27318-28-1Relevant articles and documents
Modified Fullerenes for Efficient Electron Transport Layer-Free Perovskite/Fullerene Blend-Based Solar Cells
Sandoval-Torrientes, Rafael,Pascual, Jorge,García-Benito, Inés,Collavini, Silvia,Kosta, Ivet,Tena-Zaera, Ramón,Martín, Nazario,Delgado, Juan Luis
, p. 2023 - 2029 (2017)
A variety of novel chemically modified fullerenes, showing different electron-accepting capabilities, has been synthesized and used to prepare electron transport layer (ETL)-free solar cells based on perovskite/fullerene blends. In particular, isoxazolino[60] fullerenes are proven to be a good candidate for processing blend films with CH3NH3PbI3 and obtaining enhanced power conversion efficiency (PCE) ETL-free perovskite solar cells (PSCs), improving the state-of-the-art PCE (i.e., 14.3 %) for this simplified device architecture. A beneficial effect for pyrazolino and methano[60]fullerene derivatives versus pristine [60]/fullerene is also shown. Furthermore, a clear correlation between the LUMO energy level of the fullerene component and the open circuit voltage of the solar cells is found. Apart from the new knowledge on innovative fullerene derivatives for PSCs, the universality and versatility of perovskite/fullerene blend films to obtain efficient ETL-free PSCs is demonstrated.
Triazole alcohol derivative as well as preparation method and application thereof
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Paragraph 0223-0224, (2020/03/11)
The invention relates to a triazole alcohol derivative as well as a preparation method and application thereof. The chemical structure of the triazole alcohol derivative is shown as a formula I, R1 represents a benzene ring or a substituted benzene ring, and substituent groups of the substituted benzene ring can be located at all positions of the benzene ring, can be mono-substituted or multi-substituted, and can be selected from a) halogen which is F and Cl; b) an electron withdrawing group which is cyano or trifluoromethyl; c ) a lower alkyl of 1-4 carbon atoms or a halogen substituted loweralkyl; and d) lower alkoxy of 1-4 carbon atoms or halogen substituted lower alkoxy. The compound of the invention has strong antifungal activity, has the advantages of low toxicity, wide antibacterial spectrum and the like, and can be used for preparing antifungal drugs.
Design, synthesis, and in vitro evaluation of novel triazole analogues featuring isoxazole moieties as antifungal agents
Chai, Xiaoyun,Ding, Zichao,Hao, Yumeng,Jiang, Yuanying,Jin, Yongsheng,Ni, Tingjunhong,Wang, Ruilian,Wang, Ruina,Wang, Ting,Xie, Fei,Yu, Shichong,Zhang, Dazhi
supporting information, (2020/06/17)
In order to develop novel antifungal agents, based on our previous work, a series of (2R,3R)-3-((3-substitutied-isoxazol-5-yl)methoxy)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol (a1-a26) were designed and synthesized. All of the compounds exhibited good in vitro antifungal activities against eight human pathogenic fungi. Among them, compound a6 showed excellent inhibitory activity against Candida albicans and Candida parasilosis with MIC80 values of 0.0313 μg/mL. In addition, compounds a6, a9, a12, a13 and a14 exhibited moderate inhibitory activities against fluconazole-resistant isolates with MIC80 values ranging from 8 μg/mL to 16 μg/mL. Furthermore, compounds a6, a12 and a23 exhibited low inhibition profiles for CYP3A4. Clear SARs were analyzed, and the molecular docking experiment was carried out to further investigate the relationship between a6 and the target enzyme CYP51.
Betulinic acid derivatives: a new class of α-glucosidase inhibitors and LPS-stimulated nitric oxide production inhibition on mouse macrophage RAW 264.7 cells
Gundoju, Narayanarao,Bokam, Ramesh,Yalavarthi, Nageswara Rao,Azad, Rajaram,Ponnapalli, Mangala Gowri
supporting information, p. 2618 - 2622 (2018/04/30)
Chemical manipulation studies were conducted on betulinic acid (1), twenty-one new rationally designed analogues of 1 with modifications at C-28 were synthesized for their evaluation of inhibitory effects on α-glucosidase and LPS-stimulated nitric oxide production in mouse macrophage RAW 264.7 cells. Compound 2 (IC50 = 5.4 μM) exhibited an almost 1.4-fold increase in α-glucosidase inhibitory activity on yeast α-glucosidase while analogues 5 (IC50 16.4 μM) and 11 (IC50 16.6 μM) exhibited a 2-fold enhanced inhibitory activity on NO-production than betulinic acid.
