122406-45-5Relevant articles and documents
Selective etherification of calix[4]arenes
Wang, Wen-Guang,Zheng, Qi-Yu,Huang, Zhi-Tang
, p. 3711 - 3718 (1999)
Calix[4]arenes 1 or 2 react with alkyl halides and aqueous potassium hydroxide in the presence of PEG as phase transfer catalyst at room temperature to give the selectively distally dietherified product 3 or 4 in excellent yields. While at the same reacti
Influence of laterally attached alkyl groups on the conformational behaviour of a basic calix[4]arene: Combined NMR, molecular mechanics and X-ray study
Gruner, Margit,Fischer, Conrad,Gruber, Tobias,Weber, Edwin
, p. 256 - 266 (2010)
Three new calixarenes 3-5 featuring an alkyl residue of different chain lengths attached to one of the central ring methylene groups of the basic calix[4]arene 1 have been prepared. A systematic study that includes also the lower homologous compound 2 showing the effect of the alkyl substitution on the conformational behaviour of the calixarene framework in comparison with the unsubstituted parent compound 1 is reported. The application of special 2D NMR techniques, 2D-EXSY and ROESY methods at various temperatures establishes that calixarenes 2-5 adopt the partial cone conformation of lower symmetry and far less the symmetric cone and 1,2-alternate conformations. In solution, they undergo a fast interconversion with relatively low activation energies of about 15 kcal/mol at room temperature. The conformer distribution is well reproduced by molecular mechanistic calculations (MMFF94), indicating the present conformers to assume the lowest steric energies. A single-crystal X-ray structure of the lateral ethyl derivative 2 corroborates these results, showing the molecule in a sterically favourable partial cone conformation.
Calorimetric investigation of nano-basket's binding
Mokhtari, Bahram,Pourabdollah, Kobra
, p. 13 - 18 (2013)
Eleven scaffolds of di-ionizable calix[4]arene conformers bearing two pendant groups of N-phenyl-sulfonyl carboxamides were synthesized and examined using isothermal titration calorimetry. The binding mechanisms of those conformers towards alkali metal ca
Turn on fluorescence strip based sensor for recognition of Sr2+ and CN? via lowerrim substituted calix[4]arene and its computational investigation
Sutariya, Pinkesh G.,Soni, Heni,Gandhi, Sahaj A.,Pandya, Alok
, (2020)
Fluorescence sensor L designed around a calix[4]arene scaffold, bearing two fluorogenic aminoquinoline moities, has been synthesized. It is found to be selective and sensitive towards Sr2+ and CN? over a wide range of cations and anions in a spectrofluorometric study in acetonitrile. The ion-binding property of L was monitored by fluorescence spectroscopy, UV–vis spectroscopy, ESI-MS, 1H NMR, FT-IR investigation and PXRD study. The host L shows a minimum detection limit which is 1.36 nM for Sr2+ and 1.23 nM for CN? having concentration range 5–120 nM and 5–115 nM respectively. The calculated binding constants for L:Sr2+ and L: CN? are respectively 8.859 × 108 M?1 and 8.574 × 108 M?1. Our host L has been utilised in formation of a user-friendly, affordable, and disposable paper-based analytical device (PAD) for rapid chemical screening of Sr2+ and CN? ion via single strip. Moreover, the optimization of probe L has also been done by the MOPAC-2016 software package using NM7 popular method resulting ?21.71 kcals/mol heat of formation and also determined the HOMO-LUMO energy band gap for L, L:Sr2+ and L: CN?. Further, molecular docking score has been calculated using HEX software. The applicability of our probe in real samples containing Sr2+ and CN? has also been checked by emission study with 94–99% recovery.
Synthesis of novel calix[4]arene: P -benzazole derivatives and investigation of their DNA binding and cleavage activities with molecular docking and experimental studies
Aksakal, Fatma,Ozkan, Seyda Cigdem,Yilmaz, Aydan
, p. 38695 - 38708 (2020)
In this study, novel p-benzimidazole-derived calix[4]arene compounds with different structures, and a benzothiazole-derived calix[4]arene compound, were synthesized by a microwave-assisted method and their structures were determined by FTIR, 1H NMR, 13C NMR, MALDI-TOF mass spectroscopy, and elemental analysis. The effects of functional calixarenes against bacterial (pBR322 plasmid DNA) and eukaryotic DNA (calf thymus DNA = CT-DNA) were investigated. The studies with plasmid DNA have shown that compounds 6 and 10 containing methyl and benzyl groups, respectively, have DNA cleavage activity at the highest concentrations (10 000 μM). Interactions withplasmid DNA using some restriction enzymes (BamHI and HindIII) were also investigated. The binding ability of p-substituted calix[4]arene compounds towards CT-DNA was examined using UV-vis and fluorescence spectroscopy and it was determined that some compounds showed efficiency. In particular, itwas observed that the functional compounds (10 and 5) containing benzyl and chloro-groups had higher activity (Kb binding constants were found to be 7.1 × 103 M-1 and 9.3 × 102 M-1 respectively) on DNA than other compounds. Competitive binding experiments using ethidium bromide also gave an idea about the binding properties. Docking studies of the synthesized compounds with DNA were performed to predict the binding modes, affinities and noncovalent interactions stabilizing the DNA-compound complexes at the molecular level. Docking results were in good agreement with the experimental findings on the DNA binding activities of compounds. Based on these results, this preliminary study could shed light on future experimental antibacterial and/or anticancer research.
Preparation and sensor evaluation of a Pacman phthalocyanine
O'Malley, Shane,Schazmann, Benjamin,Diamond, Dermot,Nolan, Kieran
, p. 9003 - 9007 (2007)
We report both the preparation and sensor evaluation of a new metal-free calixarene bridged binuclear phthalocyanine.
Ring a bell: Disubstituted calix[4]arene as ligand for transition metal chlorides
Crochet, Aurelien,Fromm, Katharina M.
, p. 610 - 616 (2013)
Lower rim 1,3-disubstituted p-tert-butylcalix[4]arene is studied here in its deprotonated form as complexing ligand for iron and chromium chloride. Crystallization of the two complexes from dry THF gives two different stoichiometries and structures, a trinuclear iron compound and a second, mononuclear structure with chromium. In both cases, the ligand adopts an elliptical shape and the metal ions are bound to the lower rim of the calixarene molecule.
Regioselective ipso formylation of p-tert-butylcalix[4]arene
Chawla,Pant,Srivastava, Bindu
, p. 7259 - 7262 (2005)
A convenient procedure for direct introduction of one formyl group into p-tert-butylcalix[4]arenes through ipso substitution is described.
Evaluation of calix[4]arene-based chiral diphosphite ligands in Rh-catalyzed asymmetric hydrogenation of simple dehydroamino acid derivatives
Liu, Shasha,Sandoval, Christian A.
, p. 65 - 72 (2010)
The versatile calix[4]arene framework yielded chiral diphosphite ligands applicable for Rh-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives. Optimum efficiency was obtained for: R1 =-C(CH 3)3; R2/s
Fluorescent Calixarene which responds to Solvent Polarity and Metal Ions
Aoki, Izuo,Kawabata, Hirosuke,Nakashima, Kazuaki,Shinkai, Seiji
, p. 1771 - 1773 (1991)
A calixarene having two pyrene moieties on the lower rim has been synthetized; the ratio of the monomer vs. excimer emission was sensitively affected by solvent polarity and added metal ions.
