29713-15-3Relevant academic research and scientific papers
Synthesis, physiochemical property and antibacterial activity of gemini quaternary ammonium salts with a rigid spacer
Fu,Guo,Zhong,Yang,Lai
, p. 16507 - 16515 (2016)
A novel series of adamantane-based gemini quaternary ammonium salts (GQASs) named as m-Ad-m (bromides, alkyl chain length, m = 12, 14, 16) are synthesized from 1,3-adamantanedicarboxylic acid. Their chemical structures are confirmed by 1H NMR, FT-IR and ESI-MS. The surface activities in aqueous solutions of m-Ad-m are evaluated by surface tension. Unlike conventional GQASs with a flexible spacer, m-Ad-m possessing a rigid adamantane spacer show lower surface tension (γCMC) values as compared to conventional GQASs bearing the same alkyl chains. The thermodynamic properties of m-Ad-m are examined by electrical conductivity measurements at different temperatures, including molecular interaction parameters (β), standard Gibbs free energy (ΔG0m), enthalpy (ΔH0m) and entropy (ΔS0m), which show that the micellization of m-Ad-m is entropy-driven. TEM study exhibits that the aggregate morphologies of m-Ad-m change from micelles and spheroidal vesicles of varying size to network aggregates and then to globular vesicles with the increase in m-Ad-m concentration. Furthermore, the antimicrobial efficacy of m-Ad-m against both Gram-positive bacteria (S. aureus and B. subtilis) and Gram-negative bacteria (E. coli, P. aeruginosa and V. parahaemolyticus) is systematically studied by minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) methods, which indicates the favorable antibacterial activity of 12-Ad-12 against the studied bacteria.
Synthesis, surface property and antimicrobial activity of cationic gemini surfactants containing adamantane and amide groups
Zhong, Xing,Guo, Jianwei,Fu, Shuqin,Zhu, Dongyu,Peng, Jinping
, p. 943 - 950 (2014)
A series of novel cationic gemini surfactants, namely 1,3- adamantanedicarboxylic acid bis(alkyldimethyl-3-ammoniopropyl amide) dibromide designated as [Ad-2(amC n )] (n = 12, 14, 16), containing adamantane, two amide groups, and two hydrocarbon chains, were synthesized from 1,3-adamantanedicarboxylic acid. The surface-active properties of the surfactants were investigated through surface tension and electrical conductivity measurement. A series of thermodynamic parameters such as standard free energy (ΔG°m), enthalpy (ΔH°m), and entropy (ΔS°m) of micellization were evaluated from electrical conductivity measurements in the temperature range from 288 to 308 K. The micellization for [Ad-2(amC n )] is entropy-driven at low temperature and enthalpy-driven at high temperature. Further, the antimicrobial activity of the synthesized gemini surfactants against both Gram-positive and Gram-negative bacteria was also investigated, and this study showed that the compound [Ad-2(amC12)] has excellent antibacterial activity against all studied bacteria.
A photosensitive semi-alicyclic poly(benzoxazole) with high transparency and low dielectric constant
Fukukawa, Ken-Ichi,Shibasaki, Yuji,Ueda, Mitsuru
, p. 8256 - 8261 (2004)
A photosensitive semi-alicyclic poly(benzoxazole) based on poly(o-hydroxy amide) containing adamantyl units (PAHA) and 1,3,5-tris[(2-vinyloxy)ethoxy] benzene (TVEB) as an acidolytic de-cross-linker and a photoacid generator, diphenyliodonium 9,10-dimethoxyanthracene-2-sufonate (DIAS), has been developed. PAHA with a weight-average molecular weight of 24 100 was prepared from 1,3-adamantanedicarbonyl chloride (ADG) and 4,4′- (hexafluoroisopropylidene)bis(o-aminophenol) (6FAP) in the presence of lithium chloride in N-methylpyrrolidinone (NMP) at 0°C for 12 h. By thermal treatment, PAHA was easily converted to semi-alicyclic poly(benzoxazole) (PABO) that was insoluble in organic solvents and showed high thermal stability (I d5 = 520°C under Ns). The UV-vis spectra of PAHA and PABO indicated excellent transparency at wavelengths above 320 and 400 nm, respectively. The average refractive index of PABO was 1.523, and the dielectric constant estimated from the refractive index was 2.55 at 1 MHz. This value is significantly lower than those of conventional wholly aromatic PBOs. The photosensitive PABO precursor, PAHA containing 15 wt % TVEB and 5 wt % DIAS, showed a sensitivity of 40 mJ/cm2 and a contrast of 4.0 when it was exposed to a 365 nm light (i-line) and developed with a 2.38 wt % aqueous tetramethylammonium hydroxide solution (TMAHaq) at 25°C. A fine positive image of 10 μm line-and-space pattern was also printed in a film which was exposed to 70 mJ/cm2 of i-line by contact-printing mode. The positive image in PAHA was converted to the positive image in the PABO film by the thermal treatment without pattern deformation.