Postsynthetic Modification of Metal-Organic Frameworks through Nitrile Oxide-Alkyne Cycloaddition
Von Zons, Tobias,Brokmann, Luisa,Lippke, Jann,Preu?e, Thomas,Hülsmann, Miriam,Schaate, Andreas,Behrens, Peter,Godt, Adelheid
supporting information, p. 3348 - 3359 (2018/03/25)
Postsynthetic modification of metal-organic frameworks is an important method to tailor their properties. We report on the nitrile oxide-alkyne cycloaddition (NOAC) as a modification tool, a reaction requiring neither strained alkynes nor a catalyst. This is demonstrated with the reaction of nitrile oxides with PEPEP-PIZOF-15 and -19 at room temperature. PIZOF-15 and -19 are porous Zr-based MOFs (BET surface areas 1740 and 960 m2 g-1, respectively) consisting of two mutually interpenetrating UiO-type frameworks with linkers of the type -O2C[PE-P(R1,R2)-EP]CO2- (P, phenylene; E, ethynylene; R1 and R2, side chains at the central benzene ring with R1 = R2 = OCH2C≡CH or R1 = OCH2C≡CH and R2 = O(CH2CH2O)3Me). Their syntheses, using benzoic acid as a modulator, and their characterization are reported herein. The propargyloxy (OCH2C≡CH) side chains contain the ethyne moieties needed for NOAC. Formation of nitrile oxides through oxidation of oximes in aqueous ethanolic solution in the presence of PEPEP-PIZOF-15 and -19 resulted in the reaction of 96-100% of the ethyne moieties to give isoxazoles. Thereby the framework was preserved. The type of nitrile oxide RCNO was greatly varied with R being isopentyl, tolyl, 2-pyridyl, and pentafluorophenyl. A detailed NMR spectroscopic investigation showed the formation of the 3,5-disubstituted isoxazole to be clearly favored (≥96%) over that of the constitutional isomeric 3,4-disubstituted isoxazole, except for one example.
Structural and morphological aspects of small 3,5-disubstituted isoxazoles
Lopes, Luana D.,Bortoluzzi, Adailton J.,Prampolini, Giacomo,dos Santos, Francisco P.,Livotto, Paolo R.,Merlo, Aloir A.
, p. 24 - 36 (2018/04/23)
The structural and morphological features of small 3,5-disubstituted isoxazoles/isoxazolines are presented and discussed in the light of thermal analysis by differential scanning calorimetry (DSC), polarized optical microscopy (POM) technique, combined with single crystal X-ray diffraction and molecular modeling. The title compounds obtained were also characterized by 1H, 13C and 19F NMR. Two of the 3,5-diarylisoxazoles reported here contain totally hydrogenated or fluorinated benzene rings on both sides of the heterocycle. Partially hydrogenated and fluorinated molecules were prepared alternating the position of the benzene rings on 3- and 5-position of the isoxazoles. Other isoxazoles were synthesized to compare the influence of fluorine atoms on the transitional properties. They were synthesized in two steps, starting from [3 + 2] 1,3-dipolar cycloaddition reaction of nitrile oxides with alkenes to yield the isoxazolines and subsequent MnO2-oxidation process to reach the final isoxazoles.
A versatile and green mechanochemical route for aldehyde-oxime conversions
Aakeroey, Christer B.,Sinha, Abhijeet S.,Epa, Kanishka N.,Spartz, Christine L.,Desper, John
supporting information, p. 11289 - 11291,3 (2012/12/12)
A robust, facile and solvent-free mechanochemical path for aldehyde-oxime transformations using hydroxylamine and NaOH is explored; the method is suitable for aromatic and aliphatic aldehydes decorated with a range of substituents. This journal is
Ruthenium-catalyzed rearrangement of aldoximes to primary amides in water
Garcia-Alvarez, Rocio,Diaz-Alvarez, Alba E.,Borge, Javier,Crochet, Pascale,Cadierno, Victorio
, p. 6482 - 6490 (2012/10/30)
The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70-90%) after short reaction times (1-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes and tolerated several functional groups. Reaction profiles and experiments using 18O-labeled water indicate that two different mechanisms are implicated in these transformations. In both of them, nitrile intermediates are initially formed by dehydration of the aldoximes. These intermediates are then hydrated to the corresponding amides by the action of a second molecule of aldoxime or water. A kinetic analysis of the rearrangement of benzaldoxime to benzamide is also discussed.
Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning
Timperley, Christopher M.,Banks, R. Eric,Young, Ian M.,Haszeldine, Robert N.
, p. 541 - 547 (2011/09/15)
Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pKa) and second-order rate constants (kox-) of the fluorinated pyridinealdoximes towards sarin were measured. 2,3,5,6-Tetrafluoropyridine-4- aldoxime had the best profile: its kox- approached that of the therapeutic oxime P2S (310 vs. 120 l mol-1 min-1), but its higher pKa (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK a nearer to 8 and enhance their therapeutic potential. Crown Copyright
Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes
Jawalekar, Anup M.,Reubsaet, Erik,Rutjes, Floris P. J. T.,Van Delft, Floris L.
supporting information; experimental part, p. 3198 - 3200 (2011/05/05)
Treatment of oximes with hypervalent iodine leads to substituted isoxazoles via rapid formation of nitrile oxides. Reaction with terminal alkynes led to a series of 3,5-disubstituted isoxazoles with complete regioselectivity and high yield, in a procedure
