?. Reducing 6 either electrochemically or with K(Hg) produces species that absorb near 920 nm, but the absorption is not an intervalence transition. It originates instead from isolated Co(II) centers. This is demonstrated by the reduction product of 29, which has only one cobalt, also absorbing at a similar wavelength (λmax, = 957 nm). The optical and ESR spectra imply that the unpaired electron in monoreduced 6 is largely localized on cobalt and that direduced 6 is essentially a Co(II)Co(II) diradical. The difference between two Co(III)/Co(II) reduction potentials of 6, 130 mV, is shown to be appropriate for a conjugated dimetallocene with metals so distant. Crystal data for 6: M = 1275.02; orthorhombic, space group P212121; Z = 4; a = 11.560(4), b = 12.244(3), and c = 41.349(17) ?; V = 5852.5 ?3; R = 0.1137 for 4653 reflections having Fo ≥ nσ(Fo) (n = 7.5).
