- Synthesis, physiochemical property and antibacterial activity of gemini quaternary ammonium salts with a rigid spacer
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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.
- Fu,Guo,Zhong,Yang,Lai
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- Synthesis, surface property and antimicrobial activity of cationic gemini surfactants containing adamantane and amide groups
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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.
- Zhong, Xing,Guo, Jianwei,Fu, Shuqin,Zhu, Dongyu,Peng, Jinping
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- A photosensitive semi-alicyclic poly(benzoxazole) with high transparency and low dielectric constant
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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.
- Fukukawa, Ken-Ichi,Shibasaki, Yuji,Ueda, Mitsuru
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- Preparation of diisocyanates of adamantane and diamantane
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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.
- Davis, Matthew C.,Dahl, Jeremy E. P.,Carlson, Robert M. K.
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- Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors
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[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.
- Leite, Irena,Andrianov, Victor,Zelencova-Gopejenko, Diana,Loza, Einars,Kazhoka-Lapsa, Iveta,Domracheva, Ilona,Stoyak, Marta,Chlopicki, Stefan,Kalvins, Ivars
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p. 1086 - 1106
(2022/01/12)
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- Four-Directional synthesis of adamantane derivatives
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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'.
- Qu, Tao,White, Andrew J. P.,Barrett, Anthony G. M.
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- Synthesis method and application of compound methyl 5-fluorouracil adamantane carboxylate
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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.
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Paragraph 0023; 0028-0029
(2019/11/29)
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- CYCLIC PEPTIDES MULTIMERS TARGETING α4β7 INTEGRIN
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There is described herein, multimers comprising a plurality of compounds covalently linked together, the compounds independently being of formula (I).
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Page/Page column 29; 30; 106
(2018/05/27)
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- Generation of liquid crystallinity from a Td-symmetry central unit
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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.
- Sayed, Sayed Mir,Lin, Bao-Ping,Yang, Hong
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p. 6148 - 6156
(2016/07/26)
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- Substrate scope in the copper-mediated construction of bis-oxindoles via a double C-H/Ar-H coupling process
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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.
- Drouhin, Pauline,Hurst, Timothy E.,Whitwood, Adrian C.,Taylor, Richard J.K.
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supporting information
p. 7124 - 7136
(2015/03/30)
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- Oxidation coloring compound and application thereof
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PROBLEM TO BE SOLVED: To provide a new compound having characters such as high sensitivity suitable for oxidation coloring reagent such as hydrogen peroxide quantitation and also having excellent light stability. SOLUTION: Provided is a compound represented by the formula (I) or a salt thereof. [R1 and R2 are each independently a 4-disubstituted aminoaryl group, aryl groups of R1 and R2 may be bound to each other via S or O, and at least one position of aryl groups of R1 and R2 may be substituted with a sulfonic acid group, A is an adamantanylene group, and X is a functional or atomic group represented by the formula (X-1) or the like.] COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0034
(2016/11/17)
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- Copper-mediated construction of spirocyclic bis-oxindoles via a double C-H, Ar-H coupling process
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A double C-H, Ar-H coupling process for the conversion of bis-anilides into spirocyclic bis-oxindoles, enabling the concomitant formation of two all-carbon quaternary centers at oxindole 3-positions in a diastereoselective manner, is described. The optimum cyclization conditions utilize stoichiometric Cu(OAc)2·H2O/KOtBu in DMF at 110 °C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28-77%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.
- Drouhin, Pauline,Hurst, Timothy E.,Whitwood, Adrian C.,Taylor, Richard J.K.
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supporting information
p. 4900 - 4903
(2015/04/27)
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- Efficient synthesis of 1,3-adamantanedicarboxylic acid and 1,3-diaminoadamantane
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1,3-Adamantane dicarboxylic acid was efficiently synthesized from 1-adamantane carboxylic acid by one-pot method. 1,3- Diaminoadamantane was synthesized from 1,3-adamantane dicarboxylic acid via amidation reaction and Hofmann degradation. The structure was confirmed by NMR spectra, etc.
- Zhu, Hua,Zhong, Xin
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p. 4119 - 4120
(2013/06/04)
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- (1-Adamantyl)methyl esters: Whole-molecule disorder in the crystal structure of (1-adamantyl)methyl-1-adamantanecarboxylate
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Two (1-adamantyl)methyl esters, (1-adamantyl)methyl-1-adamantanecarboxylate (1) and bis[(1adamantyl)methyl]-1,3-adamantanedicarboxylate (2) were prepared in good yields and characterized by spectroscopic methods. The structure of 1 was determined by single-crystal X-ray diffraction structural analysis. The structure shows two kinds of whole-molecule disorder: the ester molecule statistically occupies two different sites in the crystal asymmetric unit with occupancies of 95 and 5 % (positional disorder), and at each of the sites there is additional disorder over a crystallographic 2-fold rotation axis (orientational disorder). Analysis of diffuse scattering patterns in the diffraction images revealed the positional disorder as stacking disorder of molecular layers with two-dimensional translational symmetry. In the absence of other, more directional interactions, the molecules in the crystal structure of 1 are held together only by van der Waals interactions which provide the rationale for the observed whole-molecule disorder.
