2958-72-7Relevant academic research and scientific papers
N-substituted 8-aminopentacyclo[5.4.0.02,6.03,10. 05,9]undecanes as σ receptor ligands with potential neuroprotective effects
Banister, Samuel D.,Manoli, Miral,Barron, Melissa L.,Werry, Eryn L.,Kassiou, Michael
, p. 6038 - 6052 (2013)
Several libraries of similarly N-substituted 8-aminopentacyclo[5.4.0.0 2,6.03,10.05,9]undecanes (9), N-methyl-8-aminopentacyclo[5.4.0.02,6.03,10.0 5,9]undecanes (14), and N-methyl-11-aminop
Barriers to Intramolecular Hydride Transfers in Some Polycyclic Hydroxyketones
Craze, Gabrielle-Anne,Watt, Ian
, p. 175 - 184 (1981)
The hydroxyketones (1) and (2) have been prepared from the Diels-Alder adducts of p-benzoquinone with cyclopentadiene and cyclohexa-1,3-diene.The boron trifluoride-ether catalysed reaction of cyclohepta-1,3-diene with p-benzoquinone gave good yields of the Diels-Alder adduct which was converted into hydroxyketone (3).Experiments with cyclohexanol and admantan-2-ol established characteristic 13C n.m.r. chemical shifts associated with deprotonation of alcohols by dimsyl sodium in dimethyl sulphoxide.Solutions of the sodium salts of (1)-(3) were prepared and dynamic 13C n.m.r. spectroscopy gave barriers for their degenerate rearrangement of >21.7 (100 deg C), 19.0 (100 deg C), and 17.3 (72 deg C) kcal mol-1, respectively.The relationship between variation of barrier and molecular geometry is discussed with the aid of empirical force field calculations.
Synthesis and Biological Evaluation of Pentacycloundecylamines and Triquinylamines as Voltage-Gated Calcium Channel Blockers
Young, Lois-May,Geldenhuys, Werner J.,Domingo, Olwen C.,Malan, Sarel F.,Van Der Schyf, Cornelis J.
, p. 252 - 267 (2016)
Preclinical studies for neurodegenerative diseases have shown a multi-targeted approach to be successful in the treatment of these complex disorders with several pathoetiological pathways. Polycyclic compounds, such as NGP1-01 (7a), have demonstrated the ability to target multiple mechanisms of the complex etiology and are referred to as multifunctional compounds. These compounds have served as scaffolds with the ability to attenuate Ca2+ overload and excitotoxicity through several pathways. In this study, our focus was on mitigating Ca2+ overload through the L-type calcium channels (LTCC). Here, we report the synthesis and biological evaluation of several novel polycyclic compounds. We determined the IC50 values for both the pentacycloundecylamines and the triquinylamines by means of a high-throughput fluorescence calcium flux assay utilizing Fura-2/AM. The potential of these compounds to offer protection against hydrogen peroxide-induced cell death was also evaluated. Overall, 8-benzylamino-8,11-oxapentacyclo[5.4.0.02,6.03,10.05,9]undecane (NGP1-01, 7a) had the most favorable pharmacological profile with an IC50 value of 86 μM for LTCC inhibition and significant reduction of hydrogen peroxide-induced cell death. In general, the triquinylamines were more active as LTCC blockers than the oxa-pentacycloundecylamines. The aza-pentacycloundecylamines were potent LTCC inhibitors, with 8-hydroxy-N-phenylethyl-8,11-azapentacyclo[5.4.0.02,6.03,10.05,9]undecane (8b) also able to offer significant protection in the cell viability assays.
Synthesis of 4,4′-spirobi[pentacyclo[5.4.0.02,6.03,10.05,9]undecane]
Shi, Yijun,Jiang, Jingyang,Wang, Jianzhi,Wang, Yanhua
, p. 6704 - 6706 (2015)
4,4′-Spirobi[pentacyclo[5.4.0.02,6.03,10.05,9]undecane] (10) is first successfully prepared by a nine step synthetic scheme starting from the key intermediate (cyclopentadiene derivate, 2). This synthetic scheme avoids using the hardly obtainable spiro[4.4]nonatetraene (18) as the starting material. In the structure of 10, two polycyclic cages share one spiro-carbon so that it has high density (1.2663 g/cm3) and high volumetric heat of combustion (53.353 MJ/L).
Complete Assignment of the (1)H and (13)C NMR Spectra of a Pentacyclo2,6.03,10.05,9>undecane Derivative
Cadd, D. H.,Feast, W. J.,Kenwright, A. M.,Say, J. M.
, p. 801 - 807 (1993)
The production of compounds derived from intramolecular photocycloaddition reactions upon Diels-Alder adducts has received considerable attention, but assignment of the NMR spectra of the photoaddition products has proved problematic, rendering structural determination difficult.This paper reports the complete assignments of the proton and carbon NMR spectra of 11,11-dimethoxypentacyclo2,6.03,10.05,9>undecan-8-one and the assignment of the spectra of pentacyclo2,6.03,10.05,9>undecan-8,11-dione by analogy.
A convenient road to 1-chloropentacycloundecanes - A joint experimental and computational investigation
Sharapa, Dmitry I.,Gayday, Alexander V.,Mitlenko, Alena G.,Levandovskiy, Igor A.,Shubina, Tatyana E.
