2094-72-6Relevant articles and documents
Adamantylated organosilatranes: Design, synthesis, and potential appraisal in surface modification and anti-protozoal activity
Singh, Gurjaspreet,Rani, Sunita,Gawri, Sanchita,Sinha, Shweta,Sehgal, Rakesh
, p. 11626 - 11639 (2017)
The present investigation evaluates the design and facile synthesis of a series of organosilatranes (1-7) tethered with the privileged adamantane motif, labelled as a 'lipophilic bullet', via numerous biocompatible linkages i.e. amide, ester, thioester, urea, thiourea, and thiocarbamate groups. The assembled silatranes have been scrupulously characterized by elemental analysis, FT-IR and NMR (1H and 13C) spectroscopy, and mass spectrometry. The parasitic diseases caused by unicellular protozoa, Giardia lamblia (G. lamblia) and Trichomonas vaginalis (T. vaginalis), represent a major health burden, therefore the synthesized compounds were probed for in vitro giardicidal and trichomonacidal activities. With this aim, firstly the pharmacokinetic profiles of the compounds were scrutinized using absorption, distribution, metabolism, excretion, and toxicity (ADMET) tools and on the whole, all compounds showed good oral bioavailability. The anti-parasitic activity of the newly synthesized compounds was evaluated in comparison to a standard drug (metronidazole) by 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) assay. All the compounds displayed significant activity against G. lamblia and T. vaginalis with IC50 values ranging from 10.9-127.4 μM and 6.2-128.9 μM, respectively. To improve the aqueous solubility of the synthesized compounds, the enticing feature of the adamantane moiety to undergo inclusion binding with the β-cyclodextrin cavity is explored. Furthermore, a simplistic methodology is proposed to covalently anchor adamantylated silatrane onto the surface of magnetic silica nanoparticles. This material promises to be a non-invasive and externally controlled drug delivery system with enormous anti-protozoal potential.
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Razuvajev et al.
, p. 4925,4929 (1969)
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A novel self-healing power cable insulating material based on host-guest interactions
Peng, Lei,Zhang, Manjun,Lin, Musong,Fu, Qiang
, p. 25313 - 25318 (2018)
The insulating materials used in power cables are susceptible to damage and cracks during installation and operation. To solve this problem, we have prepared a self-healing material PVP/p(HEMA-co-BA), which is synthesized by radical polymerization using HEMA, BA, PVP and a host-guest assembly. The host-guest assembly is constructed through interactions between host and guest molecules (CD-Al2O3 NPs act as the host, and HEMA-Ad acts as the guest). The characterization results of the materials show that there are two kinds of supramolecular interactions, namely, the host-guest interaction and the hydrogen bonding. The material possesses good thermal stability (heat-resisting temperature can reach 200 °C) and good electrical performance. The storage modulus of the material can be increased up to 432 MPa using a cross-linking agent at 20 °C. Furthermore, the material exhibits self-healing property, and it can self-heal several times; its self-healing efficiency is relative to the dosage of the cross-linking agent.
Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies
Milo?ev, Milorad Z.,Jakovljevi?, Katarina,Joksovi?, Milan D.,Stanojkovi?, Tatjana,Mati?, Ivana Z.,Perovi?, Milka,Te?i?, Vesna,Kanazir, Selma,Mladenovi?, Milan,Rodi?, Marko V.,Leovac, Vukadin M.,Trifunovi?, Sne?ana,Markovi?, Violeta
, p. 943 - 952 (2017)
A series of 18 novel N-Mannich bases derived from 5-adamantyl-1,2,4-triazole-3-thione was synthesized and characterized using NMR spectroscopy and X-ray diffraction technique. All derivatives were evaluated for their anticancer potential against four human cancer cell lines. Several tested compounds exerted good cytotoxic activities on K562 and HL-60 cell lines, along with pronounced selectivity, showing lower cytotoxicity against normal fibroblasts MRC-5 compared to cancer cells. The effects of compounds 5b, 5e, and 5j on the cell cycle were investigated by flow cytometric analysis. It was found that these compounds cause the accumulation of cells in the subG1 and G1 phases of the cell cycle and induce caspase-dependent apoptosis, while the anti-angiogenic effects of 5b, 5e, and 5j have been confirmed in EA.hy926 cells using a tube formation assay. Further, the interaction of Bax protein with compound 5b was investigated by means of molecular modeling, applying the combined molecular docking/molecular dynamics approach.
