423176-32-3Relevant academic research and scientific papers
Chemical speciation of copper(II) diaminediamide derivative of pentacycloundecane - A potential anti-inflammatory agent
Odisitse, Sebusi,Jackson, Graham E.,Govender, Thavendran,Kruger, Hendrik G.,Singh, Amith
, p. 1140 - 1149 (2007)
Formation constants of copper(ii), zinc(ii) and calcium(ii) with 3,5-diaminodiamido-4-oxahexacyclododecane (cageL) has been studied by glass electrode potentiometry at 25 °C and an ionic strength of 0.15 mol dm -3. Copper(ii) forms more stable complexes with cageL than zinc(ii) and calcium(ii). Metal ion complexation promotes deprotonation and coordination of the amide nitrogens resulting in overall tetragonal coordination of Cu 2+ suggested by the UV-visible electronic spectra. Speciation calculations using a blood plasma model suggest that zinc(ii) and calcium(ii) are good competitors of copper(ii) in vivo. Bio-distribution experiments using 64Cu-labelled Cu(ii)-cageL show that about 50% dose of the complex is retained in the body after 24 h. This journal is The Royal Society of Chemistry.
Facile Synthesis of Hydroxy-Substituted Thiacrown Ethers via Nucleophilic Ring Opening of Epoxides
Stefaniak, Monika,Romański, Jaros?aw
, p. 2214 - 2220 (2019/05/10)
The title thiacrown ethers were prepared in a one-step procedure to give a series of unique macrocycles possessing two unsubstituted hydroxy groups that can be easily functionalized. In addition, epoxides and macrocycles derived from Cookson's birdcage diketone, were prepared. The nucleophilic ring opening of epoxides synthesis can be classified in the frame of click chemistry. Surprisingly, some of the prepared allyl substituted polyglycols as well as bis-epoxides, especially sulfur analogues, were prepared for the first time.
Pentacyclo-undecane derived cyclic tetra-amines: Synthesis and evaluation as potent anti-tuberculosis agents
Onajole, Oluseye K.,Govender, Karnishree,Govender, Patrick,van Helden, Paul D.,Kruger, Hendrik G.,Maguire, Glenn E.M.,Muthusamy, Karen,Pillay, Manormoney,Wiid, Ian,Govender, Thavendran
scheme or table, p. 4297 - 4305 (2010/02/27)
As part of an ongoing effort to develop highly potent anti-tuberculosis agents, fourteen pentacyclo-undecane (PCU) tetra-amine compounds were synthesized and screened for their in vitro anti-mycobacterial activity against two TB strains, H37Rv and XDR 194 [an extensively drug-resistant strain of tuberculosis]. Using the broth macrodilution method, nitrofuranylamide based compounds (6a and 6b) showed almost similar activities against the H37Rv strain of Mycobacterium tuberculosis when compared with the control drug, ethambutol. N-Geranyl piperazine PCU (8a) and trans-trans farnesyl piperazine PCU (8b) were 3.2 and 3.7 times more potent than commercially available ethambutol. Both isoprenyl PCU tetra-amine derivatives and N-decyl piperazine PCU (9a) were highly active against the XDR 194 strain of tuberculosis with MICs in the range of 0.63-3.02 μM. Cytotoxicities (IC50) of isoprenyl based compounds (8a, 8b) and compound 9a were tested on a mammalian cell line [MDBK (Madin Darby bovine kidney epithelium)] with values of 30, 24 and 25 μM respectively.
NMR analysis of some pentacycloundecanedione derivatives
Kruger, Hendrik G.,Ramdhani, Reshika
, p. 71 - 74 (2007/10/03)
The complete NMR elucidation of four pentacycloundecanedione (PCUdione) derivatives is described. Major proton shifts occur when additions are performed on the carbonyl carbons. Some of the carbon signals are also transposed. Despite the fact that the signals of the methine protons on the cage skeleton experience major overlapping, complete assignment of all the protons is possible through 2D NMR experiments. Nuclear Overhauser Effect Spectroscopy (NOESY) interaction between the two nonequivalent bridge protons and protons on the cage skeleton proved to be a very convenient handle to elucidate the structures of the PCU compounds. A density functional theory (DFT) optimization [B3LYP/6-31+G(d)] of two possible ketal conformations was used to assist with the elucidation of the asymmetric ketal structure.
Synthesis, alkali metal picrate extraction, and alkali metal cation binding selectivities of some new cage-annulated polyoxamacrocyclic crown ethers
Marchand, Alan P.,Huang, Zilin,Chen, Zhibing,Hariprakasha,Namboothiri,Brodbelt, Jennifer S.,Reyzer, Michelle L.
, p. 1361 - 1368 (2007/10/03)
Five new cage-annulated crown ethers, i.e., 4a, 4b, 6b, 11a, and 11b, have been synthesized and their respective alkali metal picrate extraction profiles along with that of a previously synthesized host molecule, 6a, have been obtained. These results are compared with the corresponding results obtained for electrospray ionization mass spectrometric (ESI-MS) measurements of relative binding selectivities displayed by the same hosts toward a series of alkali metal chlorides. Among the crown-5 hosts studied, 6a displays enhanced avidity toward complexation with K+ picrate in liquid-liquid extraction experiments. Among the three crown-6 hosts, 4b proved to be the best alkali metal picrate extractant and displayed significant levels of avidity toward complexation with the larger alkali metal cations (i.e., K+, Rb+, and Cs+). The trends in the picrate extraction and the ESI-MS results obtained herein show several notable similarities and some differences. The similarities generally stem from size-selective binding properties that are intrinsic to the different cavity sizes of the cage-annulated macrocycles, whereas the differences reflect the important influence of solvation effects on the binding properties of the macrocycles.
