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.
The Synthesis of Adamantane Ring Containing Benzimidazole, Benzoxazole, and Imidazo[4,5-e]benzoxazole Derivatives from 3-Aminophenol
Soselia, Marina,Geibel, Irina,Zurabishvili, Davit,Samsoniya, Shota
, p. 447 - 455 (2018)
Adamantane derivatives containing heterocycles such as benzimidazoles, benzoxazoles, and fused imidazo[4,5-e]benzoxazoles were synthesized from 3-aminophenol. The route started with amidation of adamantane-1-carboxylic acid chloride with 3-aminophenol fur
Intermolecular interactions in crystalline 1-(adamantane-1-carbonyl)-3-substituted thioureas with Hirshfeld surface analysis
Saeed, Aamer,Bolte, Michael,Erben, Mauricio F.,Pérez, Hiram
, p. 7551 - 7563 (2015)
The conformationally congested species 1-(adamantane-1-carbonyl)-3-(2,4,6-trimethylphenyl)thiourea has been prepared and fully characterized by elemental analyses, FTIR, 1H NMR, 13C NMR and mass spectrometry. Its crystal structure was determined by single-crystal X-ray diffraction. The dihedral angle between the plane of the 2,4,6-trimethylphenyl group and the plane of the thiourea fragment was optimized by theoretical calculations applying the B3LYP/6-311++G(d,p) level for the purpose of investigating the conformational effects on the stabilization of the crystal packing. A detailed analysis of the intermolecular interactions in a series of six closely related phenylthiourea species bearing the 1-(adamantane-1-carbonyl) group has been performed based on the Hirshfeld surfaces and their associated two-dimensional fingerprint plots. The relative contributions of the main intermolecular contacts as well as the enrichment ratios derived from the Hirshfeld surface analysis establish the 1-acyl thiourea synthon to be a widespread contributor.
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.
Noncovalent binding of sensitizers for lanthanide(III) luminescence in an EDTA-bis(β-cyclodextrin) ligand
Michels, Jasper J.,Huskens, Jurriaan.,Reinhoudt, David N.
, p. 2056 - 2064 (2002)
EDTA-linked β-cyclodextrin dimer 3 was synthesized from EDTA bis(anhydride) 1 and mono-(propylamino)-appended β-cyclodextrin 2. p-tert-Butylbenzoate 5, bound by the β-cyclodextrin cavities of 3 with an association constant of 104 M-1 in water, acts as a sensitizer for the EuIII and TbIII complexes of 3. Luminescence spectroscopy, microcalorimetry, and GdIII-induced NMR relaxation rate measurements prove that 3 forms a 1:2 complex with 5 and that one of the β-cyclodextrin-bound sensitizers coordinates to the EDTA-encapsulated LnIII ion. The EuIII complex of 3 forms strong 1:1 complexes (K ≈ 107 M-1) with bis(propylamido adamantyl)-functionalized biphenyl sensitizers 7 and 8 in water. Both β-cyclodextrins of 3 are involved in the binding of these guests. The amide functionality adjacent to the biphenyl unit in 7 and 8 coordinates to the EDTA-encapsulated LnIII ion. For these biphenyl-based antennae both binding to β-cyclodextrin and coordination to the LnIII center are crucial for efficient sensitization.
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.
Construction and DNA condensation of cyclodextrin-coated gold nanoparticles with anthryl grafts
Zhao, Di,Chen, Yong,Liu, Yu
, p. 1895 - 1903 (2014)
The condensation of DNA in a controlled manner is one of the key steps in gene delivery and gene therapy. For this purpose, a water-soluble supramolecular nanostructure is constructed by coating 14 β-cyclodextrins onto the surface of a gold nanoparticle, followed by the noncovalent association of different amounts of anthryl-modified adamantanes with coated β-cyclodextrins. The strong binding of β-cyclodextrins with anthryl adamantanes (KS=8.61×104 M-1) efficiently stabilizes the supramolecular nanostructure. Spectrophotometric fluorescence spectra and microscopic studies demonstrated that, with many anthryl grafts that can intercalate in the outer space of the DNA double helix, this supramolecular nanostructure showed good condensation abilities to calf thymus DNA. Significantly, the condensation efficiency of supramolecular nanostructure towards DNA could be conveniently controlled by adjusting the ratio between gold nanoparticles and anthryl adamantane grafts, leading to the formation of DNA condensates of a size that are suitable for the endocytosis of hepatoma cells, which will make it potentially applicable in many fields of medicinal science and biotechnology. Congenial host: A supramolecular DNA condenser containing gold nanoparticles (AuNPs; see picture), β-cyclodextrins (CDs), and anthryl adamantanes exhibits good DNA condensation efficiency and low toxicity; thus making it potentially applicable in medicinal science and biotechnology.
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.
Construction of a novel INHIBIT logic gate through a fine-tuned assembly of anthryl fluorophores via selective anion recognition and host-guest interactions
Zhang, Lei,He, Yilong,Zhang, Na,Liu, Daosheng,Han, Jiao,Gong, Weitao
, p. 805 - 809 (2015)
A novel ligand (AAP) based on an anthryl fluorophore was rationally designed and synthesized. The presence of H2PO4- (Pi) could induce the effective assembly of the ligand which leads to a strong excimer emission, while β-cyclodextrin (β-CD) disassembled the Pi-ligand complex through a host-guest interaction with terminal adamantane groups. This disassembly causes a considerable decrement in emissive intensity as well as a clear blue-shift in emissive wavelength. By manipulating the assembly and disassembly of anthryl fluorophores with Pi and β-CD, a novel INHIBIT logic gate was constructed using Pi and β-CD as the chemical inputs and fluorescence emission as the output.
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.