Preparation of diisocyanates of adamantane and diamantane
Davis, Matthew C.,Dahl, Jeremy E. P.,Carlson, Robert M. K.
, p. 1153 - 1158 (2008)
The 1,6- and 4,9-diisocyanates of diamantane have been prepared for the first time by treatment of the corresponding diamines with triphosgene. Also, 1,3-diisocyanatoadamantane was prepared through double Curtius rearrangement of 1,3-adamantanedicarboxylic acid. Copyright Taylor & Francis Group, LLC.
Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors
Leite, Irena,Andrianov, Victor,Zelencova-Gopejenko, Diana,Loza, Einars,Kazhoka-Lapsa, Iveta,Domracheva, Ilona,Stoyak, Marta,Chlopicki, Stefan,Kalvins, Ivars
, p. 1086 - 1106 (2022/01/12)
[Figure not available: see fulltext.] Acyl derivatives of aziridine-2-carboxylic acid have been synthesized and tested as PDIA1 inhibitors. Calculations of charge value and distribution in aziridine ring system and some alkylating agents were performed. For the first time was found that acyl derivatives of aziridine-2-carboxylic acid are weak to moderately active PDIA1 inhibitors.
Four-Directional synthesis of adamantane derivatives
Qu, Tao,White, Andrew J. P.,Barrett, Anthony G. M.
, p. 18 - 50 (2020/08/28)
1-Adamantanemethanol, 1,3-adamantanedimethanol and 1,3,5,7-adamantanetetramethanol were converted into adamantanes functionalized with one or four (2R,1S)-2-formyl-1-cyclopropyl residues using Charette enantioselective cyclopropanation reactions and with one, two or four 4-ethoxy- (or 4-t-butoxy)-3-diazo-2,4- dioxobutyl residues from aldehyde and diazo-acetate ester condensation reactions by 1-directional, 2- directional or 4-directional syntheses. The synthesis of adamantane fused to cyclopentadiene is also reported. 'Equation Presented'.
Synthesis method and application of compound methyl 5-fluorouracil adamantane carboxylate
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Paragraph 0023; 0028-0029, (2019/11/29)
The invention discloses a synthesis method of a new compound methyl 5-fluorouracil adamantane carboxylate, and an application of the compound as an antitumor drug. The synthesis method of the compoundis characterized in that 1,3-adamantanedicarbonyl chloride and hydroxymethylfluorouracil undergo an esterification reaction to obtain the methyl 5-fluorouracil adamantane carboxylate. The compound has a certain anticancer activity to intestinal cancer cell lines.
CYCLIC PEPTIDES MULTIMERS TARGETING α4β7 INTEGRIN
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Page/Page column 29; 30; 106, (2018/05/27)
There is described herein, multimers comprising a plurality of compounds covalently linked together, the compounds independently being of formula (I).
Generation of liquid crystallinity from a Td-symmetry central unit
Sayed, Sayed Mir,Lin, Bao-Ping,Yang, Hong
, p. 6148 - 6156 (2016/07/26)
A series of new columnar liquid crystals containing an adamantane central unit with its four bridgehead positions partially or fully decorated with different numbers (1-4) of 3,4,5-tris(dodecyloxy)phenyl carbamoyl groups were designed and investigated carefully to explore the structure-property correlations. The molecular structures and mesomorphic properties of the DLCs were characterized by 1H-NMR, 13C-NMR, IR, UV-vis, POM, DSC and XRD. It was found that the mesophase symmetry and thermal stability were extremely dependent on the structures of the adamantane derivatives. No mesophase was observed for the 1-adamantanecarboxylic acid derivative ADLC1, while two different mesophases were observed for ADLC2, a 1,3-disubstituted derivative functionalized with two 3,4,5-tris(dodecyloxy)phenyl carbamoyl groups at two symmetric bridgehead positions. At lower temperature ADLC2 exhibited a rectangular columnar phase, which switched to a square columnar phase possessing a wide temperature range. Similarly, a hexagonal columnar mesophase was observed for the bridgehead trisubstituted adamantane molecule ADLC3. Interestingly, the fully bridgehead-functionalized 1,3,5,7-tetrasubstituted adamantane compound ADLC4 completely lost liquid crystallinity.
Substrate scope in the copper-mediated construction of bis-oxindoles via a double C-H/Ar-H coupling process
Drouhin, Pauline,Hurst, Timothy E.,Whitwood, Adrian C.,Taylor, Richard J.K.
supporting information, p. 7124 - 7136 (2015/03/30)
Abstract The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)2·H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method.