Synthesis, X-ray, Hirshfeld surface analysis, exploration of DNA binding, urease enzyme inhibition and anticancer activities of novel adamantane-naphthyl thiourea conjugate
Arshad, Nasima,Saeed, Aamer,Perveen, Fouzia,Ujan, Rabail,Farooqi, Shahid I.,Ali Channar, Pervaiz,Shabir, Ghulam,El-Seedi, Hesham R.,Javed, Aneela,Yamin, Maham,Bolte, Michael,H?kelek, Tuncer
, (2021)
1-(adamantane-1-carbonyl-3-(1-naphthyl)) thiourea (C22H24N2OS (4), was synthesized by the reaction of freshly prepared adamantane-1-carbonyl chloride from corresponding acid (3) with ammonium thiocyanate in 1:1 M ratio in dry acetone to afford the adamantane-1-carbonyl isothiocyanate (2) in situ followed by treatment with 1-naphthyl amine (3). The structure was established by elemental analyses, FTIR, 1H, 13C NMR and mass spectroscopy. The molecular and crystal structure were determined by single crystal X-ray analysis. It belongs to triclinic system P ? 1 space group with a = 6.7832(5) ?, b = 11.1810(8) ?, c = 13.6660(10) ?, α = 105.941(6)°, β = 103.730(6)°, γ = 104.562(6)°, Z = 2, V = 910.82(11) ?3. The naphthyl group is almost planar. In the crystal structure, intermolecular C[sbnd]H···O hydrogen bonds link the molecules into centrosymmetric dimers, enclosing R22(14) ring motifs, while the intramolecular N[sbnd]H···O hydrogen bonds enclose S(6) ring motifs, in which they may be effective in the stabilization of the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H … H (59.3%), H … C/C … H (19.8%) and H … S/S … H (10.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. DFT, molecular docking and urease inhibition studies revealed stability and electron withdrawing nature of 4 as compared to DNA base pairs and residues of urease. The DNA binding results from docking, UV– visible spectroscopy, and viscosity studies indicated significant binding of 4 with the DNA via intercalation and groove binding. Further investigation of the compound was done on hepatocellular carcinoma; Huh-7 cell line as well as normal human embryonic kidney; Hek-293 cell line. The compound showed significant cytotoxic activity against Huh-7 cells in comparison to normal Hek-293 cells indicating selective cytotoxicity towards cancer cells.
Conductive Elastomers with Autonomic Self-Healing Properties
Guo, Kun,Zhang, Da-Li,Zhang, Xiao-Mei,Zhang, Jian,Ding, Li-Sheng,Li, Bang-Jing,Zhang, Sheng
, p. 12127 - 12133 (2015)
Healable, electrically conductive materials are highly desirable and valuable for the development of various modern electronics. But the preparation of a material combining good mechanical elasticity, functional properties, and intrinsic self-healing ability remains a great challenge. Here, we design composites by connecting a polymer network and single-walled carbon nanotubes (SWCNTs) through host-guest interactions. The resulting materials show bulk electrical conductivity, proximity sensitivity, humidity sensitivity and are able to self-heal without external stimulus under ambient conditions rapidly. Furthermore, they also possess elasticity comparable to commercial rubbers.