- Milic, Dalibor,Aleskovic, Marija,Matkovic-Calogovic, Dubravka,Mlinaric-Majerski, Kata
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experimental part
p. 833 - 839
(2010/03/25)
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- Carbenes in polycyclic systems: Generation and fate of potential adamantane-1,3-dicarbenes
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Potential formation and reactions of adamantane-1,3-dicarbenes 1-3 generated under different conditions and from different precursors, such as sodium salt of adamantane-1,3-dicarbaldehyde ditosylhydrazone (4a), sodium salt of 1,3-diacetyladamantane ditosylhydrazone (5a), sodium salt of 1,3-dibenzoyladamantane ditosylhydrazone (6a), and 1,3-bis(diazobenzyl) adamantane (7) are reported. Carbene species generated thermally from 4a yielded bishomoa-damantane (15), as a final product, via intramolecular insertion into adjacent C - C bond and formation of putative anti-Bredt olefin species, followed by hydrogen abstraction. Pyrolysis of the same sodium salt 4a in the presence of hydrogen donor n-Bu3SnH afforded 1,3-dimethyladamantane (17). Thermal decomposition of sodium salt 5a afforded 1,3-divinyladamantane (14). However, thermal decomposition of sodium salt 6a and diazo-precursor 7 gave benzonitrile as a sole identified product. On the contrary, photolysis of 7 afforded dimeric azine 21. Finally, the synthetic pathways of novel tosylhydrazone derivatives 4, 5, 6 and their corresponding sodium salts, as well as bis-diazocompound 7 are described. Copyright
- Klaic, Lada,Aleskovic, Marija,Veljkovic, Jelena,Mlinaric-Majerski, Kata
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p. 299 - 305
(2008/09/20)
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- NOVEL ADAMANTANE DERIVATIVE
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There is provided a trisadamantane based compound which is useful not only as a photoresist additive but also as pharmaceuticals, an agrochemical intermediate, a resin additive (heat resistance improver) and the like, and which is represented by the general formula (I) wherein R1 and R2 are each an alkyl group having 1 to 8 carbon atoms; X1 and X2 are each hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, carboxyl group or COOR3 in which R3 is an alkyl group having 1 to 8 carbon atoms.
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- Positive modulators of nicotinic receptor agonists
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Compounds of Formula I wherein R1a, R1b, R2b, R3b, R3a, R2a, B1, B2, Z, A2and A1are as defined in the specification, enantiomers thereof, pharmaceutically-acceptable salts thereof, processes for preparing them, pharmaceutical compositions containing them and their use in therapy, especially for treatment of conditions associated with reductions in nicotinic transmission. Compounds of the invention enhance the efficacy of agonists at nicotinic receptors.
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Page column 11
(2008/06/13)
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- Process for producing t-butyl esters of bridged-ring polycarboxylic acids
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In a process of the present invention for producing a bridged cyclic polycarboxylic acid t-butyl ester, a bridged cyclic polycarboxylic halide of following Formula (1): (wherein ring Z is a bridged cyclic carbon ring; X is a halogen atom; and m denotes an integer of 2 or more, where ring Z may have a substituent) is allowed to react with t-butyl alcohol or its alkali metal salt to thereby yield an ester of following Formula (2): (whereintBu is a t-butyl group; and ring Z and m have the same meanings as defined above.) This process can commercially efficiently produce a bridged cyclic polycarboxylic acid t-butyl ester. The compound of Formula (1) can be prepared by allowing a bridged cyclic polycarboxylic acid of following Formula (3): (wherein ring Z is a bridged cyclic carbon ring; and m denotes an integer of 2 or more, where ring Z may have a substituent) to react with a halogenating agent.
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- Preparation and 13C NMR Spectroscopic Study of Disubstituted Adamantane-1,3-dimethyldiyl Dications
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A series of substituted adamantane-1,3-dimethyldiyl dications 5 has been prepared by the ionization of α,α,α',α'-tetrasubstituted-1,3-adamantanedimethyl diols 6 in superacidic media.The dications were stable with groups such as phenyl and methyl, however, unstable with cyclopropyl groups.The 13C NMR spectroscopic study of the obtained dications clearly indicates that the positive charges are more delocalized into the substituents due to the close proximity of the cationic centers through the adamantyl cage.These studies are informative in probing cage compounds with multiply-charged centers.
- Heagy, Michael D.,Wang, Qi,Olah, George A.,Prakash, G. K. Surya
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p. 7351 - 7354
(2007/10/03)
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