14002-51-8Relevant academic research and scientific papers
Thioester-appended organosilatranes: Synthetic investigations and application in the modification of magnetic silica surfaces
Singh, Gurjaspreet,Rani, Sunita,Arora, Aanchal,Aulakh, Darpandeep,Wriedt, Mario
, p. 6200 - 6213 (2016)
The present investigation discloses a series of new organosilicon derivatives (3a-k) tailored with substituted benzoic acid modules (1a-k) via thioesterification with 3-mercaptopropylsilatrane (MPS). Product formation was authenticated using elemental analyses and different spectroscopic methods comprising FT-IR, NMR [1H, 13C] and LC-MS (Q-TOF). Thereafter, complete structural elucidation of compounds 3c and 3f was achieved by the single crystal X-ray technique. Photo-electronic inspection of all compounds by UV-Vis spectroscopy revealed their sensitivity towards substitution patterns. In addition, this is the first time that the potential of a silatranyl moiety has been tested for the modification of a silica surface pre-decorated with a magnetite core. The synthesis was achieved through a facile methodology involving chemical bonding at each stage, which proceeded without any external surfactant or template. The course of the reaction was followed by FT-IR, UV-Vis, XRD, TEM, FESEM, EDX and TGA techniques. Furthermore, the hybrid nanomaterial possessed significant sensorial ability toward copper ions, which makes the present protocol favourable for the construction of a new class of chelating ligands with an in-built multifunctional nanodevice.
Amide-tethered organosilatranes: Syntheses, structural characterization and photophysical properties
Singh, Gurjaspreet,Rani, Sunita,Saroa, Amandeep,Promila,Arora, Aanchal,Choquesillo-Lazarte, Duane
, p. 78 - 91 (2015)
A series of trimethoxysilanes and silatranes coupled with distinct aromatic moieties (biphenyl, thiophene, pyrazine and pyridine) through amide linkage are reported. The synthetic approach involved the amidation of 3-aminopropyltrimethoxysilane (APTMS) with various carboxylic acids via acid chlorides (1a-1g) to generate amidopropylsilanes (2a-2g). Transesterification of the resultant silanes with triethanolamine and tris(isopropanolamine) yielded unsubstituted (3a-3g) and 3,7,10-trimethylsubstitued organosilatranes (4a-4g), respectively. The compounds were successfully characterized by various spectroscopic techniques [IR, NMR (1H, 13C) and Mass] and elemental analysis. The complete structure elucidation for compounds 3a, 3c·H2O and 3f was carried out using single crystal X-ray diffraction analysis. The photophysical response was studied by UV-Vis absorption and fluorescence spectroscopy. These organosilatranes possess metal ion binding sites and can be put forth for advanced analytical applications.
Regulation of a cerium(iv)-driven O2 evolution reaction using composites of liposome and lipophilic ruthenium complexes
Koshiyama, Tomomi,Kanda, Nao,Iwata, Koki,Honjo, Masayuki,Asada, Sana,Hatae, Tatsuru,Tsuji, Yasuhiro,Yoshida, Masaki,Okamura, Masaya,Kuga, Reiko,Masaoka, Shigeyuki,Ohba, Masaaki
, p. 15126 - 15129 (2015)
A composite containing a liposome and a lipophilic ruthenium complex was synthesized to regulate an O2 evolution reaction using cerium(iv) ammonium nitrate as an oxidizing reagent. We found that the surrounding environment of the reaction centre is an important factor for controlling the O2 evolution catalytic reaction. We successfully regulated the reaction activity using the linker length of the lipophilic ligand and using the head groups of the phospholipid component.
Design and synthesis of N-benzoyl amino acid derivatives as DNA methylation inhibitors
Garella, Davide,Atlante, Sandra,Borretto, Emily,Cocco, Mattia,Giorgis, Marta,Costale, Annalisa,Stevanato, Livio,Miglio, Gianluca,Cencioni, Chiara,Fernández-de Gortari, Eli,Medina-Franco, José L.,Spallotta, Francesco,Gaetano, Carlo,Bertinaria, Massimo
, p. 664 - 676 (2016)
The inhibition of human DNA Methyl Transferases (DNMT) is a novel promising approach to address the epigenetic dysregulation of gene expression in different diseases. Inspired by the validated virtual screening hit NSC137546, a series of N-benzoyl amino acid analogues was synthesized and obtained compounds were assessed for their ability to inhibit DNMT-dependent DNA methylation in vitro. The biological screening allowed the definition of a set of preliminary structure–activity relationships and the identification of compounds promising for further development. Among the synthesized compounds, L-glutamic acid derivatives 22, 23, and 24 showed the highest ability to prevent DNA methylation in a total cell lysate. Compound 22 inhibited DNMT1 and DNMT3A activity in a concentration-dependent manner in the micromolar range. In addition, compound 22 proved to be stable in human serum and it was thus selected as a starting point for further biological studies.