, p. 2554 - 2561 (2011)
An efficient synthetic strategy to obtain 1-chloro-Cs- trishomocubane and 1-chloro-D3-trishomocubane is described. 1-Chloro-Cs-trishomocubane is synthesized by a regioselective Diels-Alder reaction, and B3PW91/6-31G(d,p) calculations offer a plausible explanation of the reaction mechanism. Surprisingly, 1-chloro-C s-trishomocubane does not undergo an acid-catalyzed rearrangement to form 1-chloro-D3-trishomocubane and was obtained by chlorosulfation of Cookson's diketone. A possible mechanism of the reaction involving the formation of Cs- and D3-trishomocubane nonclassical cations was proposed on the basis of a mechanistic [B3PW91/6-31G(d,p) and MP2/cc-pVDZ] study. An efficient method to prepare 1-substituted pentacycloundecanes is described. Simple modification of the starting material for the Diels-Alder reaction gives 1-Cs-trishomocubane derivatives readily. Chlorosulfation of Cookson's diketone in four steps gives 1-chloro-D3-trishomocubane in good yields. The proposed mechanism of the reactions is explained by DFT and MP2 calculations. Copyright
Rational design of triplet sensitizers for the transfer of excited state photochemistry from UV to visible
Booker-Milburn, Kevin,Elliott, Luke D.,George, Michael W.,Kayal, Surajit
supporting information, p. 14947 - 14956 (2020/10/13)
Time Dependent Density Functional Theory has been used to assist the design and synthesis of a series thioxanthone triplet sensitizers. Calculated energies of the triplet excited state (ET) informed both the type and position of auxochromes placed on the thioxanthone core, enabling fine-tuning of the UV-vis absorptions and associated triplet energies. The calculated results were highly consistent with experimental observation in both the order of the λmax and ET values. The synthesized compounds were then evaluated for their efficacies as triplet sensitizers in a variety of UV and visible light preparative photochemical reactions. The results of this study exceeded expectations; in particular [2 + 2] cycloaddition chemistry that had previously been sensitized in the UV was found to undergo cycloaddition at 455 nm (blue) with a 2- to 9-fold increase in productivity (g/h) relative to input power. This study demonstrates the ability of powerful modern computational methods to aid in the design of successful and productive triplet sensitized photochemical reactions.
Design, synthesis and evaluation of pentacycloundecane and hexacycloundecane propargylamine derivatives as multifunctional neuroprotective agents
Zindo, Frank T.,Malan, Sarel F.,Omoruyi, Sylvester I.,Enogieru, Adaze B.,Ekpo, Okobi E.,Joubert, Jacques
, p. 83 - 94 (2018/12/04)
The multifactorial pathophysiology of neurodegenerative disorders remains one of the main challenges in the design of a single molecule that may ultimately prevent the progression of these disorders in affected patients. In this article, we report on twelve novel polycyclic amine cage derivatives, synthesized with or without a propargylamine function, designed to possess inherent multifunctional neuroprotective activity. The MTT cytotoxicity assay results showed the SH-SY5Y human neuroblastoma cells to be viable with the twelve compounds, particularly at concentrations less than 10 μM. The compounds also showed significant neuroprotective activity, ranging from 31% to 61% at 1 μM, when assayed on SH-SY5Y human neuroblastoma cells in which neurodegeneration was induced by MPP+. Calcium regulation assays conducted on the same cell line showed the compounds to be significant VGCC blockers with activity ranging from 26.6% to 51.3% at 10 μM; as well as significant NMDAr antagonists with compound 5 showing the best activity of 88.3% at 10 μM. When assayed on human MAO isoenzymes, most of the compounds showed significant inhibitory activity, with compound 5 showing the best activity (MAO-B: IC50 = 1.70 μM). Generally, the compounds were about 3–52 times more selective to the MAO-B isoenzyme than the MAO-A isoenzyme. Based on the time-dependency studies conducted, the compounds can be defined as reversible MAO inhibitors. Several structure activity relationships were derived from the various assays conducted, and the compounds’ possible putative binding modes within the MAO-B enzyme cavity were assessed in silico.
UV PhotoVap: Demonstrating How a Simple and Versatile Reactor Based on a Conventional Rotary Evaporator Can Be Used for UV Photochemistry
Clark, Charlotte A.,Lee, Darren S.,Pickering, Stephen J.,Poliakoff, Martyn,George, Michael W.
supporting information, p. 595 - 599 (2018/08/17)
We report the use of a simple rotary evaporator as a semi-continuous UV photochemical reactor. By generation of a thin film from the rotation of a flask, better light penetration is achieved, and in this work we used high-power Hg lamps to enable the direct irradiation of molecules with UV light. The intramolecular [2 + 2] photocycloaddition of Cookson's dione and the intermolecular [2 + 2] photocycloaddition of maleimide with 1-hexyne were used as test reactions to examine the effectiveness of this reactor. High productivities, equivalent to 210 g h-1, were obtained for the simple intramolecular reaction, demonstrating the scalability of the reactor. The effects of flask size, reaction mixture volume, and use of borosilicate or quartz glassware were also investigated.
A Small-Footprint, High-Capacity Flow Reactor for UV Photochemical Synthesis on the Kilogram Scale
Elliott, Luke D.,Berry, Malcolm,Harji, Bashir,Klauber, David,Leonard, John,Booker-Milburn, Kevin I.
supporting information, p. 1806 - 1811 (2016/10/31)
The development of a highly compact and powerful reactor for synthetic organic photochemistry is described enabling a 10-fold reduction in reaction times, with up to 30% more power efficiency than previous fluorinated ethylene propylene tube reactors. Two