Directed C?H Bond Oxidation of Bridged Cycloalkanes Catalyzed by Palladium(II) Acetate
Larrosa, Marta,Zonker, Benjamin,Volkmann, Jannis,Wech, Felix,Logemann, Christian,Hausmann, Heike,Hrdina, Radim
, p. 6269 - 6276 (2018)
We have developed a synthesis of 1,2-substituted adamantane carboxylic acids and further bridged cycloalkanes (cage compounds) by palladium acetate-catalyzed C?H bond oxidation. Acetoxylation of cycloalkane framework was performed using picolylamide as a directing group. Modification of the substrate, ligand design and variation of reaction conditions enabled us to study the mechanism of acetoxylation of aliphatic compounds. Post-functionalization reactions and cleavage of the directing group were developed. For the first time the synthesis and characterization of a β-C3-tri-substituted adamantane derivatives was achieved.
Activation of Sirtuin 2 Inhibitors Employing Photoswitchable Geometry and Aqueous Solubility
Grathwol, Christoph W.,W?ssner, Nathalie,Behnisch-Cornwell, Steven,Schulig, Lukas,Zhang, Lin,Einsle, Oliver,Jung, Manfred,Link, Andreas
, p. 1480 - 1489 (2020)
Because isoenzymes of the experimentally and therapeutically extremely relevant sirtuin family show high similarity, addressing the unique selectivity pocket of sirtuin 2 is a promising strategy towards selective inhibitors. An unrelated approach towards selective inhibition of isoenzymes with varied tissue distribution is targeted drug delivery or spatiotemporal activation by photochemical activation. Azologization of two nicotinamide-mimicking lead structures was undertaken to combine both approaches and yielded a set of 33 azobenzenes and azopyridines that have been evaluated for their photochemical behaviour and bioactivity. For some compounds, inhibitory activity reached the sub-micromolar range in their thermodynamically favoured E form and could be decreased by photoisomerization to the metastable Z form. Besides, derivatization with long-chain fatty acids yielded potent sirtuin 2 inhibitors, featuring another intriguing aspect of azo-based photoswitches. In these compounds, switching to the Z isomer increased aqueous solubility and thereby enhanced biological activity by up to a factor of 21. The biological activity of two compounds was confirmed by hyperacetylation of sirtuin specific histone proteins in a cell-based activity assay.
Fluorous 1,2,3-Triazol-4-ylmethyl Amines and Amine Derivatives for Novel Surfactant Applications
Francis, Dominic V.,Harper, Jason B.,Read, Roger W.
, p. 57 - 68 (2015)
A series of fluorous surfactants with additional functionality were generated through the attachment of substituents at the amino nitrogen atom of the surfactant moiety. Examples of molecules containing one and two triazole ring systems were synthesized through N-alkylation and N-acylation strategies.
Structural Basis of Nanomolar Inhibition of Tumor-Associated Carbonic Anhydrase IX: X-Ray Crystallographic and Inhibition Study of Lipophilic Inhibitors with Acetazolamide Backbone
Andring, Jacob T.,Fouch, Mallorie,Akocak, Suleyman,Angeli, Andrea,Supuran, Claudiu T.,Ilies, Marc A.,McKenna, Robert
, p. 13064 - 13075 (2020/11/20)
This study provides a structure-Activity relationship study of a series of lipophilic carbonic anhydrase (CA) inhibitors with an acetazolamide backbone. The inhibitors were tested against the tumor-expressed CA isozyme IX (CA IX), and the cytosolic CA I, CA II, and membrane-bound CA IV. The study identified several low nanomolar potent inhibitors against CA IX, with lipophilicities spanning two log units. Very potent pan-inhibitors with nanomolar potency against CA IX and sub-nanomolar potency against CA II and CA IV, and with potency against CA I one order of magnitude better than the parent acetazolamide 1 were also identified in this study, together with compounds that displayed selectivity against membrane-bound CA IV. A comprehensive X-ray crystallographic study (12 crystal structures), involving both CA II and a soluble CA IX mimetic (CA IX-mimic), revealed the structural basis of this particular inhibition profile and laid the foundation for further developments toward more potent and selective inhibitors for the tumor-expressed CA IX.