Purposeful regioselectivity control of the Birch reductive alkylation of biphenyl-4-carbonitrile
Fedyushin, Pavel A.,Peshkov, Roman Yu.,Panteleeva, Elena V.,Tretyakov, Evgeny V.,Beregovaya, Irina V.,Gatilov, Yuri V.,Shteingarts, Vitalij D.
, p. 842 - 851 (2018)
Birch's reductive alkylation of biphenyl-4-carbonitrile (1) provides alkylated 1,4-dihydroderivatives of various structural types: 4-alkyl-4-phenylcyclohexa-2,5-dienone, 1,4-dialkyl-4-phenylcyclohexa-2,5-dienecarbonitrile (with the same or different alkyl fragments), and 4-(1-alkylcyclohexa-2,5-dienyl)benzonitrile. Each of these products become dominant depending on the nature of long-living anionic form generated from 1, namely, the stable product of two-electrons reduction – dianion (12?); 1-alkyl-4-cyano-1-phenylcyclohexa-2,5-dien-4-yl anion (1-Alk1–), originated due to the alkylation of dianion 12? at the position 1 of biphenyl moiety; or 1-(4-cyanophenyl)cyclohexa-2,5-dien-1-yl anion (1-H4’–), being the product of dianion 12? protonation at position 4′ by protonating reagent (MeOH or NH4Cl). The orientation of alkyl fragment incorporation into biphenyl-4-carbonitrile scaffold is in agreement with calculated electronic structure of the anionic species under investigation. The dominating type of their reactivity towards alkyl halides proved to be nucleophilic (SN2 mechanism).
An expedient ‘click’ approach for the synthetic evaluation of ester-triazole-tethered organosilica conjugates
Singh, Gurjaspreet,Rani, Sunita
, (2018)
The present work articulates the synthesis of a new series of organo-functionalized triethoxysilanes derived from versatile carboxylic acids and 3-azidopropyltriethoxysilane in excellent yields. A proficient and convenient route implicating the Cu(I)-catalysed 1,3-cycloaddition of organic azide with terminal alkynes, labelled as click silylation, has been developed for the generation of ester-triazole-linked alkoxysilanyl scaffolds (4a–f). All the synthesized compounds have been thoroughly characterized using elemental analysis and Fourier transform infrared, 1H NMR and 13C NMR spectroscopic techniques. Importantly, the fabricated alkoxysilanes are potentially amenable for an in situ sol–gel condensation reaction with silica nanospheres leading to the incorporation of organic functionality via covalent grafting onto the nanostructured particle system. As a proof of concept, a one-pot preparation of organic–inorganic hybrid nanoparticles is presented using bis-silane 4?f. The efficiency and selectivity of the prepared nanocomposite towards metal ions is highlighted using adsorption experiments, and the immobilized nanoparticles present a high sensing efficiency towards Cu2+ and Pb2+ ions while demonstrating better response than that of the bulk material.
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters
Nikitas, Nikolaos F.,Apostolopoulou, Mary K.,Skolia, Elpida,Tsoukaki, Anna,Kokotos, Christoforos G.
supporting information, p. 7915 - 7922 (2021/05/03)
A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.
Process production method of (2'R)-2'-deoxy-2'-fluoro-2'-methyluridine
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Paragraph 0034-0035, (2020/09/12)
The invention discloses a process production method of (2'R)-2'-deoxy-2'-fluoro-2'-methyluridine. The method comprises the following steps of: by taking (2R)-2-deoxy-2-fluoro-2-methyl-D-erythropentanoic acid GAMMA-lactone as a raw material, carrying out a
KDM4B INHIBITORS FOR THE TREATMENT OF INFLAMMATORY DISEASES AND DISORDERS
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, (2020/12/29)
The invention relates to KDM4B inhibitors, compositions comprising an effective amount of KDM4B inhibitors and methods for treating inflammatory diseases and disorders.
